Don’t Quit Your Day Job

Michael (my then-boyfriend, soon-to-be-fiancé, later-to-be-husband) held up his phone and triumphantly showed me his new countdown clock:

256 days, 8 hours, 57 minutes

Even though I had gushed to him at our two-year date-i-versary the week before that I was supportive of his leaving his well-paid job as a management consultant to follow his dream of being a stand-up comedian, I have to admit that I wasn’t totally on board with the idea of losing half our security for the future. Most people don’t quit their day jobs until they’ve seen some tangible success in their side business; and while Michael was a funny and talented guy, he was still very much an amateur comedian. He hadn’t built up a followership, he wasn’t booking paid gigs, and he wasn’t even headlining often in unpaid gigs.

But it was admittedly a chicken and egg situation. He couldn’t keep up this 50-hour-per-week corporate job and devote enough time or mental energy to stand-up to even see if he could be successful. If he felt that this was something he had to try or would regret it for the rest of his life, then he needed to go for it 100%. He was 32, ten years older than most people starting out in this type of career, and there wasn’t time to keep slowly working at it on the side. It was all or nothing, and nothing was not an option for him. I got it, even if I didn’t completely like it. So I smiled (grimaced), gave a thumbs-up to the countdown clock, and thought, well at least he had the good sense not to resign until he got his annual bonus.

This eight-month transition period also gave me plenty of time to break the news to my parents that their only daughter was planning to commit her life to a man who was going to quit his respectable job and try to make it in an occupation with a near-0% success rate. My parents were two sensible and responsible people who thought that one should find a good profession and stick with it for the next 40 years until it was time to retire. And that if you did need to leave a job for any reason, you should never ever do so without already having a new one lined up. So how about leaving a job with no new one lined up, only a pipe dream with a fuzzy career path, no near-term income and no guarantee of success? This was going to be a tough sell, if I wanted them to continue liking Michael and welcome him into our family when he finally did propose.

I tried to help them understand that people in my generation do quit jobs to pursue dreams, and do not stay in professions that make them unhappy. (My dad’s response: an article titled “Why ‘Follow Your Passion’ Is Bad Advice”.) I also assured them that Michael was a smart and sensible person too, and that he wouldn’t keep trying year after year to make it as a comedian if he wasn’t getting anywhere with it. (Right?? At least that was my understanding…) But even if this just led to a more creative career path than management consulting, that was worth a shot, instead of feeling unfulfilled for the rest of his life, stuck on the hamster wheel that is Corporate America.

I myself had gone down the path of marketing, and it was a good profession, but it wasn’t what I was passionate about and I couldn’t imagine doing it for several more decades either. I also would have loved to pursue a dream job – something that I truly enjoyed and couldn’t wait to get up in the morning to do (what a concept!) – but I hadn’t yet gotten up the courage. So, good for Michael! Maybe he’d even inspire me to give it a shot. But not right now – he had called dibs on dreams, and I was too practical and too risk-averse for both of us to quit our jobs and make no money for an indefinite period of time. No, that definitely could not happen. There had to be a plan if this was going to work. And it was for me to support both of us with my marketing job, while Michael threw himself 100% into trying to make the transition from open mic hobbyist to professional stand-up comedian.

That plan would have worked just fine, if not for one tiny little thing…

I got laid off. Four months (112 days, 2 hours, 34 minutes on the countdown clock) before Michael was planning to leave his job. Oh nooo. This was not happening. It was the first time I’d ever lost a job, and the timing couldn’t have been worse. Suddenly the promise of a steady paycheck had disappeared, and the future didn’t seem so certain.

Normally I would have just rushed right out to find a new job, but my recent career choices had felt like giant mistakes in hindsight – namely, leaving a great job at a large tech company to join the San Francisco startup scene, which did not end up being my cup of tea – and I wasn’t feeling as confident about my place in the working world as I had a few months earlier.

So what to do now… Should I just return to a large tech company? Most of them were in Silicon Valley, and I couldn’t face the long commute again after having done it for four years. Or should I take this as an opportunity to try an entirely different career? People always talk about how getting laid off gave them the freedom almost permission to try something different, which they never would have done if that had meant voluntarily leaving a good job. The thought was enticing, but I didn’t have too long to figure it out, as Michael’s “Quit My Day Job” countdown clock drew down.

85 days, 4 hours, 27 minutes, and counting… Crap.

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