Author Topic: What to do...  (Read 2125 times)


  • 5 O'Clock Shadow
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What to do...
« on: March 17, 2018, 06:22:35 PM »
Hi all,

I hope this is the right area to post, but I'm basically just looking for advice on how to move forward. As a background, I started working when I was 17 and became very good in the field of IT. I did that for 9 years and then moved into more of a technical sales capacity. I'm 27 now, with a rental property and about 500k net worth. My salary is 200k (with great potential historically to overachieve).

I suppose life is good: great gf, dog, nice apartment, travel a few times a year, job is really rewarding and enjoyable + I work from home. I save a significant amount of my take home pay (max 401k, rollover IRA, max HSA, rental property pays for itself, max employer ESPP, thousands going into index funds/robinhood/wealthfront and no debt besides the house).

However, I have this real urge to start my own company or do 'something' bigger. The problem is now that I feel so secure with my current lifestyle, I have a hard time taking the risk. Additionally, even if I wanted to start I don't really know what business I'd want to start.

I guess I'm here to see if anyone has had similar experiences in life and what you did? My current life feels like it will be 'safe' if I keep investing, likely work towards management in another 5-7 years or so and then retire by 40 at this rate. I get bored easily so I doubt I will ever really retire, but at least retire from the normal 9-5.

Feedback & questions welcomed.



  • Handlebar Stache
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Re: What to do...
« Reply #1 on: March 17, 2018, 06:35:37 PM »
Starting and running a company involves a whole lot of bullshit largely unrelated to gizmo/service offered by the company. There's a good reason why many founders hire in a CEO.

If you have the itch to start a company of your own, I'd suggest A) spend some $$$ and have an attorney read over your employment agreement with your current company, and B) start your company as a side hustle until its cash flow positive. Things often take twice as long and cost twice as much as you expect.


  • 5 O'Clock Shadow
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Re: What to do...
« Reply #2 on: March 18, 2018, 05:46:22 AM »
Good idea - I like the idea of a side job. I suppose now its all about coming up with an idea that Im passionate about.


  • Stubble
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Re: What to do...
« Reply #3 on: March 18, 2018, 06:39:06 PM »
IT guy here as well. I'm considering doing some side gigs on some of the freelance sites. I'm not looking to start a MSP, software company, or consultation firm. I'm just looking to make some extra cash to invest. The post about the BS is spot on. Where I live, even a blog with a few ads requires a home business zoning permit, business license, and property taxes on everything used for it. Then there is the extra tax paperwork at the state and federal level. If I'm going to jump through enough hoops to be mistaken for a 1 man circus, I'm going to make it worthwhile.


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Re: What to do...
« Reply #4 on: March 20, 2018, 02:41:30 AM »
Get a hobby and keep pumping the firehouse of cash. You’ve already won the game, there’s no reason to throw the dice again. What you need is way to find meaning other than from your job. That could be a side gig, volunteering or pro bono work, or a hobby you really connect with. All of those will stick around more easily when you do retire, and you don’t have to risk your ridiculous awesome salary and fast progress towards FI to do them.


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