Reflecting On 20 Years Of Backwards Financial Moves

Stocks fell last week with the S&P 500 shedding 1.2% to close at 5,123.41. It was the worst week since October. The index is now up 7.4% year to date and up 43.2% from its October 12, 2022 closing low of 3,577.03. For more on market volatility, read: Even strong stock market years can get very stressful

I celebrated my birthday on Tuesday. And once again, I found myself reflecting.

A little over 13 years ago, I quit a stable well-paying job with benefits to blog about markets as a freelancer. Overnight, my income effectively went to zero — but that was part of the deal.

Unfortunately, things only got worse from there. I was horrible at budgeting. I did a poor job of securing enough freelance work to keep me afloat. At one point, my biggest client cut the rate they were paying me in half with little warning. And in about four months, it became clear that I was going broke.

In retrospect, it was a great learning experience. I learned about the challenges of finding work as a freelancer with little writing experience. I learned how quickly things will fall apart when your income relies too heavily on one client. I learned how much of a nightmare it can be to be responsible for things like accounting and IT. I learned how nerve-racking it can be to exist without health insurance. Importantly, I learned what I was really capable of when left to my own devices.

I have no regrets. While that decision may have put me on the path to short-term financial ruin, it also put me on the path to longer-term happiness and financial security. That September, I got hired as markets editor for Business Insider. And the rest is more or less history.

It turns out that a lot of my career history involved seemingly backwards financial moves. Here’s a quick timeline and summary I recently shared on X:

• 2004: 📈 got my first real job

• 2005: 📉 quit job for lower paying job

• 2006: 📉 quit job for similarly paying job in a much more expensive city

• 2010: 📉 laid off

• 2010: 📉 got job that paid less than previous job

• 2011: 📉 quit job to freelance

• 2011: 📉 got job that paid less than previous job

• 2016: 📈 quit job for higher paying job

• 2021: 📉 quit job for lower paying job

• 2021: 📉 quit job to start newsletter

Yes, it is true that there’s only been one time where I’ve accepted a job that offered more than what I was getting paid at the time. But in case you didn’t figure it out, I was getting raises and promotions at many of these jobs.

I’m not saying this to gloat (and to be clear, being a self-employed newsletter writer is anything but a walk in the park). Rather, it’s just been my experience that opportunity has often been defined by much more than what the next job was willing to pay on day one.

Great Luck And Incredible People

I’m aware of the fact that any success I’ve had wasn’t just the result of hard work and intelligence. There are people who work way harder than me, and there are a lot of people who are way smarter than me. Way smarter.

I’ve definitely benefited from having great luck.

I got my first big job through someone I got to know at an afterwork dodgeball league. Eight months after our first meeting, he emailed me out of the blue about a job vacancy on his team.

I got my first big freelance writing client through a colleague of a friend of a friend, all of whom I met by attending the alumni happy hours for a college I didn’t attend.

Another pivotal job came from someone who poached me. What was unusual about this was this same recruiter actually tried to poach me for that same job years before. The first time I spoke with them, I said no. The second time years later, I said yes.

I’ve also been extremely lucky to have generous mentors and brilliant colleagues along the way — people who seemed genuinely interested in lifting me up and celebrating my wins. These people exist.

If there’s one smart decision that I’ll take credit for, it’s the decision to move to NYC. Yes, it’s competitive as hell here. And yes, people who already have access and money often have an upper hand. But still, opportunities seem to spill out onto the streets here. And while there are plenty of people here who don’t care about you unless they can use you to advance their own interests, there are also a lot of people who’ll help rocket your career.

Zooming Out

Everyone will have their own unique path. Some will find more success than others.

In my experience, few things ever go as planned. Much like the stock market, careers don’t follow smooth paths up and to the right. And often, the surprises are no fault of your own. Sometimes your luck is bad. Sometimes your luck is extremely good.

I do think that just because something doesn’t work out doesn’t mean that the decisions that got you there were regrettable. At the very least, you hopefully learn something. And maybe those lessons help you make better decisions in the future.

All that said, this is coming from someone who hopefully has many years ahead of him. That means there’s plenty of time for things to go horribly wrong. Or maybe I’ll get lucky again.

A version of this post was originally published on Tker.co.