My Top 25 Lessons as a (Former) Entrepreneur


Five years ago, I decided to quit corporate America, and live my dream of opening up my own custom cake studio and becoming my own boss. It didn’t take me long to figure out that being an entrepreneur wasn’t so dreamy.

I faced a nearly year-long battle with architects, builders, and town officials just to get my studio built. I’d be lying to say that the end result wasn’t completely gratifying, but it was the waiting that was murderous. I spent so much time sitting around waiting that I began to wish that I had kept my corporate job longer. At least that way I would still have been bringing in some money and not just spending it while officially doing nothing.

Of course, I didn’t really do nothing. I found things to fill up my new-found free time. I taught myself about social media. I became a little obsessed with twitter. I investigated how to get my cakes published. I worked on my website. I knit. I discovered baseball. I watched a lot of documentaries. But mostly, I felt like I was going completely insane with impatience. In retrospect, I’m beginning to think that my very reason for this lifetime on earth is to learn patience. You’ll see it’s a more than common recurring theme in my life if you stick with me. Yes, I’m now asking you to be patient. 🙂

I don’t care how many books you read, or how many courses on entrepreneurship you take, nothing will prepare you for endless months of battling hurdles while watching your once hefty bank account dwindle to $0 quicker than you ever imagined. I had fluttering thoughts of,  “Are you really sure you want to do this? Is this the right choice? Are you really good enough?” flying through my brain ALL the time.

And then, after months and months and months of waiting – my studio was done. It was a blank slate. I was officially “Open for Business”. Woo hoo! Bring on the overnight success – just like “all those people on tv” right? Um, no.

It wasn’t all a “piece of cake” (I hope to god I don’t hear that expression again for a long, long, long time.) Lots of great things followed, and of course, some tough life lessons too. Entrepreneurship will expose parts of you that you never knew existed. And, as with many things, exposure leads to strengthening. I definitely toughened up in many aspects. Unlike in my corporate life, where I had to sell myself on job interviews and new clients, as a business owner, I had to sell myself with every client, with every social post, every day . As a natural introvert, with a tendency towards self-deprecation, this was not easy.

There were a lot of things that I learned in five years of my own, self-guided real-life class of entrepreneurship in the world of cake. So while I embark on this next phase of things to come, I thought I’d start out this new blog with my top 25 lessons learned. I have a feeling that some of them may come in handy in the future … whether you are an entrepreneur or not.

  1. No problem is insurmountable.
  2. There is a very small list of people that you can really depend on.
  3. The IRS is a bully.
  4. The squeaky wheel DOES get noticed. You just have to master the frequency of when to squeak for the best attention.
  5. If you always say “Yes” to media requests, you’ll get more.
  6. Saying yes and figuring out how to actually get things done after the fact is a sure way to increase your stress level, but it also forces you to learn and grow.
  7. Media darlings (i.e. those that the press is always publishing work from) do not necessarily have the most successful businesses.
  8. People who are not self-employed will always think that “living your dream” as an entrepreneur is dreamy and will be jealous of you.
  9. You will be jealous of those with a steady paycheck, and even more so those people who possess that dreamy thing called “an expense account”.
  10. You will work odd hours, and not be able to socialize like “normal” people, since you will be working nights and weekends.
  11. Your relationships will be tested.
  12. Not all relationships will survive.
  13. You will crave sleep, but know exactly how much sleep you need to effectively work. (I could work 48 hours straight, but any more … and I knew I shouldn’t be near any kind of knives, or slippery butter-stained floors.)
  14. You are probably your own worst critic.
  15. Sometimes simplicity IS best.
  16. Other times, over-the-top, “you have got to be crazy for even fathoming that” ideas are the ones that will become your trademark.
  17. You will hate yourself for comparing yourself to your peers, but you’ll get sucked into the facebook/twitter/website/blog post funnel at some point (“market research”) and will think that EVERYONE else has it all figured out and is super successful, and you are a a hack.
  18. You will quickly realize, after paying close attention, that social media is like any other business tool – where people showcase their shiny, and hide their blemishes.
  19. You will have your morals tested. Whether you let the almighty $ win is up to you.
  20. There are some amazing, wonderful, easy-to-work with, and appreciative clients out there. (This may be the brightest memory of entrepreneurship for me.)
  21. There are some clients that will challenge you to the nth degree – these will teach you the hard lessons – When to say no. When to stick up for yourself. When to back down. When to never accept payment upon delivery again. I could go on and on and on …
  22. Everyone in this Pinterest-obsessed world will want amazing, super-elaborate, “perfect” cakes, but the majority (i.e. 99.9%) of them don’t have the budget for something even half as nice as their “dream cake”. [For you cakers: The classic fondant and gumpaste laced-dreamer clients with less than buttercream budgets.]
  23. All those people/businesses/events that want something for free in exchange for “publicity” of your business – do NOT fall victim for this. Is your business worth nothing? Do NOT work for free.
  24. It’s a rough world out there. In the NYC metro, it IS cutthroat a lot of the time. As hard as it is, try to make friends in the industry. In your niche is ideal – but even within the larger spectrum is great. Some of my best clients came from referrals from other wedding industry friends I made over the years.
  25. Know when to walk away. (Still a lesson in progress …)

About Jen

Wife, cat-mom, and new Brooklynite. Collector of cookbooks, typewriters, yarn, and all things shiny. Pro-baker & food lover readjusting to office life at JBF.
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