'Fail Early, Fail Often — and Know When to Pivot'

It's a time of career upheaval. From the mass tech layoffs to the post-pandemic recalculation, I know many people who are thinking, "what next? Where does my career go from here?"

One book that I read over the past year has massively impacted how I’m thinking about trying new things, failing — and then trying again is Range by David Epstein. While there are a lot great stories from the book, one big takeaway for me is how valuable having a wide range of experience is no matter what your profession is — and I think it can be valuable for the job seekers and career pivot-ers (myself included!) out there.

In Range, Epstein challenges the conventional wisdom that specialization is the key to success in today's highly specialized world. (Think of that hyper linear career ladder and specialized Master’s degrees.) Instead, Epstein argues that having a wide range of experiences and skills, even if they initially seem unrelated, can actually lead to more successful and fulfilling career paths. Things like having a creative hobby, learning to code on the side, teaching English abroad, and even a layoff don’t have to be thought as anecdotal experiences or even detours on your career journey.

It makes me think of this graph that’s gone viral on LinkedIn:

In that light, maybe the times where we explore unexpected paths or new side hobbies and especially the times where we try new things and fail are really essential parts of becoming the people we want to be. Here’s why: we learn about ourselves only by living.

"Learning stuff was less important than learning about oneself. Exploration is not just a whimsical luxury of education; it is a central benefit," Epstein writes.

In times of career transitions or setbacks, it's easy to feel like you've failed, stumbled, or missed the mark for your professional goals. But what if you could use this as a rebuilding time to build something even better?

Here are some of my other favorite takeaways from Range:

1. Fail early, fail often — and know when to pivot

Many of the most successful leaders and artists fail... a lot. And that's not news. You've probably read VC thought-leaders preach on how critical failing is to building something that lasts. The key here is to use that point of failure to channel a new experience.

In the context of layoffs and career pivots, that means being able to let go of the career path that you envisioned. Maybe even your 10-year plan. The beautiful, frustrating thing about life is that it doesn’t work according to your calculated plans. You zig and you zag, you take one step forward and then seven steps backward. Sometimes even you jump to a new path altogether. Many of us are finding a new path, whether we chose to or not.

Instead of viewing this moment as a setback, you can see it as a new opportunity to pivot. Are there new skills you're hoping to learn? Or an area you would like to explore? Having the freedom and ability to feel like you are starting from scratch can actually be a great building block for the next phase of your career.

Range cites Vincent Van Gogh as one highly successful artist that failed repeatedly. By the time he was 26, he had pin-balled from one artistic passion to the other and had failed stints at teaching, art dealing, pastoring, and bookselling. He enrolled in art school at the age of 33 (and at the time, he was told it was "too late" to begin a new career.)

There's an art in picking yourself back up and forging ahead. And you are likely to end up in a better place than you started.

Epstein also quotes Seth Godin on the act of quitting often. He argues that 'winners' "quit fast and often when they detect that a plan is not the best fit, and do not feel bad about it. We fail "when we don't have the guts to quit."

2. There's no such thing as a late start

A study conducted by Todd Rose, director of Harvard’s Mind, Brain and Education program, and computational neuroscientist Ogi Ogas, sought to explore the careers of successful people who took 'unusually winding' paths. They wanted to find people who ended up fulfilled and successful and who had arrived at that point circuitously.

They surprisingly found that this wasn't the exception — it was the norm for many people who had found success. The vast majority of their subjects often had several pivots in their career where they started something completely brand new or left field. Almost all of the participants, felt like they had made random jumps or had a late start to their current careers. And yet it all ended up leading them to a thriving place.

"Maybe we don’t excel in spite of late starts, but because of them," Epstein writes.

Hopefully, this is a balm for anyone years into a career and wanting to make a significant change. It's never too late.

3. Learn the art of short-term planning

Instead of agonizing over your 20-year plan and each step that you have to make in order to get there, it's helpful to approach career decisions on a short-term basis, Epstein argues.

Focus on some key questions and ideas, he suggests:

“Here’s who I am at the moment, here are my motivations, here’s what I’ve found I like to do, here’s what I’d like to learn, and here are the opportunities.

Which of these is the best match right now?”

Maybe you started out on a career path that felt secure and certain but didn't turn out to be what you envisioned. Whether that was a decision you made or something forced on you via a layoff, you can write the next chapter new.

“Our work preferences and our life preferences do not stay the same, because we do not stay the same," Epstein writes. "We learn who we are only by living, not before."

Reading this book challenged me to reframe how I am viewing this moment in time in my career. Do I see it as a setback or a ledge that can propel me in an entirely new direction? This thinking brings a world of opportunity with it.

Here’s to failing early, failing often — and knowing when to pivot.

As for me, I’m fully embracing my Pivot Era. From freelancing to living abroad, I’m set out to challenge the goals I made for myself in the past and how I have previously envisioned success.

I’m excited to dive into this topic more in next week’s newsletter. As always, if you think of someone who might enjoy this newsletter please pass it along for me. 💌