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Career pivot? You’re more prepared than you think

Preparing for a career change: how to know and leverage your value
Career pivot? You’re more prepared than you think
Illustration: Siah Files (In-House Art)
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After coaching hundreds of people in my career, I’ve found there are two questions we all seem to ponder over and over:

Is this what I should be doing with my talents?

If so, what should I be doing next?

These tendencies to question how we feel, evade satisfaction, and desire more aren’t new. They’re cyclical.

Something may shift in your professional world, and the fabric of your life starts to feel tight and itchy. Sometimes it’s the same work trigger, like being overlooked for your contributions. But typically, it’s numerous shifts: a disengaged manager, a boring workload, or a feeling that you’ve stagnated. Your personal life can ignite a sense of unrest, too, from milestone birthdays to new relationship dynamics.

In my work as a coach and advisor, I’ve seen people spend too much time asking Is this the right time for a pivot? And am I ready for it? If you’re craving a pivot, don’t get stuck in pondering purgatory. With a few tools, you’ll find that you’re far more prepared than you think you are—and show others that you’re ready for a full turn.

The power of the past

Your unique experiences and knowledge make up around two-thirds of your total lifetime wealth, and the skills you have contribute nearly half of that value. Yet most of us don’t understand what we’ve done to add value in the jobs we’ve had over our lifetimes.

While it’s valuable to audit your experiences in your current role, we should go all the way back. Want to know what I learned from Taco Bell at 15 years old? How I really used my project management certification? What I learned from the failure of a large tech implementation I led 18 years ago? I can tell you because I worked through an exercise I created called the 3 x 5 = 3. The exercise has you write down 3 answers to 5 prompts, then summarize it all in 3 major takeaways.

The exercise: 3 x 5 = 3

First, write down every job you’ve ever had.

For each job, write down:

3️⃣ things you learned or experienced

3️⃣ projects you worked on or led

3️⃣ skills you gained

3️⃣ things you did well based on your learnings, projects, and skills

3️⃣ things you could have done better or differently based on the same

Once you’ve put together the whole picture of your experiences, review your work and consider the total value you brought to the role. Summarize each job into 3️⃣ key contributions you made.

Reading the tea leaves

Self-reflection is going to be helpful for you in this exercise, especially if you give yourself a little space for that final step—perhaps a few hours or even days. Set aside time on your calendar to return to it.

When you come back to the exercise, spend time with the results in their entirety. Read them all slowly, then linger on the last one: the 3 key contributions you made in each role. These summary statements act as your elevator pitch for a pivot, with the additional reflections adding specificity. I found that the more I reviewed my results, the easier they were to recall and share with confidence.

Ask yourself the following questions:

  • As I look at the key contributions over all of my roles, what trends do I see?
  • Do the trends point to any obvious next steps, jobs, or industries?
  • What skills could be transferable for a pivot?
  • What other industries, companies, or jobs could leverage contributions like mine?

Prepare for the pivot

Whether you’re already feeling the itch to pivot or just curious about what’s next, here’s the good news: you have options. The freedom of a pivot is that it’s not the defined career ladder we were taught to envision. It can also be a left or right turn, or a leap across.

So start with the most macro category: where you’ll leap.

Same company + a pivot: Most of my career pivots have come when I was already at a company. I’ve never been a recruiter, but I pivoted from an operations role to head of recruitment because I knew and promoted my transferable skills.

I learned from failing and from changing organizations like it was my job—because it was—that the grass isn’t greener on the other side. It’s just a different color, and there is always poop to pick up in the form of its problems. So unless the grass you’re currently squatting in is toxic (and some is), you can find value in staying where you’re at and gaining experiences where you know the terrain.

New company, new role: Sometimes it’s just time to make a break. Many people change jobs at their mid-career point, but their motivators vary. Trust in yours: you don’t have to justify your jump.

Smart companies and recruiters are pretty good at identifying transferable skills, and the 3 x 5 = 3 exercise can help you find yours on your own. Are you awesome at time management, no matter what they throw your way? Have you been told your EQ is off the charts? Are you a fierce prioritizer that sets the example for others? You’re identifying skills that you’ve consistently performed well over the years, and you can use them to make your pitch to pivot—wherever you want to land.

Your pivot potential

Your potential to pivot is high. And if you didn’t think so before, self-reflection and a few thoughtful hours should boost your confidence. Embrace your value, and you’ll find impact in what I like to call your best next.

Put me in, coach, I’m ready to play

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🛑 5 ways to cope with mid-career stagnation

You got The Memo

We’re rooting for you, whether you pivot or stay put. Send questions, comments, and tips for reworking work to This edition of The Memo was written by Anna Oakes and edited by Gabriela Riccardi.