I Left Tech, Took 75% Pay Cut to Become a Hiking Guide

This as-told-to essay is based on a conversation with Cliff Goldstein, 40, who is based in Upstate New York and runs Hike with Cliff. His income, his former employment, and salary have been verified by Business Insider. The following has been edited for length and clarity.

In many ways, it was just a matter of time before I became a hiking guide.

Throughout my career, I’d dreamed of working in the outdoors. But I went down the road of working on Wall Street and then in tech, both of which came with a gradual sense of dissatisfaction.

I’d always thought that if I were ever in the financial position and had achieved enough in my corporate career, I could finally give myself permission to pivot.

In 2023, at 38, I did it. I had worked and saved enough to pursue my dream career, and now I’m leading groups on trails around the Hudson Valley and the Catskills. I’ve never been happier.

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I didn’t want wealth and success to stop me from taking a different path

My love of the outdoors started early. I grew up in the Bay Area, where weekends often meant hiking, biking, and exploring California.

In high school, I was an outdoor education teaching assistant, planning and leading trips for younger students. That was my introduction to guiding.

At Georgetown University, I developed interests in travel and other cultures. I spent a lot of time in Latin America, spending two summers and a semester abroad there during college.

In my later years at college, I realized I probably needed to pick a career. I did what others were doing — I interned on Wall Street. Once I’d graduated, I moved to New York and started working full-time at the now-defunct Credit Suisse. This was back in 2008, during the financial crisis.

In 2010, I started working at Goldman Sachs, back in San Francisco, primarily in wealth management. I enjoyed aspects of the job, and it interested me intellectually. I had some good experiences in the finance world, in general, but it was pretty clear early on that it wasn’t what I wanted in the long run.

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For starters, the culture wasn’t a natural fit for me. The lack of work-life balance was a huge part of that. I also came across a lot of people who didn’t seem thrilled with their lives, but were too bought into a life of wealth and success to take a different path. I didn’t want that to be me.

After joining three early-stage tech startups, it was time for a break

I wanted to do something that felt truer to me. At the start of 2013, at 27, I decided to make my first career pivot — entering the tech world.

I was living in San Francisco during the glory days of Bay Area startups. As an outsider, it looked like people in tech were enjoying their lives more than those in finance. There was excitement, energy, and lots of VC money flying around. I wanted to be a part of it.

Given my background, it made sense to go into financial technology. I networked my way into a job. The first early-stage startup I joined was NerdWallet. I stayed for five years.

I joined another startup for two years and then another for two and a half, both in the Bay. I joined them all at relatively early stages, helping them grow. I was fortunate enough to make some good decisions about picking the right startups, which were on a strong early growth trajectory.

It was intense, dealing with the dramatic changes that early-stage startups often go through. After my third, it was time for a break. I took a nine-month sabbatical, during which I assessed some other career options.

I wanted to do something that would make me happier

I ultimately decided to join one last startup in mid-2022 at age 37.

Admittedly, I took the job at Mercury, another fintech company, because it was doing well, and it offered a very high salary. I don’t have a single bad word to say about it. The reality was that it was simply not what I wanted to be doing anymore. I wanted to be doing something that would make me happier.

My salary was more than $250,000 a year. Fortunately, I made some intelligent investment decisions and saved, which allowed me to leave the industry and go into something I’d love, albeit with lower earning potential. This was in mid-2023, when I was 38.

I didn’t have a set dollar amount I needed to save to leave; it was more a state of mind. I spoke to financial advisors, and it helped that I have a loving wife who supported me taking this leap.

From 2022, we’d started spending more time in the Hudson Valley, where my wife’s family lives. It eventually became our home. It was the perfect place to start my hiking guide business — the Catskills and the Hudson Valley are right next to each other, and both are beautiful.

Early on in the business, other guides in the area provided me with knowledge and connections. I also built partnerships with hotels nearby. I wouldn’t have been able to build a client base so quickly without my business experience.

The hiking guide business is not a big money-maker. I’m on pace to make about 25% of the salary I would have kept if I’d stayed in tech.

Nowadays, I’m more mindful of my spending, even though I never lived luxuriously. I didn’t need to change my lifestyle too dramatically. My wife’s job gives us health insurance, and we live in a lower-cost area than San Francisco or New York City.

Corporate groups are what I earn the most from — they come to the Catskills on organized days out from the city. Often, they’re just so thrilled to have a day off from their screens. I can tell from the giant smiles on their faces.

A lot of them work in finance or tech, like I did. They enjoy hearing the story of my career pivot.

I may be earning less nowadays, but it’s worth it to see the awe on my clients’ faces when I take them to beautiful places. Seeing the connection they feel to nature in a place I’m lucky enough to call my home outweighs any of the financial success or security I might have felt if I’d stayed working in tech.