It’s been about a month since I last posted here, and let me tell you: that month flew. When we last left off, I was in a bit of panic mode. I’d just gotten laid off from a job that I thought I’d be spending the next few years at and I dove into furiously interviewing with companies all over NYC hoping to find a quick landing. I spent hours every day emailing, following up, being phone screened, hopping from neighborhood to neighborhood meeting people, interviewing, getting advice, and basically going overboard and seriously stressing myself out.
Coincidentally, I’d had a trip to Boston planned to see some friends I’d long promised to visit. That came with about 4.5 hours on the Amtrak each way. And we all know what happens when I spend too much time disconnected from the internet and Thinking. I come to terms with reality, that’s what!
I took my foot off the gas a bit. I was waiting to hear back from 2 companies, one of which I’d been eyeing for a few years and would have said yes to in an instant. Sadly, though, that one didn’t work out. Combined with my Thinking on the train, I realized: hey, why am I in such a rush? And more importantly why am I willing to settle for something that I don’t actually want but is just the logical, easy next step?
I did some bank account calculations and concluded that, with some careful spending and some side income, I could make it to the end of the year. I’d done it before. Many, many times. Those few months would give me the space to sort stuff out and really try to do what I’ve been trying to do all along, the thing I’ve been taking two steps forward, one step back on for the last two years: being self-employed.
And, as a Plan B, the end of the year is much “easier” to find headcount at larger companies that are looking for new hires to onboard in January, so if my plans failed, I’d actually be in a better position to find a job later this year than I am in the middle of the summer. It’s all about timing. At least that’s what I convinced myself of.
Around mid-August a series of serendipitous events started to unfold. Apart from going to Boston and getting my reality check, I also happened to sync up with an old friend/mentor who happened to have some freelance work that needed to be done. I dove into that project, letting me work completely remotely, and may (fingers crossed) have some future work lined up as well.
Meanwhile, during the last few weeks of August, I’d planned to take a vacation with my cousins and then spend some time at my mom’s house at the Jersey Shore. My freelance gig started just before I left and I managed to set up shop wherever I was - a hotel lobby, the back seat of the car as we drove from LA to Las Vegas, my mom’s yard. I was living the dream.
All making me realize that this is what I’ve been wanting all along and I’m closer to achieving it than ever before. Being the master of my own calendar and my own destiny. Being able to work from whatever corner of the planet I happen to be in. Having enough flexibility that I can function well and do my job from anywhere I have a wi-fi connection. Working on different projects. Learning new things all the time.
I keep falling into the ease of working somewhere “stable,” but if the last few years have had any lesson for me, it’s that startups are really no more stable than anything I could attempt to do on my own. Part of me likes to think I’m on the pioneering wave of this type of life. That offices are a vestige of the past and I’m just ahead of the curve and the rest of the world will think I’m not insane in 10-20 years. Or maybe the real world will be the one with the last laugh. But this is something I know deep down I need to pursue and see where it ends up.
So maybe I’ll be eating my own words in 6 months. Or maybe I’ll be writing my 6-month update post from a farm in Colombia or a couch in Boulder. Maybe I’ll be sitting in my apartment with my PJs on already 4 hours into the day. Or maybe I’ll be typing it away during my lunch break at whatever company I end up joining because this whole experiment was a massive flop. Who knows. I’m excited to find out.