The Honest Truth About My Biggest Failure (So Far!)

Have you ever had one of those times in life when you’re just on a roll? When everything seems to be going in your favor? Not that it’s all easy, but that it’s working – things are falling into place, and everything seems to be aligned.


Several years ago, I was flying high: I had started a small business that was growing successfully. I was winning awards and appearing in the newspaper. I felt important and respected. So important and respected, in fact, that another company approached me about acquiring us! Being asked to merge felt like a huge validation of our hard work, and as the leadership team sat down to discuss the potentially merger, we toasted ourselves and our success.


Within two months, we had made the decision to merge with the other company, and I moved our headquarters from my living room into their downtown offices. I traded in my daily yoga pants uniform for pencil skirts, and began my role at the new, larger organization.


I lasted there 9 months.


I had tears in my eyes as I handed in my letter of resignation. It was my shortest period of employment ever, made even more embarrassing by the fact that I was walking away from my own company, too, that was now a part of this larger company. A huge part of me didn’t want to do it, but I knew that I had to. I believed fully in the vision of the new organization, but it wasn’t a good match for me as an employee.


I had failed.


It was a failure not because the merger was a bad idea in the first place. The merger made sense. But in looking back, I realize I took the easy way out. I didn’t ask all the questions I should have. I got wooed by the money and the prestige. It’s not uncommon when one brand is larger and more established than the other: several months ago the merger between home technology companies Nest and Dropcam was revealed to have lots of uncomfortable tension that the two CEOs have gone on record saying they wish they had sorted out beforehand.


I take full responsibility for getting stars in my eyes about the promise of being acquired by a larger company. I didn’t do my due diligence, and I didn’t spend enough time thinking about what I was getting into. The good news is that the merger has paid off for several aspects of the organization I founded, and that was my first priority above everything else. But it wasn’t a great move for me, and I didn’t know it because I didn’t do my homework. It’s an embarrassing mistake for a founder to make.


No, I don’t regularly appear in the newspaper anymore, but when I handed in my resignation letter, I did take some time off to publish my first book. As with most things in life, the pendulum ends up swinging back and forth and evening things out in the long run. I do important work in different ways, now, and I’ve landed in places I might never have gotten.


So… have you ever had a failure that haunts you? What are your best ways for getting over it? I’d love some feedback for another blog post about picking yourself up and dusting yourself off after failure, so send me your stories!