Author Topic: Who's had a successful Second Act careerwise?  (Read 3964 times)

Nick_Miller

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Who's had a successful Second Act careerwise?
« on: March 23, 2025, 03:35:23 PM »
I feel I'm at a crossroads. I'm 50ish, and I've worked in the legal field for over 20 years (lawyer). I'm just tired of it. And I keep thinking of other paths I might enjoy more over the next decade.

I feel that I have a limited window to pursue other careers, because of age and energy, and just because of the time it takes to build a runway/learn the ropes in a new field. My family is closing in on $1M net worth, and while that's not enough to retire on, it's enough to let me explore different career options now in my 50s.

1) Teaching. I taught before for a couple of years when I was younger. For lots of reasons, I went back into law. But I have a teaching cert still (long story, but it's good for 2 more years) and my own kids are much older now and require much less work. I'm wondering if the time is right to give education another shot? (I subbed recently for about 9 months between law jobs and enjoyed it). The pay would be about half of my current pay, and I'd basically have to teach through my 50s to make this make sense.
I'm wiser now, and more experienced, but do I have the energy?

2) Personal Training. I've gotten in good shape in recent months and I'm really giving a lot of thought to personal training. This idea is clearly a lot less developed than the teaching one, but I've been into strength training off and on since law school. I feel I can relate to a lot of potential clients (overworked parents). I'd do fine passing some certification exams, and honestly I'd probably be very content working for $25/hour at a big box gym somewhere. I mention this because I really enjoy teaching, communicating, encouraging others. (I know personal training has a lot of "sales" elements but I'd probably be ok at that too). But again, age is working against me here. It's not like I'd want to wait another 5 years to explore this.

I'm giving these ideas some thought over the next few months but for now, I'm more interested in other peoples' stories.

Who has successfully navigated a Second Act in their 40s or 50s? What tough decisions did you have to make? What obstacles did you face? Any regrets? Or should you have done it sooner? Life is short!





« Last Edit: March 23, 2025, 03:42:58 PM by Nick_Miller »

Metalcat

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Re: Who's had a successful Second Act careerwise?
« Reply #1 on: March 23, 2025, 05:56:09 PM »
I went back to school in my 40s, fully retrained as a therapist, and launched my own practice in September.

Dee

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Re: Who's had a successful Second Act careerwise?
« Reply #2 on: March 23, 2025, 07:14:54 PM »
I've been on the look out for these kinds of stories, too, Nick_Miller, for pretty much the same reasons you're expressing: wondering if I have it in me to make a career change at about this point in my life, at age 50.

Not too long ago, when we were selling our house, I got to know our real estate agent well enough to find out it was a second career for her. She started at age 50. After working in a factory (I think) for many years before that, as a way to earn money to contribute to the household when she was raising two children. She was an excellent agent - we nicknamed her Superagent Sue. I drew a lot of inspiration from her. I mean, not enough to actually make a career change but certainly enough to know that it could be done successfully.

A cousin of mine realized she was really good at and really enjoyed visual arts in her 50s. And now runs a business running art workshops and teaching art. But I believe she still works part-time in HR as a regular day job. I don't think the art business has been sufficient to meet her financial needs on its own. So more of a hybrid scenario in terms of keeping a long-time day job p/t and pursuing a passion project as well.

My neighbour started her own business as a housecleaner in her mid-40s, after working in shipping and receiving for many years. I can't remember why she made the switch, but she is very happy with her work. She enjoys doing a really good job and seeing the results right before her eyes.

My brother-in-law retired from engineering, in his 50s, I think, and now works in a retail job to supplement income. I believe there were health reasons that prompted an early retirement from the professional job. And the retail job is a bit like a barrista FIRE-type situation, where he picked a store where he was really interested in the products. I believe he enjoys the job and the lower stress as compared to the environment with professional obligations. But I don't think he enjoys it so much that he'd keep doing it if money wasn't a concern. 

As far as lawyers/jurists with second careers at a later age, a friend of mine recently reminded me that Beverly McLachlin wrote her first novel in the mornings before heading off to her day job. As Chief Justice of Canada. Right before her mandatory retirement age of 75.

Which actually might be relevant to you as I believe you are also interested in fiction writing. You could put that in your back pocket for a third career 'till age 74 or so, as you pursue a second career from age 50 or so onwards. 

I bet you'll find all sorts of examples once you start looking.

achvfi

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Re: Who's had a successful Second Act careerwise?
« Reply #3 on: March 23, 2025, 08:41:18 PM »
I feel I'm at a crossroads. I'm 50ish, and I've worked in the legal field for over 20 years (lawyer). I'm just tired of it. And I keep thinking of other paths I might enjoy more over the next decade.

If you are about 50 and have been a lawyer for over 20 years, I think your best path for financial independence may be to continue few more years in your current job. Do what ever else you want after that instead of taking on a new career.

With million dollars in investments, assuming you and/or your partner can save 100 grand a year and with 10% returns your portfolio can reach 2.2 million dollars in 5 years. That is a great portfolio for most people. Even if you don't save any more, your portfolio will reach $1.6 M if you leave your portolio to compound.  In addition Social security is not too far away.

I know this is not point of your question and there are other choices you can make like this.

Fru-Gal

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Re: Who's had a successful Second Act careerwise?
« Reply #4 on: March 24, 2025, 01:51:15 AM »
Your 50s are an amazing time to reinvent yourself. You’re still young but also way wiser/more experienced, financially stable, and no longer have kids to support. I’m constantly reinventing myself, am in my 50s and am FIREd.

GilesMM

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Re: Who's had a successful Second Act careerwise?
« Reply #5 on: March 24, 2025, 05:11:24 AM »
Don't wait to do it - jump in and get after it.  There are zillions of success stories around this and people always say "why did I wait so long"?


Two my favorites:



Glenn Tilton had a dream to work in the airline business. A family friend told him it was a disastrous business and oil and gas would be safer, so he joined Texaco and rose to deputy Chairman after 31 years.  When Chevron bought Texaco he had a chance to retire with a handsome golden parachute.  He had already picked up his dream house in Santa Fe.  Instead, he took the CEO job at struggling United Airlines at age 54.  His dream job despite zero airline management experience!  And it turned out it was, in fact, a disastrous business and he had to battle unions and enter bankruptcy almost immediately (911 fallout).  It worked out, United merged with Continental and GT finally retired to Santa Fe.


Bob Schoellhorn was in his 60s and CEO of mega pharmaceutical Abbott Labs in Chicago when he was abruptly fired the board after a scandal.  A short battle won him a retirement award.  Completely distraught, he and wife purchased a top line RV and began wandering the country as retired "gray nomads".  Bob had done his homework, though, and selected the Cadillac of motorhomes - a Marathon coach.  On a west coast tour, he dropped by the service center (and HQ) in Eugene Oregon for service. He was so impressed with the operation, he bought 23% of it and eventually bought the rest of the company and became CEO around age 65.  He was wildly successful expanding Marathon with service centers in Texas and Florida and building the brand by organizing and attending many customer camping events himself. He loved the brand and customers couldn't get enough of him.  He finally retired at age 78.

roomtempmayo

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Re: Who's had a successful Second Act careerwise?
« Reply #6 on: March 24, 2025, 08:33:47 AM »
I know several people who were either teachers or personal trainers before 50, but got burned out and either moved to an administrative role or a different field.  I don't know anyone who has started in these fields after 50, or even after 40. 

If you really want out of the legal field and you're willing to take a salary hit, what about student support roles in a university working with either undergraduates or law students?  Those roles often involve both some one-on-one coaching, as well as some larger group teaching of study skills.

Being a law librarian seems like a great gig, too.

Working as a writer/editor for Thompson is also a common offramp, and I think they're totally virtual now.  They might come the closest to matching typical legal salaries.

Omy

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Re: Who's had a successful Second Act careerwise?
« Reply #7 on: March 24, 2025, 08:57:54 AM »
I was in IT for my first 15 work years. It was fairly lucrative, but I didn't really like it.

My then husband and I were lean FI and quit our tech jobs in our mid 30s. We took 7 years off, had some adventures, and ended up divorcing and dividing our assets in half.

Since I was no longer FI, I got my real estate license in my early 40s and worked as a realtor for 15 years. I loved it and it was my path to fat FIRE (which included meeting and marrying DH).

We could have FIREd a few years earlier, but I was building my business and really enjoyed the work. I was also a bit gun-shy about quitting prematurely. Lean FIRE coupled with a divorce made me realize that I wanted more of a stash before pulling the plug the 2nd time.

I know several attorneys who became realtors or title attorneys when they burned out on their original law careers. It's a relatively easy transition with very little money/additional education required to get started.

LifeHappens

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Re: Who's had a successful Second Act careerwise?
« Reply #8 on: March 24, 2025, 11:06:29 AM »
My spouse started a PhD at 49 and eventually went into higher ed teaching. He worked in that system for 10 years.

The best teacher I personally ever had was a police officer and transitioned to teaching.

So, in short, I think 2nd act teachers are amazing. If you feel called to it, I say go for it.

Nick_Miller

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Re: Who's had a successful Second Act careerwise?
« Reply #9 on: March 24, 2025, 11:17:18 AM »
@Metalcat  How's it going?? I know you're only 6 months in, but how are you liking it thus far? How does it compare with your previous career?

@Dee  Are you thinking of any particular fields or just sorta generally pondering things? I loved hearing those examples you gave.

@achvfi  Yeah from a numbers perspective, you are probably right. No new field I'm considering is going to pay me six figures, I get that.

@Fru-Gal  Can you give me an example? How have you changed? I'm curious in non-career stuff too, like how people in our season of life find new hobbies, friends, etc.

@GilesMM Thanks for the examples!

@roomtempmayo It's funny you mentioned the student counseling, I've looked into stuff like admissions counseling and such, but it appears to be mostly sales, and I don't have the background for an actual job training/career counseling position.

@Omy Do did you just quit being a Realtor to fully retire? Are you living the good life now?

@LifeHappens Thanks! Part of me REALLY wants to give it another shot, like I have 'unfinished business' in that field, but I also know it's probably even more stressful than my current job. I'd have to triple down and really make it my life in my early/mid 50s to get good at it. Plus, unfortunately, salary schedules are almost exclusively based on years of service, so I'd start pretty much at the bottom. My life experience wouldn't help me salarywise, but it COULD get my foot in a door if I find the right principal.


Fru-Gal

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Re: Who's had a successful Second Act careerwise?
« Reply #10 on: March 24, 2025, 11:43:21 AM »
I stay vague for privacy reasons but here are things I am pursuing/achieving in my 50s and 3 years into FIRE…

—Peak fitness (lost 15 lbs in first half of 2024, have always been a very fit/strong/active person — but there is always more you can learn about the glorious human body and all the systems/organisms running everything behind the scenes while you THINK you are in charge)
—awesome solo travel include USA Rail Pass, hostels (never done that before)
—100 mile thru-hiking with spouse (inspired and supported by @NinetyFour)
—263 miles thru-hiking (163 miles ALONE)
—tons of biking
—having a blast getting places/running errands on my e-bike
—visiting friends made online all over America for last few years including the amazing @NinetyFour
—studying online through a virtual school, made amazing friends that way
—rooming with a friend made online at a conference, having a great time!
—continuing to train my dogs and notice ever more levels of their intelligence!
—getting way better at gardening
—taking classes at community college. Didn’t make a single friend this way, surprisingly, but still found it extremely enjoyable.
—enjoying time with my now grown kids. I would like to travel with them but not sure if/when that will happen.
—helping the parental units
—there is just soooooo much to learn and there has never been a better time technology-wise to do so
—buying myself all the toys I want because I am rich and my toys are relatively inexpensive and not environmentally destructive in any way (aka do not burn fuel)

One surprising thing I have discovered about myself in FIRE is that the internal todo list never goes away. I still even get a little stressed when faced with an open day. And all my days are open LOL!

I realize you may look at this and say, yeah, but how does this apply if I’m not FIREd? Well, I was like this before, but ON TOP of all that, was the money insecurity and the corporate career BS and the people/bosses I was beholden to.

I would NEVER sacrifice my health for any kind of career. But I totally understand the feeling of “doing time” so you can hit your number and get out. It’s very seductive and out whole society is designed to convince you that’s necessary.

So, the gift of your 50s is realizing NOTHING MATTERS. There are no rules other than the golden one (do unto others…). And like those wonderful examples others have shared above, it’s a gift to be able to surf along and trust that LIFE WILL SHOW YOU the next wonderful thing you get to do. But only if you trust and allow it and stop clinging to the story that you have to stay in your current job.
« Last Edit: March 24, 2025, 11:48:09 AM by Fru-Gal »

roomtempmayo

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Re: Who's had a successful Second Act careerwise?
« Reply #11 on: March 24, 2025, 11:45:34 AM »

@roomtempmayo It's funny you mentioned the student counseling, I've looked into stuff like admissions counseling and such, but it appears to be mostly sales, and I don't have the background for an actual job training/career counseling position.


I'm talking about working with currently enrolled students, not admissions.  Some of that can be helping students figure out their classes and register (keyword "academic counseling"), figure out life after college ("career services"), or helping new or struggling students learn time management and study habits ("student success" and sometimes "retention").  Some jobs might want an MA in a "related field," but your JD will be fine.  Hardly anyone is formally trained at doing this stuff and none of it requires a license; it's very much learn on the job.  The Chronicle of Higher Ed has a job board, but not all jobs get posted there.  I'd set up alerts for your local schools.

Many of these jobs didn't exist 20 or 30 years ago, but there's now an army of people on campus who do this stuff.  The need has increased dramatically since the pandemic.

The paycheck will never be large, but the lifestyle seems pretty nice.  Private schools usually offer tuition benefits for you, your spouse, and any dependents.
« Last Edit: March 24, 2025, 11:54:14 AM by roomtempmayo »

Omy

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Re: Who's had a successful Second Act careerwise?
« Reply #12 on: March 24, 2025, 11:57:37 AM »
DH retired first. I was planning to keep working because it's a job you can scale up or down as you like, but DH was having so much fun that I decided to join him.

I keep my license in referral status and keep up with Continuing Ed requirements. I make $5k-$10k a year for matching clients with realtors I know - and could easily go back to Active status if I decided to work again.

Metalcat

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Re: Who's had a successful Second Act careerwise?
« Reply #13 on: March 24, 2025, 02:24:17 PM »
@Metalcat  How's it going?? I know you're only 6 months in, but how are you liking it thus far? How does it compare with your previous career?


I'm well over a year into working clinically, but I launched my own practice in September.

I made this career choice extremely carefully. I spent a few years investigating literally just about every single career option that I could physically do with extensive interviewing of people working on various professions.

I know what I like and what I don't like. For example, line you I love writing and people have constantly pushed me to get into it because I have so many published authors in my family who have done quite well with writing, I have avoided that industry like the plague.

My new career and my previous career share the exact same target client population, so that really helps utilize a ton of transferrable skills. But I don't have to commute, I don't have to do a job that is absolutely BRUTAL on my body, I have much more flexibility in my schedule and ability to take time off. I always had autonomy over those things, but the logistics of the work demanded too much structure of my time. If I take a sick day, it doesn't cause a chaotic backlog nightmare.

My new career is simply a much, much more livable one. It's very different though and less acutely exciting, but in a lot of other ways, it's more satisfying.

It also pays similar per hour and retraining only cost me mid 5 figures. I used to pay 5 figures annually for CE because of the niche area I worked in, so that's a pretty spectacular payoff as far as I'm concerned.

I also fit better in this profession. I was at a CE course for my former profession recently because I still have my license, and it really hit me how poorly I fit with that culture. It's not like I'm a natural fit in my current professional culture either, but it's a more comfortable misfit, if that makes sense.

In my former profession I was the one focused on soft skills, the patient experience, aggressively advocating for a way of practicing where maintaining excellence and ethics could be almost as profitable as unethical bullshit and corner cutting. I was in a sea of sharks constantly fighting for the integrity of the work. Lol, now I'm the profit-focused shark compared to my colleagues who are borderline terrified of even admitting that they want to make money.

Having the business background I do though has been a godsend. My career hit a level in the first 4 months that people normally take years to achieve. And that's the thing about a second career, you're never starting from zero, you always bring with you the knowledge and skills from your previous career, so that's where the countless interviews come in. I narrowed down the fields where the skills I already possessed would be an advantage in the early stages of the profession.

I'm competing with mid 20s new grads who have never made a website, never written a speck of marketing copy, never learned any formal sales pitch skills. Etc, etc.

Being a lawyer, teacher, and author gives you an enormous range of skills to draw from and build upon in a new profession. Don't feel like you need to settle for something good enough. There's something seriously awesome and interesting out there for you.

And like you, I tried something else first, something I thought I would love, and it was a disaster. Which is what pushed me to research much more thoroughly before settling on something new.

You have everything you need to find an amazing career that you love doing. It's just going to take more analysis than you may have realized.

MaybeBabyMustache

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Re: Who's had a successful Second Act careerwise?
« Reply #14 on: March 24, 2025, 04:00:05 PM »
I'll chime in, although I'm working on a pivot at the moment. I had a 25 year career at two big tech companies. I'm about to begin teaching an online marketing class for 10 weeks, 2 hours/week zoom + 2 hours/week prep. It pays $4k/session. You're not exactly going to get rich doing it, but 1) I am also interested in potentially pivoting to an education career, and this gives me a low risk chance to try it out. 2) I actually needed a bit more experience on one of the modules, and I took the class myself (for free) before teaching it, which has nicely rounded out my own experience. 3) It will look great on my resume in a variety of more traditional roles.

I'm also in the process of interviewing for roles that are more natural career extensions of what I've previously done, so for now I'm considering this a side hustle to explore a future pivot.

Dee

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Re: Who's had a successful Second Act careerwise?
« Reply #15 on: March 24, 2025, 08:18:37 PM »
To get back to your more specific interest in personal training, I think the person who leads our exercise class just started being a fitness teacher in later life, so there may be an actual example of someone starting that career as a second act. I didn't get her whole back story but what prompted a big lifestyle changed was an unfortunately long bout of Lyme disease that went undetected for way too long, following a solo through hike. And after many years of recovery, she then became ready to work again and is now leading fitness and mind activities for people with dementia and their care partners.

I mention it because it's a segment of the population you may not have thought of, but seniors and people with various mobility issues or any other type of issues - as well as the parents of school-aged children you did already think about - could be a whole other type of clientele that would fill up different parts of a schedule.

As for my own thoughts about potential second careers, I'm at the point of trying to figure out *when* and *where* I'd be able to work productively, as well as *what* I'd be able to do during that time and still have enough time and energy outside of work to enjoy my life overall. My current balance isn't working well for me because my work-from-home job is completely solo and cerebral and much of my non-paid-work time is consumed with caring for or at least being around my partner with Alzheimer's almost all the time. Ideally, I'd be looking for something with no real deadline, that occupies my hands but not my mind and that has a bit of interaction with other people built in or that I could do while I'm with my partner. Like crocheting granny squares for charity has been super to meet a lot of my needs to feel occupied and do something meaningful...but not to earn money.

G-dog

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Re: Who's had a successful Second Act careerwise?
« Reply #16 on: March 24, 2025, 09:19:54 PM »
I switched careers at 40 yo. After 15 years doing biological research, I became a patent agent.  This path became available at the corporation I was working at, had I still been working in a a academic labs, I never would have known about this option.  I retired 15 years later at 55 yo.  That was 10 years ago.

The lawyers I worked with almost all came “ in-house” from outside law firms and found that to have much better work-life balance (and no requirement to track billable hours!).  So if you can find an in-house job, you might find a few more years.

You have huge skills in distilling down a lot of info to find key issues and planning scenarios and strategies to address those issues.  That’s very transferable.

Becoming a trainer could be interesting - the trainer at my Planet Fitness is older than 55 yo.  I think some of the older clients appreciate having someone with some vintage helping them.  I take some exercise classes at a senior center - the yoga instructor is probably in her 60s, the other 2 instructors I know are in their 30s. 

Real estate or insurance could be a decent pivot for you, you’d probably easily decipher the many pages of gobbledygook in 4 point font they hand us to read and sign.

Any chance to teach in a law school? Or teach a relevant “law” class in another major (business law, criminal justice, pre-law, social justice, etc).

Telecaster

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Re: Who's had a successful Second Act careerwise?
« Reply #17 on: March 24, 2025, 10:25:46 PM »
Don't wait to do it - jump in and get after it.  There are zillions of success stories around this and people always say "why did I wait so long"?


Two my favorites:



Glenn Tilton had a dream to work in the airline business. A family friend told him it was a disastrous business and oil and gas would be safer, so he joined Texaco and rose to deputy Chairman after 31 years.  When Chevron bought Texaco he had a chance to retire with a handsome golden parachute.  He had already picked up his dream house in Santa Fe.  Instead, he took the CEO job at struggling United Airlines at age 54.  His dream job despite zero airline management experience!  And it turned out it was, in fact, a disastrous business and he had to battle unions and enter bankruptcy almost immediately (911 fallout).  It worked out, United merged with Continental and GT finally retired to Santa Fe.


Bob Schoellhorn was in his 60s and CEO of mega pharmaceutical Abbott Labs in Chicago when he was abruptly fired the board after a scandal.  A short battle won him a retirement award.  Completely distraught, he and wife purchased a top line RV and began wandering the country as retired "gray nomads".  Bob had done his homework, though, and selected the Cadillac of motorhomes - a Marathon coach.  On a west coast tour, he dropped by the service center (and HQ) in Eugene Oregon for service. He was so impressed with the operation, he bought 23% of it and eventually bought the rest of the company and became CEO around age 65.  He was wildly successful expanding Marathon with service centers in Texas and Florida and building the brand by organizing and attending many customer camping events himself. He loved the brand and customers couldn't get enough of him.  He finally retired at age 78.

I love the enthusiasm, but stepping into an airline CEO job or buying a motorhome company isn't a feasible career move for most people. 

Smokystache

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Re: Who's had a successful Second Act careerwise?
« Reply #18 on: March 25, 2025, 08:27:24 AM »
Lots of good advice already -- just to underline a couple of points:

- The most important thing is that it's obvious that you're ready for a change. You already know that -- full stop.

- Sometimes opportunities don't appear until you've taken the next step. I would agree with @Metalcat and say you should spend some time upfront learning about other opportunities ... but you may not have the time and opportunity to do that until you quit your current job. For example, I would find a personal trainer that you like and is willing to let you shadow (or at least hang around them) for a full week or more. What are their actual hours of work spent doing? But this might be hard to do while you have a FT gig.

- Make the change sooner than later. You don't sound like someone who wants to retire to a beach, plus many of your interests (teaching, writing, etc.) can easily be done into your 70s+, so you have plenty of time to "make up" any "lost" income. (Of course, if you had zero savings my advice would be different.) It's not who has the most money, it's who is living the most fulfilled life. Classic OMY stuff.

I'd recommend:
- Make sure spouse is onboard.
- Set a date to quit.
- Make a list of opportunities/career paths to investigate.
- Create a worst case scenario plan: What can I do to earn income under the circumstances that over the next X years I don't generate any income?
- Prepare financially, medically, mentally for quitting.
- Quit.
- Execute plan. Be open to whimsy and happenstance. You don't have to go all in on anything. You could take classes to become a trainer, spend 2 hours a day writing, and still look at other things. Once you see an opportunity you like, then you can hone in on more.

But the biggest thing is that you don't need any more examples of other people who have done it (although I know it helps make us more comfortable with making a BIG change). You know that you can do this. And your hard work and frugality has put you in a nice position to take the next step.


slappy

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Re: Who's had a successful Second Act careerwise?
« Reply #19 on: March 25, 2025, 09:56:46 AM »
Re: Personal training...do you follow Mindpump? They have a course specifically for trainers that helps them build their business. That might be a good investment if you decide to go that route.

G-dog

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Re: Who's had a successful Second Act careerwise?
« Reply #20 on: March 25, 2025, 11:02:42 AM »
Since you enjoy writing - have you thought about looking into being a technical writer, or proofreading, or regulatory work (compile data and write document summaries for regulatory product approval)?  Also, communications might be a good fit, might involve some public speaking / interviews

Loren Ver

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Re: Who's had a successful Second Act careerwise?
« Reply #21 on: March 26, 2025, 06:51:35 AM »
I'd like to add a few example I know of because I think they are cool :).

A friend of mine was a chemist at BigPharma.  He retired from there but he wanted to see all the wonderful medications he had made at work so he took a second career as a EMT in a hospital.  I joked with him that he really wanted to step down and relax in his old age.  He agreed.  He said it was less stressful without all the corporate meetings.  To each their own!  Now he is learning to keep bees....

His wife was a vet.  She left that role and now works as an advocate for underprivileged and/or under-resourced women that have been diagnosed with breast cancer.  She helps them through the process to make sure they are going through the care process and understand what their treatment options are, insurance, rights, help, etc. 

My dad retired from career military.  He took the test and sold insurance because he liked to help people.  That is until one day his boss told him "Your isn't to help people, it is to sell insurance."  My dad answered "That's why I don't work here anymore."  So then my dad got asked to fill the gap at a commuter college for non-traditional students teaching political science.  He did that for a few years until the dean asked him to park in the mud so the students coming in late could have a closer spot.   

There are all kinds of jobs out there, and you don't have to pick one and do it until you punch your final clock.  You might just do it for 2-3 years and then do something else.  Why not?  Get some fun skills and do something else.  Why dig a giant rut and never leave? 

Villanelle

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Re: Who's had a successful Second Act careerwise?
« Reply #22 on: March 26, 2025, 09:09:44 AM »
What about being a substitute teacher while you get a personal training gig up and running?  And/or anjunct teaching at a local university or community college? I have mentioned a million and one times on these boards that I think sub teaching is an under-appreciated mustachian gig.  Clearly it's not for everyone and pay is fairly low, but the flexibility is unmatched. 

Nick_Miller

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Re: Who's had a successful Second Act careerwise?
« Reply #23 on: March 27, 2025, 04:05:44 PM »
What about being a substitute teacher while you get a personal training gig up and running?  And/or anjunct teaching at a local university or community college? I have mentioned a million and one times on these boards that I think sub teaching is an under-appreciated mustachian gig.  Clearly it's not for everyone and pay is fairly low, but the flexibility is unmatched.

The thought has crossed my mind.

I subbed for about 6 months recently (between jobs) and really enjoyed it, although doing it almost full time was a grind. But doing it like twice a week, maybe to supplement another part-time job, would be great.

Nick_Miller

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Re: Who's had a successful Second Act careerwise?
« Reply #24 on: March 27, 2025, 04:08:54 PM »
Man, reading all of these, I keep coming back to the same question (that maybe other people in their 40s/50s are asking themselves too)...

"Do I want to tackle a new adventure while I still can, or do I want to coast to retirement and drop the mic?"

Am I the only who changes their mind every week, or every month?

Metalcat

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Re: Who's had a successful Second Act careerwise?
« Reply #25 on: March 27, 2025, 04:32:20 PM »
Man, reading all of these, I keep coming back to the same question (that maybe other people in their 40s/50s are asking themselves too)...

"Do I want to tackle a new adventure while I still can, or do I want to coast to retirement and drop the mic?"

Am I the only who changes their mind every week, or every month?

If you can figure out something you would really love, that works with your optimal lifestyle, then it's really nice to have that as an ongoing option.

I won't *need* my new career financially for very long, but I absolutely love knowing that I have this new skill set to lean on at any point of I ever want to work more.

If it's just you trading one okay job for another, but for a substantial pay cut, then it's a lot less robust or satisfying a move.

It all comes down to how much you can get out of doing something new, and what it takes to do it in the first place.
« Last Edit: March 27, 2025, 04:36:27 PM by Metalcat »

Omy

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Re: Who's had a successful Second Act careerwise?
« Reply #26 on: March 27, 2025, 05:33:39 PM »
For me, the second career was something I wanted to try because I really didn't get much satisfaction out of my IT career.

When DH was hating his job but wanted to keep building the stash, he decided that we'd get there faster if he stuck it out. For him, the firehouse of cash was more important than taking the time to find a less lucrative coast job that he might not enjoy anyway.

AuspiciousEight

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Re: Who's had a successful Second Act careerwise?
« Reply #27 on: March 27, 2025, 06:13:10 PM »
I've thought about going back to school on multiple occasions, but never have pulled the trigger.

When I was younger I really wanted to go to school to get a PhD in psychology or neuroscience. I'm far more interested in how the human brain works and how the mind works than I am interested in coding computers, but....I needed money when I was younger, and this took priority over everything else, so I reluctantly became a software developer.

Honestly I could probably still do this, but at this point in my life I feel so burnt out that when I finally pull the trigger and retire I might spend the next year staring at the wall or something.

I've taken the approach of just continuing on with my main career until retirement. It is the path of least resistance, basically ....

ETA: I still flip back and forth about going back to school at times. I guess my point on posting this is to say that you're not the only one who has these sorts of thoughts of pursuing a different career.
« Last Edit: March 27, 2025, 06:16:25 PM by AuspiciousEight »

fuzzy math

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Re: Who's had a successful Second Act careerwise?
« Reply #28 on: March 27, 2025, 10:50:13 PM »
Man, reading all of these, I keep coming back to the same question (that maybe other people in their 40s/50s are asking themselves too)...

"Do I want to tackle a new adventure while I still can, or do I want to coast to retirement and drop the mic?"

Am I the only who changes their mind every week, or every month?

How long is your coast?


imperfect

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Re: Who's had a successful Second Act careerwise?
« Reply #29 on: March 27, 2025, 11:00:10 PM »

Great topic. I'm wondering the same myself. I'm 53, have had a 25 year career in science, and I'm about 3 years from FIRE.

My original plan was to be a university professor. That got derailed along the way.

I'm pretty sure it's too late to revive that original dream, but maybe there is something in the general vicinity that I could still do? Maybe tutoring college students. Maybe teaching a course as an adjunct. Maybe developing educational software. I don't know, these are just things to jot down on an "Act 2" list for now.

SuperNintendo Chalmers

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Re: Who's had a successful Second Act careerwise?
« Reply #30 on: March 30, 2025, 03:26:25 PM »
I stay vague for privacy reasons but here are things I am pursuing/achieving in my 50s and 3 years into FIRE…

—Peak fitness (lost 15 lbs in first half of 2024, have always been a very fit/strong/active person — but there is always more you can learn about the glorious human body and all the systems/organisms running everything behind the scenes while you THINK you are in charge)
—awesome solo travel include USA Rail Pass, hostels (never done that before)
—100 mile thru-hiking with spouse (inspired and supported by @NinetyFour)
—263 miles thru-hiking (163 miles ALONE)
—tons of biking
—having a blast getting places/running errands on my e-bike
—visiting friends made online all over America for last few years including the amazing @NinetyFour
—studying online through a virtual school, made amazing friends that way
—rooming with a friend made online at a conference, having a great time!
—continuing to train my dogs and notice ever more levels of their intelligence!
—getting way better at gardening
—taking classes at community college. Didn’t make a single friend this way, surprisingly, but still found it extremely enjoyable.
—enjoying time with my now grown kids. I would like to travel with them but not sure if/when that will happen.
—helping the parental units
—there is just soooooo much to learn and there has never been a better time technology-wise to do so
—buying myself all the toys I want because I am rich and my toys are relatively inexpensive and not environmentally destructive in any way (aka do not burn fuel)

One surprising thing I have discovered about myself in FIRE is that the internal todo list never goes away. I still even get a little stressed when faced with an open day. And all my days are open LOL!

I realize you may look at this and say, yeah, but how does this apply if I’m not FIREd? Well, I was like this before, but ON TOP of all that, was the money insecurity and the corporate career BS and the people/bosses I was beholden to.

I would NEVER sacrifice my health for any kind of career. But I totally understand the feeling of “doing time” so you can hit your number and get out. It’s very seductive and out whole society is designed to convince you that’s necessary.

So, the gift of your 50s is realizing NOTHING MATTERS. There are no rules other than the golden one (do unto others…). And like those wonderful examples others have shared above, it’s a gift to be able to surf along and trust that LIFE WILL SHOW YOU the next wonderful thing you get to do. But only if you trust and allow it and stop clinging to the story that you have to stay in your current job.

I'm late to this thread but as a newish member of the 50s club, I LOVE this post!

Dee

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Re: Who's had a successful Second Act careerwise?
« Reply #31 on: March 31, 2025, 04:37:24 PM »
Here's someone starting a second act at age 40, and his list of possible careers to switch to had a lot of overlap to yours, Nick_Miller:

https://kenilgunas.substack.com/p/my-mid-life-career-pivot-part-2

Fru-Gal

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Re: Who's had a successful Second Act careerwise?
« Reply #32 on: March 31, 2025, 05:41:27 PM »
I stay vague for privacy reasons but here are things I am pursuing/achieving in my 50s and 3 years into FIRE…

—Peak fitness (lost 15 lbs in first half of 2024, have always been a very fit/strong/active person — but there is always more you can learn about the glorious human body and all the systems/organisms running everything behind the scenes while you THINK you are in charge)
—awesome solo travel include USA Rail Pass, hostels (never done that before)
—100 mile thru-hiking with spouse (inspired and supported by @NinetyFour)
—263 miles thru-hiking (163 miles ALONE)
—tons of biking
—having a blast getting places/running errands on my e-bike
—visiting friends made online all over America for last few years including the amazing @NinetyFour
—studying online through a virtual school, made amazing friends that way
—rooming with a friend made online at a conference, having a great time!
—continuing to train my dogs and notice ever more levels of their intelligence!
—getting way better at gardening
—taking classes at community college. Didn’t make a single friend this way, surprisingly, but still found it extremely enjoyable.
—enjoying time with my now grown kids. I would like to travel with them but not sure if/when that will happen.
—helping the parental units
—there is just soooooo much to learn and there has never been a better time technology-wise to do so
—buying myself all the toys I want because I am rich and my toys are relatively inexpensive and not environmentally destructive in any way (aka do not burn fuel)

One surprising thing I have discovered about myself in FIRE is that the internal todo list never goes away. I still even get a little stressed when faced with an open day. And all my days are open LOL!

I realize you may look at this and say, yeah, but how does this apply if I’m not FIREd? Well, I was like this before, but ON TOP of all that, was the money insecurity and the corporate career BS and the people/bosses I was beholden to.

I would NEVER sacrifice my health for any kind of career. But I totally understand the feeling of “doing time” so you can hit your number and get out. It’s very seductive and out whole society is designed to convince you that’s necessary.

So, the gift of your 50s is realizing NOTHING MATTERS. There are no rules other than the golden one (do unto others…). And like those wonderful examples others have shared above, it’s a gift to be able to surf along and trust that LIFE WILL SHOW YOU the next wonderful thing you get to do. But only if you trust and allow it and stop clinging to the story that you have to stay in your current job.

I'm late to this thread but as a newish member of the 50s club, I LOVE this post!

Thank you!

FLBiker

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Re: Who's had a successful Second Act careerwise?
« Reply #33 on: April 01, 2025, 08:51:51 AM »
Man, reading all of these, I keep coming back to the same question (that maybe other people in their 40s/50s are asking themselves too)...

"Do I want to tackle a new adventure while I still can, or do I want to coast to retirement and drop the mic?"

Am I the only who changes their mind every week, or every month?

If you can figure out something you would really love, that works with your optimal lifestyle, then it's really nice to have that as an ongoing option.

I won't *need* my new career financially for very long, but I absolutely love knowing that I have this new skill set to lean on at any point of I ever want to work more.

This is absolutely how I feel.  I'm 48 and we're basically at our FI number -- ~$2.5M CAD, expenses around $80K CAD, plus we get $1000 USD per month from my dad as pre-inheritance.  DW works PT earning ~$30K CAD, but her job isn't secure.  Until about a month ago, I was earning ~$100K CAD coasting in a job (business analyst) that I enjoyed well enough but certainly didn't love.  Then I was laid off (and not for poor performance, FYI :) ).

I'd been chewing over this "what's next" for years, and had decided after much deliberation that I wanted to try being an advice only financial planner, with the ultimate goal of focusing on crossborder (US / Canada) situations.  I started the coursework in the fall, and didn't really have a clear timeline, so the layoff has definitely helped push me.  I'm very grateful, though, that I was ready for the push at the time, as I think I would have really struggled if I hadn't already started down this new path.

I chose advice only financial planning for a number of reasons:
  • It's very flexible -- I could do it from any location, for whatever hours I want.  We live in a small town in Nova Scotia, so remote work is ideal.
  • The hourly rate of pay is very good -- crossborder advice only CFPs can charge $500CAD / hour and up.  I likely won't "need" the money for very long, but if the pay is good then the hours I need to work are lower.  Plus, I won't start at that rate.  I'll start as a paraplanner, then a QAFP, then, potentially, a CFP.
  • It's something I'm very passionate about.  I've spent a LOT of time learning about it on my own  (as a DIY dual-citizen crossborder investor) and I don't feel like there are a ton of great resources out there for "regular" people in this situation (folks tend to want to work with "high net worth" people).  I've helped some folks pro-bono and found it very rewarding.
  • Upon reflection, I've realized that "true" retirement isn't my goal.  My mental health is much better with some structure and some feeling of accomplishment.  I also enjoy being with people more when we're working together on projects.  I realize that there are other ways to do these things than paid work, but if I can get paid to do something I really enjoy, that seems like a good way, too.
  • The "cost of entry" is quite low.  I started doing QAFP coursework in the fall, and for all of the courses, the exam and other incidentals, I'll spend less than $5000 CAD.
  • I have always been a DIY planner, and doing it crossborder is really challenging.  I go back and forth on whether or not I should hire someone for a second opinion, so becoming a professional (and having access to a professional network) is appealing.
  • There are unlimited learning opportunities.  I get bored, and I really thrive when learning new things.  In addition to getting a CFP certification, there are all sorts of other niches (e.g. trusts and estates, crossborder taxation, etc.) that I could get education in.  None of these are particularly expensive, and they would all directly raise both my utility and my hourly rate.
Much to my surprise, I've already lined up a part-time paraplanner role.  I hadn't even started job hunting, but someone saw a post I'd made on a professional forum and reached out.  I really echo what @Metalcat said upthread about the value of the other skills we bring to these second acts.  I've been a BA for many years, and thus have a lot of useful IT and admin skills.  Before that, I was a teacher for over a decade, so I also have a lot of useful communication and presentation skills.  There's so much that I'm able to offer from day one as a novice paraplanner that other folks just starting out aren't able to do.

I'm excited to try this new path.  Based on my experience in the coursework and doing pro-bono advising, I feel like it's a great fit.  It ticks many of my boxes: helping people, feeling useful, solving problems, feeling valued, developing expertise, etc.  And, as others have said, I can always switch gears again in the future.

As far as whether or not I should have done it sooner, I don't have a strong opinion.  The time is right now.  I suppose I could have done it a year or two sooner, but having my income for those years was also good.  And I probably could have waited a few years, but I'm also glad that I'm not.

LadyLJCO

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Re: Who's had a successful Second Act careerwise?
« Reply #34 on: April 07, 2025, 08:55:47 PM »
I’m on the opposite side: 45 yr old library services professional contemplating law school. There’s a part-time program an hour away at a respected school so I could continue to work while in school. I have sat in on a few classes and find it very interesting. Goals would be mediation or law librarian or estate planning. I’m dying of bored-out in my current role but could sit tight and coast …but feels like a waste. YOLO and I like a challenge.

wick

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Re: Who's had a successful Second Act careerwise?
« Reply #35 on: April 15, 2025, 10:05:58 AM »
Dude I’ll be frank, I currently work in education and it exhausting and the money is really not great day in day out. I have a pension, which is great but I’ve got to work for 30 years to get the full benefits. I’m on the younger side so the time is not an issue but if I’m being frank I spend a lot of time wishing I’d gone to law school and was making more money. From a career educator I would say look for something else

formerlydivorcedmom

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Re: Who's had a successful Second Act careerwise?
« Reply #36 on: April 15, 2025, 10:50:34 AM »
I worked in IT for more than 20 years, and quit when we hit $1 million in investments.  I was in my early 40s.  I subbed for a school year, realized I liked it, and got my teaching certification.  It was a 50% pay cut for me, but we are able to live on our salaries and we don't feel the need to invest anymore.  Our money will grow itself.

I'm currently a third-year HS Economics teacher.  I LOVE IT.  The first year was so hard.  So, so hard.  There was no curriculum for me to follow so I had to make most of it myself, and obviously I wasn't great at it yet.  The second year was way easier, with more work-life balance, and the third year is amazing.  I have 3 teens at home, and I feel like I use my "mom" skills a lot at school.  it helps also that my personal kids are fairly self-sufficient.

My husband became a teacher at the same time I did.  He quit halfway through this year and is going back to his last (lower-paying) career.  He taught junior high in a school without a lot of administrative support.  He was working 80 hour weeks and was drowning. 

We will need to work a few extra years, since we stopped putting new money in the investment accounts.  I'm okay with that.

If you're going to try it, give yourself a timeframe.  I knew that my IT skills would still be up-to-date for 2 years.  That gave me 2 years to decide if this is what I actually wanted to do or if I wanted to go back to my old career.

Metalcat

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Re: Who's had a successful Second Act careerwise?
« Reply #37 on: April 15, 2025, 11:04:47 AM »
Dude I’ll be frank, I currently work in education and it exhausting and the money is really not great day in day out. I have a pension, which is great but I’ve got to work for 30 years to get the full benefits. I’m on the younger side so the time is not an issue but if I’m being frank I spend a lot of time wishing I’d gone to law school and was making more money. From a career educator I would say look for something else

I'm a therapist and the vast, overwhelming majority of my colleagues are former teachers.

Hula Hoop

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Re: Who's had a successful Second Act careerwise?
« Reply #38 on: April 15, 2025, 11:18:05 AM »
I work in a conventional office job currently but I'm training to be an ADHD coach.  I'm really hoping that I'm able to make that my FT freelance job at some point in the future and quit the office job.  For now, though, once I'm done with training I'm going to do coaching on the side in the evenings and weekends to try to get certified.  I still need the money I get from my office job as I'm currently the only breadwinner.  But I expect that to change at some point in future.

I know myself pretty well and this may or may not just be an ADHD thing (I was diagnosed about 3 years ago) but I find it impossible to just relax and not be busy.  I need structure to my day and new things quite often.  But I also hate being tied down to a routine.  I know I could do that with hobbies but coaching is really interesting to me and it will also bring in some income. The great thing about ADHD coaching is that it will be freelance so I'll be able to control my own time.  Also it will mostly be online so I would be able to travel and do it while away from home.  I'm really sick of being tied to my 9-5 office job.
« Last Edit: April 15, 2025, 11:19:51 AM by Hula Hoop »

classicrando

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Re: Who's had a successful Second Act careerwise?
« Reply #39 on: April 16, 2025, 06:28:04 AM »
I wish I could offer advice, but I feel like I'd need to have had a successful First Act to begin with. ;P

Nick_Miller

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Re: Who's had a successful Second Act careerwise?
« Reply #40 on: April 16, 2025, 07:25:42 PM »
So many interesting replies! I've enjoyed reading them.

I've thought about which do I fear most: 1) feeling unfulfilled or 2) feeling trapped, and I think I'm more scared of feeling trapped just because that has wider repercussions. For now, I'll try to enjoy my relative freedom and focus on that. Being able to take a walk whenever I want to at work, or take a long lunch, come in late or leave early, take personal calls, or just put my feet up on my desk and close my eyes for 5 minutes...those are things I shouldn't overlook or minimize, and they certainly aren't things I could do at a school-based job.

Maybe I will get buff and get into the fitness industry with older clients. Yeah that will happen.

ares99

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Re: Who's had a successful Second Act careerwise?
« Reply #41 on: April 17, 2025, 06:31:19 PM »
My current personal trainer is 65. I'm 52. I've done personal training in the past mostly with guys in their early 20's. I find that having an older trainer who understands the difficulties and limitations that come with aging to be a real plus. Best trainer I've ever had and I'm in the best shape I've been in for the the past 20 years. Also, it's is a second career for him. He was an engineer who retired in his late 50's. Seems to really enjoy doing the PT now.

ebella

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Re: Who's had a successful Second Act careerwise?
« Reply #42 on: April 18, 2025, 03:50:07 PM »
I'm in the same boat as OP.  Almoast 40 government attorney (just took the fork because was pretty sure I'd get riffed or put on Sched F so this was more money) and, honestly, my legal career has been unrewarding.  After 10 years I've only managed to pay off my student debt and squirrel away $500,000 in investments/retirement/savings which is all about to get obliterated in the stock and bond mkts volatility caused by the current administration.  We live modestly and I am looking at jobs now but the only ones I'm getting interviews for (no offers yet) would be a 30-40% paycut. I'd love to try something new, especially if I can do it in another country where I have family (alas, I do not have legal residency anywehre besides US).  But I'm at a loss. Law is so location specific (licenses) and AI is coming for it.  But, frankly, I'm too old to do manual labor and going back to school after I finally paid off my debts, seems like a lost cause. All this to say, I don't have answers but am curious what people did that did not involve more training/licensure/debt and actually helped them maintain financial goals.

Embok

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Re: Who's had a successful Second Act careerwise?
« Reply #43 on: May 13, 2025, 11:30:26 PM »
I spent 21 years in Big Law firms, founding two commercial real estate practice groups in Los Angeles as a partner, but got burned out due to the stress caused by the endless sexism and politics in that world.

I still like law, though, just not the firm politics, so 13 years ago I started a tiny law firm with another partner, focussing on commercial real estate transactions, financings, leases, and in downturns, foreclosures and workouts.

We don’t make as much money, but we work mostly from our home offices, take on deals we like and can turn down deals with jackasses, and can take time away if we want.  We don’t have to fight to do rational business development with firm money. 

The administrative overhead is a pain, though.  I have to do my own billing and filing.  And I would prefer to make more money some days.  I have to work pretty hard when a deal heats up though, as I have little support.

However, as I start to scale back to get ready to retire in a couple years, I can get outdoors for a walk, or have a cup of coffee during the day, or spend a month in another country while working part of the time, and that can be pretty sweet.  And no one can ever vote on me again.

There are definitely tradeoffs but we get approached at least once or twice a year and my law partner and I have not yet received any indication that there’s another law firm that we’d like better than our own, warts and all.

iris lily

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Re: Who's had a successful Second Act careerwise?
« Reply #44 on: May 14, 2025, 05:37:13 AM »
My husband started his own handyman/light carpentry business after having neighbors beg him to work on their houses. We lived in a neighborhood of oldVictorian houses and few owners knew anything about fixing them.,They meed constant repair.

He had an advanced degree in horticulture and was working for a tree company.

Anyway, on a Friday he left the tree company job and the next Monday started work oan a neighbor’s houseand was booked solid for two decades.He never advertised, his business came by word of mouth. He was the crown molding king of our neighborhood, putting  in crown molding in over a dozen houses. He never made a ton of money but he liked his job and had conteol,over his own time. He is very self motivated, and even in retirement at age 70 he works hard.

PacificaFog

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Re: Who's had a successful Second Act careerwise?
« Reply #45 on: May 19, 2025, 10:49:03 AM »
Love this thread as it is exactly where I am right now!  I’m in my early 50s and left my corporate job last year completely and totally fried. I’m still working on convincing my DH to pull the plug, hopefully in the next year.  Although we are probably at a point where we could lean-FIRE, I am thinking about options where I could work part time in a much less stressful job to bridge the years until we each get a small pension (7-8 years from now) - more of a coast-FIRE.

To that end, I have done some exploring this year. I just completed a 6 month life coaching course and I also volunteered teaching a course on job readiness at a local college this past semester. Like the OP, I am considering getting certified as a personal trainer (I think there’s a HUGE need for older, more mature trainers for all of the people in midlife newly getting into fitness). I am hoping to have a career that is some combination of career counseling, life coaching and personal training - who knows, maybe I’ll even throw in some outdoor rec since I did a lot of that in my 20s.

None of these things will pay anything close to my corporate job, but it sounds FUN and fulfilling, which certainly wasn’t the case for the past 10 years.  I also really only need to make enough to cover our healthcare and travel expenses. We have enough saved for daily expenses.

I’m optimistic and excited to see where it all goes, and so grateful to this community for putting me in a financial situation where this is even an option!

sonofsven

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Re: Who's had a successful Second Act careerwise?
« Reply #46 on: May 19, 2025, 12:06:10 PM »
I've been kicking around the idea of becoming a fishing guide.
On the one hand, I'm afraid it could ruin an activity I love dearly.
On the other hand I could buy a really nice boat; and it and all my gear would be tax deductible.

rklsoptmst

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Re: Who's had a successful Second Act careerwise?
« Reply #47 on: May 19, 2025, 01:11:12 PM »
Also 50ish --
 
My “careers”, are all entrepreneurial, with a through line of real estate. In my 20’s as a young mom, I bought a farmhouse with a large attached barn on a main tourist road in New England. Divided the front farmhouse into two apartments to cover the mortgage and building expenses and started selling antiques out of the barn. I slowly grew that barn shop into an upscale home and garden shop- adding structure, insulation, windows, etc. Once I paid off this building in full we turned the shop into a barn apartment and moved into it.

Meanwhile, My husband and I continued to buy and live in fixer-uppers, rent (short, medium, and ling term) doing it again and again...paying off the mortgages as could.

Starting in 2020 we sold off three properties every two years and now live in the original barn apartment, and the rentals cover expenses plus some.

Based on experience, my skillset includes: retail, marketing, running rental businesses, hospitality, carpentry, plumbing, design, photography, and probably a bunch of things I’m not remembering.

After few years fully FIRE’d, I am toying with a plan to get back into the hustle, since it scratches so many itches- socially, creatively, intellectually, and the thrill of newness trying different places to live.

Very likely it will involve some form of real estate, since that’s what I know. The landscape of real estate and the economic drivers are changing so quickly, and I like to get in on a curve before it peaks, I am trying to stay curious and open to where there is a need. Leaning toward some kind of “experience” based short/mid term rental in a place I’d like to sample myself! 

 

ebella

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Re: Who's had a successful Second Act careerwise?
« Reply #48 on: June 03, 2025, 06:59:18 AM »
I spent 21 years in Big Law firms, founding two commercial real estate practice groups in Los Angeles as a partner, but got burned out due to the stress caused by the endless sexism and politics in that world.

I still like law, though, just not the firm politics, so 13 years ago I started a tiny law firm with another partner, focussing on commercial real estate transactions, financings, leases, and in downturns, foreclosures and workouts.

We don’t make as much money, but we work mostly from our home offices, take on deals we like and can turn down deals with jackasses, and can take time away if we want.  We don’t have to fight to do rational business development with firm money. 

The administrative overhead is a pain, though.  I have to do my own billing and filing.  And I would prefer to make more money some days.  I have to work pretty hard when a deal heats up though, as I have little support.

However, as I start to scale back to get ready to retire in a couple years, I can get outdoors for a walk, or have a cup of coffee during the day, or spend a month in another country while working part of the time, and that can be pretty sweet.  And no one can ever vote on me again.

There are definitely tradeoffs but we get approached at least once or twice a year and my law partner and I have not yet received any indication that there’s another law firm that we’d like better than our own, warts and all.

I'm considering starting my own firm from real estate lit side. Mind if I pm you for advice?

Chris Pascale

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Re: Who's had a successful Second Act careerwise?
« Reply #49 on: June 06, 2025, 12:46:18 PM »
I went back to school in my 40s, fully retrained as a therapist, and launched my own practice in September.

Hope it's going great because from the posts you've put up on here I would guess you are very good, and people are happy to see you.