Entrepreneurship just leaves me exhausted

Today is one of those days where entrepreneurship is so hard, I start looking at job postings. For anything. Just something with health insurance that doesn’t leave me consistently stressed.

I left my job and decided to work part-time while I tried out my own business 10 months ago today. In the intervening months, I’ve launched a weekly podcast, created and launched a course, dressed up like Bowie often, wrote a business plan, landed a business grant, rebranded, made hundred of sales calls, give over 30 talks, was runner-up in a pitch competition, taught hundreds of folks about personal finance, and took my first and second paychecks from my business. The business is profitable.

I took out no debt, I sold no equity. But the business still isn’t supporting me fully and I’m TIRED. I’m tired of juggling full-time on the business and part-time executive-level work in order to just pay my bills and save a little. I’ve had 4 + 5 jobs simultaneously for most of my adult life, but nothing as mentally taxing as trying to build a business – let alone my business and my day job’s business. I know how lucky I am to have no dependents and a low cost of living and have had a decent paying job the past couple years that let me build up 18 months of savings to fall back on, but real talk: entrepreneurship is way harder than even the most physical blue collar and nonprofit jobs I’ve experienced. The usual mental stress around money is compounded by the stress of constantly creating something and making decisions.

But when you’re a small business owner, you always have to be optimist. You always have to say “I am on an upward trajectory, business is great, this business will succeed even though 95% of them fail!”

And some days I really, really feel like that. The highs of business are so high, but the lows are quite low.A bicyclist tries to bike in a straight line, instead it shows a convoluted path
I made lifestyle changes (quit all alcohol for example) to get my expenses below $1100 per month (a quarter of that is health insurance) so that I could start the business while working part-time without eating into my savings. I went from saving 52% of my income last year on the Portland median salary to occasionally dipping into my savings on a few months. I’m trying to practice what I preach with Oh My Dollar! but I genuinely miss that regular paycheck. A lot of this was more fun when it was a side gig.

I’m finishing up the 2nd draft of the Oh My Dollar! workbook right now, ready to hand off to the fabulous illustrator. It’s nearly there. But it’s hard. Making things is so hard. Especially when you’re trying to do it to feed yourself. It’s so much harder than writing grants and making budgets and analyzing data and the sundries of my white-collar career.

I have read a lot of business books and memoirs, and I keep wondering what part of the journey I am in now. Am I about to flare out and start eating into all my savings before ending up in a ditch somewhere? Or is this the chapter where I grind a bit more and then the tide turns and I’m on a rocket ship to the top (mixed metaphors much)?

Right now, that graveyard shift at a convenience store I used to work is looking pretty attractive. 

79 thoughts on “Entrepreneurship just leaves me exhausted

  1. Hang in there and know that all of us who are entrepreneurs are having the same struggles. Ups and downs, sleepless nights, shoes dropping and sudden victories are all part of the territory. Somehow we find it’s worth it. The creative opportunities and flexibility are a big perk. You get to choose when, where and how to do the 18 hours you work each day and who to work them with.

  2. I know enough about the grant cycles + education budgets in high school ed to want to avoid that ;) I am working on some after-school program modules for clients for that age group though. Just so many plates to spin!
    (regarding an easier customer service job, I’ve definitely thought about it. I did grocery for 5 years. I’m also bartender trained/OLCC certified and there’s some barback gigs being listed. Bars are great for personal finance.) In reality, I have enough personal cushion that if I was willing to take a leap, I could get this book out without taking on another job to pay the bills.

  3. Maybe Starbucks or New Seasons. Part time = benefits and you can talk with the public about finances! Great job this year. Inspiring work. Don’t get too down these things take time in addition to hard/quality work. Idea: tailor to high school students and get districts to buy it.

  4. There are a lot of resources for entrepreneurs in this town. I know that I would have quit so many times if I didn’t have someone there to check in with me (and hold me accountable for things) and have a community that I feel supported and inspired by.

  5. Real talk: this whole business might have to go back to being a side project and I might need to get a MegaCorp job if Trumpcare passes because I am NOT insurable with pre-existing conditions not being covered and/or having extra premiums (my premium might jump to $3000 per month based on recent estimates).

  6. We’ll see what happens with TrumpCare. This self-sustaining business goal is all for moot if they start being able to adjust premiums based on risk. I can’t afford a high-risk pool; my medication is $3,000 per month (!)
    At least your little one will be out before they can make any changes!

  7. I know in theory nothing will likely change until end of 2018 as far as my coverage, just based on the way things are going. And hopefully/theoretically/based on projections, I can get this business to supporting me before the end of the year. So I’ll have some lead time to figure out if I need to find a MegaCorp or gov’t job. I luckily have low expenses, so as long as we don’t enter another recession, even a customer service minimum wage megacorp job with health insurance will cover my expenses + some savings.
    I SHOULD be buying myself some time, with the amount of runway I have (>18 months of expenses, including health care, in savings).

  8. FWIW, my version of your struggle is exactly what *15 years ago* drove me to get a p/t job in retail that I needed to become a f/t job in order to stop paying $1000/month for health insurance. It took me almost 30 years to finally come to that decision and choice. It worked for almost 15 years, it but stopped working when I lost my last f/t job in 2014. Now I’m 62 and paying my own health insurance again and it’s due to go up by 30%+ next year. #UNSUSTAINABLE
    It’s better to come to where you are now at 30 than it is to come to it when you’re in your 60s. My advice is to get the best-paying job you can get that you can stand, w/the best health insurance you can get, until this all settles out one way or the other. You are young enough and hard-working enough to pick it up– even as an ex-pat, if it comes to having to leave the US– and make it work in a few years. But things are so up in the air now and you have real issues to deal with.
    One step forward, two steps back, three steps forward and onward until morning, I say.

  9. For a long time, it was one of the biggest factors in small nonprofits as well. So many talented EDs + staff having to leave because of the org not having/being able to get/able to afford health insurance and no individual plans available.
    I went without health insurance for so long, so so long I just CAN’T now. My medication is $3000 a month and actually fucking works. I’d hate to lose that.

  10. Affordable health care fuels innovation. Having volunteered in orgs that support entrepreneurship for several years, my experience is that the #1 block for potential entrepreneurs is lack of health insurance.

  11. Hey, I feel you. I can’t think of anything I’ve done that has been a straight road to where it ended up, and most of those have been failures on the larger scale. But the biggest thing I’ve seen separate the two is persistence: if you keep learning and being creative you will make it sustainable. Is there a way to turn the disaster of healthcare into an opportunity to help ppl? Personal finance and health b/c it can be truly life or death.

  12. I thought of you this morning. I really wish that I had learned the $$ skills that I learned in your class in HS or college. I still imagine there is a market out there for it. I also wish I’d learned damn strategic planning… and having to present leadership discussions with no training. Grrr. Don’t give up – what you teach is desperately needed by many!

  13. I love and appreciate the work you do and the way you share about how you make things work (by working your David-Bowie-tail off). You are a solar powered super star, but I also hope you move into a space where you are more supported by things other than your own force of will.

  14. I know those feels. Hang in there! I think you’re doing remarkably well for your first year. Took me several years before my business was truly profitable and sustainable. Close to 10 years in and I still ask myself “What am I doing with my life? Is this worth it?” every day.

  15. Not an entrepreneur, but I feel this 100%. There was a day where I laid on the floor of the office surrounded by chaos and felt like I was on the ‘ending up in a ditch’ trajectory. But I wasn’t. You’re not either, bc you’re a badass. If you need to step back to take care of yourself, that’s OK too – and if it turns back into a side gig so you can have health insurance in this fucked up society, that’s not failure on your part. Either way, I believe you’re on a rocket ship to the top.


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