Need some advice please!

[bobthefrog]

Hi everyone!

I'm at a place in life where I know I'm ahead of the curve, but I know I can't have it all and I don't want to make bad decisions that undo my gains. I'm hoping someone with more wisdom than myself can mentor me a bit. My job is driving me insane, I loathe working on salary and being expected to be present whether or not I'm being productive. I feel like I'm in prison all day. *But* it pays well, and I'm making good financial progress. My serious girlfriend just quit her job to go to school for nursing. She'll be done in ~3 years. I have promised to provide her ~$700/month for her to live on.

Here's my financials:

Age: 28
Current income: 115K before taxes. Currently saving between $2k - $4k/month
Housing: $150K condo, mortgage is paid off, ~$300/mo expenses -- utilities, HOA, etc
Retirement savings: $28K 401(k), $7k Roth IRA
Cash savings: $14k
$10k car, paid off
$5k motorcycle, paid off
Somewhat inaccessible inheritance in stock fund: $130k (difficult to access, would have to have a very good reason)
Education/experience: masters degree in computer science, 5+ years experience in software development

My goals: I want to work 20-30 hours a week on a business of my own or at least on something that is meaningful to me. I want to provide a good financial safety net for my girlfriend (future wife) and for the possibility of having kids within 5 years. I want a small plot of land to grow my own food and the time to do it.

I have been wanting to work on creating a business on the side, but I get so burnt out from work that I can't find the motivation for it. I feel like to get any momentum on that goal, I need to make it my primary focus.

Basically, I'm frightened of giving up the high-paying job because it will turn my cash flow negative and I will face criticism from family. It seems like a clearly bad financial decision. It also seems like bad timing with my girlfriend just starting nursing school.

On the flip side, my startup job is stressful enough that it is badly affecting my health and my very good relationship and it is preventing me from doing many things that are important to me. If I were single I think I would temporarily move to a country with low cost of living and offset my expenses with the rental income from my condo while I proved business viability.

I'm feeling a bit stuck (the irony of being "stuck" in a relatively good situation is not lost on me). If I stay on the career treadmill for another 10-15 years, I think I could easily become completely financially independent. If I jump off, I am afraid about my ability to re-join the workforce if I realize it was a bad decision.

Can anyone give me some advice? I'm just feeling a little lost and need some guidance. Thank you so much!

[gooki]

Have you considered changing to a less stressful part time job so you can do both (bring in an income, and work on a side business).

[davisgang90]

If you are passionate about your side gig, have you considered asking your boss to work fewer days a week?  Are there opportunities for telecommuting?  If you are valued, your boss may be willing to work with you.

If those aren't options, I would start looking for a company more in line with your goals.  It sounds like you have some very marketable skills, a smart employer would work with you to retain them.

Good Luck!

[aj_yooper]

I am sorry that you are feeling unwell now, but you have done very well in your life so far-degree, excellent income, girlfriend, goals.  Since your health and personal relationship are being affected, I would have a good conversation with my physician and girlfriend to find ways to minimize issues and get started on a plan.  You are a capable person and will be able to solve this, but it will take some time.

Best wishes.

[MrsPete]

Your girlfriend is just about to embark upon an educational endeavor, and you've promised to help her.  The two of you will both benefit from her finishing this degree.  I'd say this is not the time for you to take a financial risk too.  One person at a time.  Three years isn't all that long a period of time.

I know that when I have to do something unpleasant, it is easier if I know the task has an end-date.  You could say that you need to stay in your high-paying job for now . . . but your end date is her graduation date.  That can also serve as your start date for your part-time, self-employed gig.  Between now and then, you can put some time into how it might go, but get serious about it once she's out of school and has begun working.   

Your living expenses look low.  I'd focus on maintaining them at this level. 

[bobthefrog]

Thank you everyone. It sounds like I wasn't too far off a good solution -- I applied for and nearly landed a part time telecommuting gig that would have been a big pay cut but would still have paid the bills fine.

My girlfriend is worried about me and has expressed willingness to do anything from moving to taking out student loans to quitting school and moving abroad. It seems more clear now that I just need to find a less stressful way to keep money coming in and help her get through school without distracting her with my crap. Just gotta get back out there.