How to have a “successful career” on your own terms

Don’t get trapped by someone else’s definition of success.
Don’t get trapped by someone else’s definition of success.
Image: AP Photo/Robert F. Bukaty
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Two years ago, I was living the life I thought I wanted. I had a prestigious consulting job working with CEOs and a clear path to a successful life–one where I wouldn’t have to worry about money or future career options.

But it was never my path. I had opted into a default path, a story of success. My path was filled with prestigious companies and degrees, and because of this, it was even harder to leave. How do you give up on something that so many people want?

Many of us are trapped in these kinds of default paths. We make an initial decision that sends us on a journey and then ten years down the road we poke our head up and wonder “how did I get here?

This is what happened to me. In 2017, I left the default path of success. At the time I thought I was headed toward a slight reinvention of my career, by becoming a freelance consultant. What I discovered instead was that I was in the process of not just reinventing my work identity, but my entire life.

Three questions have guided me as I’ve actively created a new path that may not make sense to other people, but brings me closer to living a life of which I am proud.

Question 1: How much money do you really need?

The first freelance project I landed was based in Boston while I was still living in New York. Working remotely from my New York apartment, I quickly realized that I could be sitting anywhere–so why was I sitting in the most expensive place in the US? If I moved to Boston, I immediately could save at least $1,000 a month.

In preparing to move to Boston, I started questioning everything. Does someone in their 30s really need a nice apartment? Why am I casually dropping $100 on dinners when I’m not a foodie? While I had never been an excessive spender, my steadily increasing salary over the years induced a certain type of ignorance to what I actually needed or even wanted.

I looked at money in a new light. Instead of a steady monthly income appearing each month, I had to find paid work to support everything I spent. Spending more meant I had to land more work. It also meant that if I spent less, I could work less. This was not an option available to me within the context of full-time employment.

The default path taught me that a six-figure salary was success, but with my new expectations, I realized my real dream was a modest five-figure salary and more “non-work” time to experiment and create.

Question 2: What kind of work are you drawn to?

I knew that self-employment was going to involve constant reinvention and alignment with the type of work that would energize me.To achieve this, I couldn’t just work all the time. I would  need time and space to create, experiment, and reflect on what kinds of work I was being drawn to, what kinds of conversations I wanted to be having, and what kinds of communities I wanted to contribute to.

After six months of steady project work, I felt a pull towards a number of ideas I was working on. I decided to take three months to experiment with these ideas. I ended up launching a podcast and tools to help people become self-employed, and I started to take my writing seriously for the first time.

While nothing I created was very good at first, I discovered a different type of work: The type of work that calls to you instead of the type of work that is assigned to you. There is a subtle difference, but it leads to a powerful feeling of discovery, curiosity, and imagination that I didn’t know could co-exist with work. As anyone who has been drawn to something knows, you can’t just turn off that flame.

I wasn’t sure where I was headed, but I knew I needed to keep going.

Question 3: How do you want to spend your time?

A continued reflection on my relationship with money and moving toward the work that lit me up made living abroad attractive. It was something I had never done earlier in my life and could further lower my cost of living while learning even more about what kind of life I wanted to build. I decided to move to Taipei for three months.

This was a hard decision for me because by that point I had built a life which allowed me to spend more time with the people that mattered to me. Working less was not just about finding time to work on creative projects, it was also about spending time with the people I loved.

In the summer before I left for Taipei, I set a goal of spending 50 days at my family lake house, specifically to spend time with my 89-year-old grandmother, who says things like “if you stop learning, you might as well be dead.” She’s the best.

In my previous path, I felt lucky if I could sneak a half-day off on a Friday for a long weekend, but because I questioned the default path, I was able to spend many priceless mornings sipping coffee with my grandmother overlooking the calm serenity of the lake.

Can you see your path laid out ahead?

Should you follow my path? Of course not. But perhaps you can start by asking yourself these three questions and reflecting on whether you are actively choosing your path or opting into a default path with someone else’s definition of success. David Whyte put this most powerfully when he wrote in his book, The Heart Aroused: Poetry and the Preservation of the Soul in Corporate America. He wrote: “If we can see the path ahead laid out for us, there is a good chance it is not our path; it is probably someone else’s we have substituted for our own.”

Paul Millerd is the creator of Boundless.