What it's actually like to look for a job as a "failed founder"
It's honestly different than I thought it would be-- in a good way.
I knew I had to get a job in October of last year. Simply put, the decision made itself: I needed money, and I had not much left after years of paying my business instead of my business paying me.
The decision morphed over time. At first I was open to something maybe part-time while I kept working on my business. Then I thought my business would be a side-hustle or hobby I’d do at night after a full-time job. Then I reached the final state: time to sell or close the business and do something else, for good.
The only other time I’d really looked for a job as an adult (and not a post-grad entry-level candidate) was in 2020, and boy, was that tough. I have never gotten less calls back. In hindsight, I only actively looked for two to three months max… not long. Since then I’ve learned the obvious truth: it oftentimes takes 6 months to a year to find the right fit and lock it down. This can only work if you’re patient, secure, and have planned and budgeted accordingly.
I was deeply, deeply insecure about how I presented as a candidate. I had failed. I was at what felt like the lowest point of my life. (Well, actually that was a few months earlier when I’d had to lay off the whole team.) It was very hard to envision myself as a desirable candidate and to convey confidence. It was even harder to find a concise way to articulate just how much I’d done as a founder— how many skills I’d built, how overqualified I felt to do things that technically had no place on my resume. When you’re a solo founder or operator, you are every department. I spent as many hundreds of hours in the last 2 years doing robust financial modeling as I did answering customer care tickets or designing a website or in the weeds segmenting email marketing campaigns on the daily.
But I dove in and went for it, and treated the job search process as what I’ve always known it to be: sales.