A New Approach to Goals: How Are You Trending?

Jeremy Schwartz

Discussions around career and business planning tend to boil down to a seemingly straightforward three-step process: First, set a clear goal. Second, chart a course to that goal. Third, keep your eyes on the fixed prize.

This approach assumes a few things that have never been true for me, so it’s always struck me as doomed to failure:

You can articulate a clear goal… But sometimes you don’t have enough information or experience to do so and all you’ve got is a vague inkling of where you want to go.

You can identify a path to that goal… But if you’re trying to do anything new or innovative there may not be any path or even a first step in the right direction.

Your goal is a fixed North Star… But unless you’re an athlete headed to the Olympics, your goals will evolve as conditions change and you mature.

So if total clarity, straight lines, and North Stars aren’t realistic, what should you do?

My answer: Focus on trending in the right direction.

I use this approach for big questions (What am I doing with my career?) and small questions (What should I do at work this week?) and have found it to be much more useful than the single-minded-commitment-to-a-clear-goal strategy. Trending doesn’t excuse you from thinking deeply about who you are and what you hope to achieve but its inherent flexibility and squishiness makes it more powerful, durable, and robust than a simple roadmap.

Stepping back a bit….

I started my career at a large corporate law firm. The firm offered prestige, rigorous training, good money, and a steady stream of inbounds from headhunters. It was a great first job for a lawyer and I was glad to be there.

Despite all that I faced two major problems a couple years into my practice. One, I didn’t want to be a lawyer. Two, I didn’t really know what I wanted.

The best I could come up with was the vague goal of wanting to make a “move to the business side.” That was a phrase I heard around the office and in the cafeteria but, to be honest, I didn’t know what it meant. And how could I have, considering that I had spent my entire training and career operating in a very narrow band? I was just starting to get a handle on what being a lawyer meant, so it was no wonder that I couldn’t articulate what I really wanted to do.

Nevertheless, a “move to the business side” felt directionally accurate.

After a few months of failing to find any direct routes to the “business side,” I decided that taking a small step in that general direction was my next best option.

This led me to accept a one-year gig at a tiny private equity fund located in Sydney, Australia. The fund offered terrible pay, weak benefits, and no job security. It was a worse job than the one I had at the law firm in almost every way, but it had one thing going for it: I’d have the opportunity to work on “deal sourcing” and it felt like an opportunity to start trending in the right direction.

A couple things happened during that year in Sydney.

First, I took (and passed!) the first part of the Chartered Financial Analyst exam series. I never expected to complete the CFA series or work as a financial analyst but the test covered a lot of the same academic areas as an MBA program and I thought it would reinforce my trend towards business. I was in the process of reinventing myself professionally and this was a bona fide to prove that I was more than just a lawyer who said he wanted to do business.

Second, I got to look closely at how actual operating companies operate on a day to day basis and I found it fascinating. The companies I was analyzing were insurance companies and that was not an industry I was interested in but that new information helped me refine my goal from “moving to the business side” to “working at an operating company.”

Third, I learned how to surf. This has nothing to do with my career trajectory but it was a nice knock-on effect of stepping off the well-worn corporate law track!

When my wife and I returned home to New York, I trended further away from lawyering and tacked away from private equity and insurance by working my way into the burgeoning technology scene. This involved going to lots of events and having lots of coffees, some of which were on-point and some of which weren’t. This involved starting a couple businesses of my own and getting to know the roles that exist at tech companies. Not every Meetup was worthwhile, not every coffee was interesting, and none of my businesses were particularly successful, but I could feel myself continuing to trend in the right direction.

These experiences led me to reformulate my goal as “doing business development at a growth-stage technology company.”

Almost two-and-a-half years after kicking off my trend away from lawyering I had transformed myself into a viable candidate for a business role at a growth stage company just at a time when Squarespace, a do-it-yourself website builder, was looking to fill that sort of role. I was invited to apply by an acquaintance and was hired to join the team.

I’ve been with Squarespace for nearly three years, and as I’ve had new experiences, I’ve continued to update my personal goals and find new opportunities to trend toward them. I’ve also brought this “trend don’t target” philosophy to my day-to-day work and have applied it to projects and work that involve multiple people and teams.

The flexibility and forgiveness of a trend-and-revise strategy has helped me build a career on the ever-shifting sands of a growth-stage company to a degree that a set-and-target strategy never could.


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