I quit my job on Wall Street to start my own business

Hey Indie Hackers,

This is my first week as a full-time founder, as I recently quit my cushy finance job to start my own business!

If you're considering quitting your own job to go full-time on your side project, you may find my decision-making framework helpful.

Here's a breakdown detailing:

  1. Details about my previous job
  2. My thought process in deciding to quit

Let's get into it!

About the Job

  • Financial analyst and globally recognized bank
  • Rotational program feeding AVP (Associate Vice President) positions
  • $80K total comp: $70K base pay w/$10K signing/relocation bonus
  • Incredible, comprehensive benefits
  • First job out of college

Factors in Decision to Quit

  1. Passions
  2. Skillset
  3. Support
  4. Financials


I went to school for Hotel Administration - essentially a business degree through the lens of hospitality. I didn't know what I wanted to do, but I knew I wanted to serve others.

As I progressed through college, banking/consulting grew wildly popular with my peers.

I was in the top of my class, excelling in finance, accounting, and real estate classes.

Banks were trendy. They were socially accepted. They paid well and had great benefits. I was able to convince myself that financial analysis was something I enjoyed.

It's not.

I've spoken with representatives of various other disciplines within finance. It's not just the team I was on - no matter how hard I tried, I could not get excited about corporate finance. It just wasn't for me.

Meanwhile, I found myself thinking about my startup whenever I had the time. I thought about it in the shower. I thought about it before going to sleep at night. I started zoning out of meetings at work to think about it.

I started sneaking in work at my startup whenever I got the chance. People from around the world were reaching out to me, asking me when I was going to launch.

The more I thought about it, the more it became clear that corporate finance was not the place for me.


When I examined the skills I consider to be my "superpowers" - the ones I am exceptionally good at, the ones that set me apart from others - they didn't align with corporate finance.

These skills include:

  • Writing
  • Creativity
  • Visual Art/Design
  • Empathy

I realized that if I spent the next 5 years of my life creating financial projections, I would become exceedingly good at creating financial projections while becoming less good at other things.

I didn't want to lose my superpowers. That prospect terrified me.

Instead, I wanted to do something that would allow me to leverage my superpowers to the greatest extent possible. Doing so would allow me to create the most value.

And in my case, my superpowers did not align with the job I was in.


Coming from a background of excessive overachievement, I deeply wanted the support of my parents in order to feel good about this decision. I know how hard they worked to put me into a great school, and I recognized that they felt my finance job was successful and secure.

When I told them about my desire to quit my job in favor of working for myself, they were concerned.

As parents, they wanted me to be safe and to have a successful future. But they also wanted me to be able to reach my full potential.

When I explained that my skills were being underutilized, that I felt stifled, they understood that my job was not the best fit for me.

After I explained my thought process and my plans, they even offered to let me stay with them while I figured things out.

This was huge.


No matter how much you want to leave a job, you can't do so if you can't afford to live without your income.

I have around $30K total right now. Most of it is invested in stocks and crypto, but it's liquid enough to take out if needed.

But by leaving my job within a year from starting, I would need to return the $10K signing/relocation bonus I received.

This would leave me with $20K.


  • $157/mo for my student loan payment
  • $36/mo for various subscriptions
  • $57/mo for other expenses
  • $300/mo for food
  • $900/mo for rent

This would leave me with $1,450/mo of expenses, or $17,400/yr.

I wanted to give myself 1 full year to see if I could make it on my own. If I drained my bank account, I would still be left with $2,600.

It would be cutting it close, but I was resolved to make the investment in myself, to give myself and my startup a chance.

When my parents came in with the absolutely gift of letting me stay with them rent-free, it strengthened my resolve to take the leap.

Should You Quit Your Job?

Ultimately, no one can tell you how to live your life. But I'd recommend examining your own Passions, Skillset, Support, and Financials when making your decision.

And when it comes to deathbed regrets, very few people regret things they did. Most people regret things they didn't do.

And ultimately, life is too short to do something you don't love!

Thanks for Reading!

If you liked this post, follow me on Twitter!

If you want to hear a more complete rundown of what went into this decision (and a little motivation for you if you're on the fence about quitting your own job), you can check out my YouTube video!

  1. 3

    As someone who also left the world of finance for startups, good luck!

    1. 1

      Wow, but you're an extremely brave person. Especially because you risked abandoning everything and starting something new in your life. I had that decision a few years ago. It was extremely difficult, I even had to turn to factoring companies in Chicago because I did not have the capital to invest. Being an example both for young people and for every person who wants to be a successful man, I have read your history very carefully, it is really impressive. I think everyone should analyze your decisions and try to implement something in their career, maybe even a book to write so that the information is available to everyone

      1. 1

        Thank you so much for such a kind reply!

        As much as I'd love to take credit for the lessons I've learned along the way, the real credit comes from taking the time to listen/read and heed other's advice - so I'm happy that what I can share here is helpful/inspirational!

    2. 1

      Thank you so much! How is it going for you so far?

      1. 1


        It worked out well - I landed in HubSpot where I learned a ton about marketing SaaS and how SMBs operate/the challenges they have and I've put that to work in my own startup where I help SMBs build strategies to get found on Google.

  2. 2

    Hi Aprilynne,

    Where are you at in starting your own business?

    It didn't say in your YouTube video, other than some traction.

    I've heard of people quitting even when their business is already making money, and still they had to resort to looking for a job again when it became clear their revenue wouldn't cover their expenses in time.

    Growing a business from nothing to profitability is hard.

    Growing a business from nothing to profitability, within a set time frame, is even harder.

    That said, you should do what your heart tells you to. Obviously you've quit your job already, so done is done.

    But this is coming from a guy who quit his job in 2019 when I had a product and tried to sell it full-time, and then having to look for a job yet again when it was obvious it didn't work. I was halfway through my runway, and I knew there was no way this was taking off the way I thought it would, and I was right:


    Either way, I do wish you the best, but I think it's important to share the other side of the story. This will probably be the hardest thing you've ever done in your life in terms of your career, but you made a really good point about wanting to explore your potentials to the fullest instead of just coasting on a job.

    My personal opinion is that it's rarely necessary or even helpful to suddenly cut off our only source of income when trying to start a business. Trading an infinite runway for a limited runway is not really a good idea. There's ton of research that shows that anxiety that results from poverty can reduce your IQ by 2 standard deviations, so if you're worried about money all the time, you're not going to be able to start and grow a business at your best anyway.

    Of course having supportive parents help a lot. I think they're just naturally concerned that, if you fail, you'll burden them instead. But I think if you share with them what you're doing, and the progress you're making, it'll make them even more supportive of you than they already are.

    $20k (after the $10k penalty for leaving early), and that even includes volatile investments like crypto, sound a bit inadequate to me, though. It could be the best decision of your life, or it could a scary ride ahead.

    I really hope you prove me wrong. I think you'll prove me wrong.

    Keep us updated and good luck!

    1. 1


      Appreciate your opinion!

      We're pre-MVP, but post-revenue (made a little over $300 in the past 2 weeks through manual operations, and we're just getting started.)

      I'll say that regardless of what happens, my parents aren't afraid of me being a burden. I actually do have a number of job opportunities open to me right now.

      Ultimately, I realized that corporate finance wasn't for me. I had a couple of options:

      • Stick it out for a few more years to complete the rotational program
      • Leave and join a startup
      • Leave and go full-time on my own startup, give myself a year to see how it goes, and then join a startup at the end of the year if needed

      The third option seemed more fun to me. And if I didn't go full time on Tenderfoot, but someone else made a Tenderfoot replicate and succeeded, I'd never forgive myself for not having the courage to take a chance and give it its best shot at succeeding.

      To me, the opposite of success is not failure. The opposite of success is stagnation. And I felt that if I stayed any longer in finance, my skills would stagnate.

      And keep in mind I've been working on Tenderfoot on the side since March, so it's not like I'm jumping into a brand new idea! I've let it be a side project for as long as I could before feeling like it needed to be more.

      There's a lot of other factors that went into this decision that I couldn't really include in the post/video without it being too long, but happy to discuss further!

      Additionally, I have a few other sources of revenue right now (including Twitter banner design - super niche but making surprising money) that I'm considering building out as well.

  3. 2

    So you quit your job and moved back in with your parents because you didn't emotionally enjoy your job and wanted to work on this other thing that you felt would emotionally get you excited about work? Look I'm not downplaying the bad over the good here but I'd recommend you go work for another startup that's paying you and see for yourself how crazy that world actually is before you ask your parents to essentially pay your rent while you find yourself in the startup space. I'm not saying don't do it but try working for a startup first to see both worlds.

    1. 2

      Oh I have! I worked for a Series A VC-backed Startup for a year. I came in as an intern as the 13th employee, worked 70-hour weeks when my "manager" left the company and I was promoted to her role, was constantly putting fires out, never had time off, and I loved pretty much every second of it.

      And then I tried out corporate finance and I realized that once a maker, always a maker. Finance really just wasn't for me.

  4. 2

    Cool story, good luck to you Aprilynne!

    1. 1

      Thank you so much! I really appreciate it!

  5. 2

    Best of luck, love that you are not just holding Fiat but invested in stocks to Crypto to make some gain.

    It's a nice idea to grow the money which you already have

    1. 1

      Thanks! Absolutely - diversified investments are key!

  6. 2

    i’m sure some will disagree with this but you can probably just keep the signing bonus. if they tell you to pay it back but don’t give you a formal way to pay back less the taxes they took out and with it done in such a way that the payroll software they use will account for the claw back on your w-2, giving back the money will screw you over more than not having gotten it in the first place.

    1. 1

      Hm I'll see what they tell me to do. There will likely be formal process, but not doing anything until they tell me to.

      Definitely not looking forward to returning a full $10K when I only received $7K of it post-tax. Will hopefully get most of it back during my tax return, though

  7. 2

    Congrats on taking the first steps towards being an indie hacker! I'm sure you will do just fine after reading your post!

    1. 1

      Thank you so much! Seriously love the indie hacker community, and I'm excited for what's in store

      1. 1

        If it helps, I can offer you a free access to GrowthHunt.co, a database of business strategies that I've curated and summarised to help get you started.


  8. 1

    Having done something similar in my life ( and maybe even more risky than your personal version) I can't tell you that it definitely aids in laser-like focus. With the calendar running like a stop watch you have to harness the time, the fear, the focus, and tight planning to "break through" to the other side where you are able to support yourself again and hopefully go UP from there. If at any point you start getting mentally rough around the edges take a day off, the loss in productivity will allow for greater productivity over the long haul. Try doing everything as a series of small steps to avoid mental overload and to see progress for yourself.

  9. 1

    Congrats. Wish you all the best in your next step!

    1. 1

      Thank you so, so much!

  10. 1

    Great read. Wish you all the best!!

    1. 1

      Thank you! I'm glad you enjoyed it!

  11. 1

    Congrats for the big step and good luck!

    1. 1

      Thanks so much! Excited for what's ahead

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