Deciding When & How to Quit

First post on WSO but long time reader. I think this is the only place people will be able to relate to my situation so I wanted to share.

Background: 23, private wealth associate, $115K/year.

For context, I graduated college with ~$100K in debt and no money whatsoever. I felt like I had a (metaphorical) gun to my head. It's been 2 years and I've paid off $90K of that debt ($15K remaining) and I have around $210K in assets (so "net worth" right now is around $200K).

I realized early on that my corporate income (albeit 6 figures) was not enough. So I started an online business and made $100K+ profit in 12-15 months. I'm not saying this to brag, I just want people to understand my situation.

The last 2 years have absolutely been the worst of my life and my mental/physical health have severely declined (I imagine many here can relate...).

I currently live with my parents as a result of WFH, and my expenses are close to 0 (I literally own close to nothing; no car, etc.). I do pitch in around $3K a month to help them out, though (which feels good, but by no means obligatory).

Like many of you, my job is very demanding and even when I do have "free time" my energy feels totally drained. Now that my financial situation is better, I am seriously struggling to stay motivated working. Even if I "crush it" there, it feels like my upside is very limited and my quality of life will continue to suck.

I think I can probably clear $300-400K with the business I've built (and at the very, very least I can comfortably cover living expenses) - but of course there is risk in being an entrepreneur.

I already told my boss I was quitting and he asked me to take a long vacation and rethink it, and try to come up with ways the job could be more tolerable (I have substantial leverage...). Pushing for a salary increase doesn't really move the needle for me...quite frankly I am miserable and feel like I am trading my life/happiness for $6.5K/mo. (after tax). Additionally, my company will likely require a return to office in Q4 which I have already decided is a dealbreaker (so leaving is inevitable anyway).

Even though I am financially in a pretty good place and have a solid second source of income, it is still difficult to leave the job. Possibly "scarcity mindset" or just fear generally...I don't know.

It seems like an absolute no-brainer to leave - the potential upside is tremendous and the downside would be minimal. If I stay, the upside is minimal and the downside is tremendous (opportunity cost).

Is there ANY reason I shouldn't quit this month? I even talked to a "performance coach" that our company employs and she completely agreed with me.

Some friends have suggested "coasting" for as long as possible, but quite frankly that's not my personality. I also work in a client-facing role servicing HNW families and I'd feel like a piece of shit slacking off. Would rather lose the income than damage my reputation.

Curious what people think, at the very least this was helpful for me to put down in writing - thanks all.

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Comments (5)

Apr 2, 2021 - 2:37pm

Personally, I would ride it out another 2-3 months to pay off the remaining debt and then declare independence around July 4th. I think simply having the end in sight would be a huge relief. It sounds like you're on good terms with your boss. You might just approach him/her and figure out a 2-3 month exit plan which ensures continuity for the company and achieves your goal above. Congrats either way, you've done an incredible job and are in a good position.  

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