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When to Make a Career Pivot

The author of 'Pivot' says timing is everything

(Adapted from Pivot: The Only Move That Matters Is Your Next One by Jenny Blake, in agreement with Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House. Copyright © Jenny Blake 2016.)

Many people hit a plateau in their careers and feel an inexplicable urge to do things differently. The way they have been working is no longer working for them. They’ve hit a pivot point in their careers.

I define a career pivot as doubling down on what is working to make a purposeful shift in a new, related direction. Pivoting is an intentional, methodical process for nimbly navigating career changes.

One of the biggest questions that troubles people during a career pivot is “How do I know when it is time to launch?” The answer will be different for everyone, but there are a few general indicators.

One of the biggest questions that troubles people during a career pivot is "How do I know when it is time to launch?" There are a few general indicators.

FiPivot_jacketrst, clarify your Launch timing criteria as objectively as possible. You will have a clearer idea for when to launch based on reaching certain thresholds, and will know when you need to adjust if your experiments are not going as planned.

Below is an overview of common Launch decision-making criteria. Note the factors that matter most to you, then rank that list in order of importance: critical “must-haves” for your decision, “nice to haves” and “don’t matter.”

Financial Benchmarks

  • Money saved (Pivot runway): Ideally, you should have at least six months of savings to see you through a launch.
  • Money earned (When my side hustle earns X dollars or more): Although your side hustle earnings may not yet equal your salary, analyze their likelihood of generating cash flow.
  • Stay until OBO (Or Better Offer): Only change if a more enticing offer appears.
  • Specific size compensation: What is your minimum threshold for accepting another offer? Can an offer provide other benefits such as more vacation time, flexible hours, or remote workdays to make up for the lower salary?
  • Financial incentive tied to a date (When I get my bonus, or when this deal goes through): If you have a bonus coming that you have worked hard to earn all year, it behooves you to stay to receive it.
  • Outside funding approved (When I get a bank or family loan, or venture capital or angeI funding): Consider whether you really need funding or a loan to proceed, or whether it is a form of procrastination or if then linear thinking.

Date-Based Timing

Many pivoters first decide what other criteria impact their decision; then by giving themselves a deadline, they become clear on when to make it happen.

  • Complete and Launch X project at work: If you have been working on a big project at work, it is important to see it through, so you don’t burn bridges by leaving others in the lurch. That said, sometimes projects take years to complete. In that case, identify the work milestones you can complete, and clearly document your role and any unfinished business to ease the transition for others.
  • Take X months to explore, or take a sabbatical: Buy yourself time to breathe by setting a future date when you will revisit the do-or-don’t launch question.
  • Make a Launch decision by X date: Having a firm “zero hour” deadline can be freeing, and an important way to inspire action, knowing that you may never feel fully ready.
  • Make the move by X date or leave no later than X: Once your mind is made up, it is time to take action. Set a deadline for when you will launch.

Progress Milestones

These items add a layer of depth and specificity to the financial and date-based criteria:

  • Build X prototype in my business: Complete a project milestone that is a critical precursor to launch.
  • Land X new clients: Indicates that the new direction is viable and income generating.
  • Planning readiness: Have all the steps in place and know the ideal outcomes and make-or-break markers in worst-case scenarios.
  • Platform reaches a certain size: Will lead to more opportunities and connections.


What struck me as particularly interesting in the interviews for this book was how many people said that, in the end, their decision came down to physical cues. They would get a gut feeling or if they didn’t heed those warnings, their health declined until their body started screaming to make a change.

  • Gut feeling: ”I’m ready” or “I will know when I am ready.”
  • Maxed out: “I am miserable.” “Any change is better than this.” “It is no longer healthy for me to stay.”
  • Gave the last gig my all: “I know I tried everything I could.”
  • Willing to go all out: “I am ready to give this next thing everything I’ve got, no matter what happens.” “To try and risk failure is more important than not trying at all.”

In Others’ Hands

Some big decisions lie outside of our immediate control. For instance:

  • “Gatekeeper” industry approval or offer: You get a book deal, music contract or grant funding.
  • Acceptance in an application only program: You have been accepted by a graduate school, The Peace Corps, Teach for America or a startup incubator or accelerator.
  • Partner earns X or completes Y: Your partner gets promoted at work, finishes graduate school or finds another job.
  • Awaiting full agreement or support from partner and/or other family members.

Of all the criteria in this section, the one that seems to cause the most stress is waiting for full agreement from family members. Determine whose approval is critical to your decision and whose is nice to have, even if disappointing not to receive. My mom and I did not see eye to eye on my decision to leave Google when I did. We still don’t! Although I can understand her point of view and wholeheartedly respect her advice and career choices, I also know that my process and Launch timing decision was the right one for me.

After reviewing all the Launch timing criteria, you will know what critical factors your final Pivot steps hinge on. All that remains is working your way toward those benchmarks, adjusting as you move along and then going for it.


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