Finding the Struggle

“One day you’ll look in the mirror and ask yourself, “How did I get here?” And more importantly. “How do I get out?”….

….Give up this renaissance man, dilettante bullshit of doing a lot of different things (and none of them very well by real standards). Get to the guts of one thing; accept, without reservation or rationalization, the responsibility of making a choice. — “Twitching with Twight”

I’m confident that The New York Times’ recent article about the “wealthy and successful, yet miserable” is not likely to lead the average reader feeling sorry for your average Harvard Business School (or other top business school) grad. If you’re out of free NY Times articles to read this month ;-) , here’s the Cliffs Notes version of it:

• The author went to HBS and is a journalist, and is sort of giving himself a pat on the back for not going down the typical career path of his classmates. (It’s cool though, I’m sort of doing the same with this post)
• There’s a lot of people out there who make a lot of money and achieve professional status in the types of jobs that business school grads typically have chased after (McKinsey, Google, Apple, Hedge Funds, Private Equity, etc.), but they still get a sense of dissatisfaction from their professional lives.
• The author anecdotally describes a few of his classmates who didn’t fall into this pattern of professional dissatisfaction — the common thread among these classmates is that they were the ones who were passed over for the most aforementioned prestigious, high-paying jobs. The author calls these people “also-rans”. The author’s position is that the struggle or failure these folks had may have actually led to more satisfaction later.

My thoughts:

• The article is almost too short to take seriously, but it’s thought-provoking enough to elicit reflection.
• The article doesn’t explore other reasons for professional dissatisfaction, and doesn’t mention anything about how the “also-rans” were not just people that “failed” at finding the prestigious jobs (maybe they actually were the wiser, more self-aware students who weren’t seeking things like high salaries or status in their first jobs after business school).
• The article also only barely scratches the surface on the concept of grit or failure in the context of professional satisfaction.

Reading the NY Times article impelled me to write a little bit and share a bit of wisdom I’ve found (or maybe synthesized) in the last few years. I’m sharing this in the hopes it will help someone else.

I picked up this bit of wisdom from the first manager I had at Affirm, who will remain nameless (mostly because he wouldn’t want his name on the internet). In the context of the world we operated in (technology startups), his core career development advice to me was that the path to finding a meaningful career was (paraphrased):

Being a generalist is not going to take you anywhere. Career success at its core is about finding the thing that you don’t mind struggling with every day. It really doesn’t matter if there are other people in the world right now who are “better than you” at those things. Whether it’s software engineering, analytics, marketing, sales, finance, or whatever, even if you’re just starting out and you’re willing to struggle with it day in and day out you’ll not only get better and more efficient at it, but eventually you’ll have a reputation as the person who is good at doing at least one thing. Once you have that reputation, it’s much easier to get the professional leeway to expand into other functions or industries (in contrast to just being known as a “generalist”).

This strikes me as even more profound in the context of the NY Times article — having a high paying, high status job, to follow the herd of others might just be about struggling for all of the wrong reasons!

The truly most rewarding things that I have experienced in life have been the rewards that I’ve received from struggling (or applying stress) for a really long time in a consistent manner, and getting to actually see some long term results of that effort.

• Getting to deeply know someone through arguments, struggle, and overcoming challenges together, in such a way that you totally trust that person. (you could apply this to any relationship, romantic or platonic, professional or personal).
• Training for a sporting event or competition consistently for months or years at a time that results in a race/competition/performance that is a winning effort.
• Working on any other physical non-competitive practice (Weightlifting, gymnastics, yoga, surfing, whatever) to the point where you can hit a new personal record, skill, movement, or pose.
• Learning a new language or skill to the point of proficiency.
• Studying for a professional certification or test and getting a good result.
• The list goes on.

The point is not about accumulating accomplishments, the point is about the intrinsic reward that comes from working on something for a long-term time horizon, and recognizing results through that lens.

You could extend this line of thinking to a simple “audit” of your personal and professional calendar to see how you spend your hours, days, weeks, and months; for two things:

• Task orientation: How much of your time is spent working on something with a long-term orientation? How many hard problems are you working on? Are you struggling and stressing enough to grow (but not so much that you will be overcome by it)? Is your entire orientation about just getting tasks done to keep your boss happy or to meet some goal that means absolutely nothing in a long-term sense? Could you re-orient your own mindset or your actions so that they are long-term oriented? Can you do the same for your team or group of people that you lead?
• Long-Term reward recognition: Are you spending any time reflecting on the results of long-term effort or struggle, or giving yourself the ability to measure progress objectively? Wesometimes fail to realize our own accomplishments or development of skills because they can accumulate slowly, and we may need something external to show us how far we’ve developed — a test, a competition, or some other measuring stick or metric.