Wild Problems

It feels like years since I quit my cushy banking job and leapt into entrepreneurship. The freedom is wonderful, but I’d be lying if I said it was all rainbows and unicorns; this sh*t is hard. Exhilarating, but still hard. Here are some of the biggest pros and cons of leaving the corporate world.

  • Pro: Total autonomy. I can do what I want, when I want, from where I want. I’m no longer chained to my desk.

  • Con: Sometimes I miss having a list of tasks that need to get done that day or that week. When there’s external accountability, you don’t have to rely so much on internal motivation.

  • Pro: That feeling when someone recognizes your value and trusts you enough to sign on as a client - and part with some of their hard-earned money.

  • Con: No more steady paychecks. No more yearly bonus. No more stock options.

  • Pro: The first half of my career was in the Big 4 where very little time is wasted. Then I “went corporate” and suddenly understood all the gripes about useless meetings. For years I suffered through mind-numbing conference calls. That is now over.

  • Con: I feel like I need to operate at 100% efficiency 100% of the time. There are no breaks. I can’t fold my laundry during a meeting. I can’t listen to music while doing mindless work. I have to always be “on”.

  • Pro: I don’t have a boss.

  • Con: I don’t have anyone to pass off busywork to.

  • Pro: I am approximately 10,000% more creative now. I make every single decision on within my firm, from the website’s color scheme to mutual fund selection. I get to write and design and ideate and make nerdy Instagram videos.

  • Con: I have so many ideas there’s no chance I’ll get to even half of them. And I’m always thinking of new ones, plus a million to-do’s, reminders, updates, edits, etc. My mind is racing 24/7 and I’ve noticed I keep forgetting little things, like my keys or what I meant to grab in the garage. It’s weird.

  • Pro: I’m no longer working for the weekend. Every day (even Saturday and Sunday) is a day to build, to get better.

  • Con: My internal clock is out of whack. It’s tough to remember what day of the week it is. The main thing keeping me on schedule is my family. #humblebrag

If you are an aspiring business owner sick of the 9-to-5 grind, the decision to leave or not is what Russ Roberts calls a “wild problem.” Like getting married and having kids, there’s no way to know if it’s right for you until you try it out. So if you have the urge, I say do it! Just make sure you have a backup plan.


Devin Faddoul, CFP® is the founder of Adda Financial | Outsource your financial life. Focus on your real life.

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