Career Pivot is possible: The No-Fear Guide

If you think that career pivot is like aiming for the moon but landing your shot right back on Earth (I just made that metaphor up, but you get it), think again.


Have a look at these successful individuals who probably never even thought they would end up where they did:

Arnold Schwarzenegger 

From Body builder to Actor to Politician (Governor of California)


From regular lawyer to one of the best leaders the world ever had

Ray Kroc

From driver/pianist/salesman to Maccas business tycoon

For a more local example, there is a huge increase in what is called seniorpreneurs in Australia, or Australians over the age of 55 starting their own businesses. It’s now seen as the fastest growing segment of entrepreneurs in the country.

What do these tell us? That starting a new path in the middle, or even at what looks like the end of a career timeline, is something that has happened before and is possible.

the Millenial Career portrait

the Millenial Career portrait

Career Pivots are calculated risks

The fact that you may have been putting off a career pivot is a sign that you view it as something you might fail at. This is a cycle that is vicious and a mindset that will not end in you reaching your ultimate goal.

Career pivots are calculated risks, in a sense that before diving in to any decision, you must first put in work and due diligence in planning it before executing anything.

By planning and mapping out your next steps, you will be able to reduce anxiety, keep track of progress, manage expectations, and distinguish when you need an outsider’s help.


Career coaches are one of your best bets for a successful career pivot. Not only do they guide you during each step, they have networks you can tap, and you can hold someone accountable for you.

Do you think any of the successful career pivoters got to where they are all on their own? Some of them may have advisers, spoke to consultants, or even confided to someone for a different perspective or professional insight.

Some key traits worth holding on to during the process are flexibility, openness, and realistic.

But what if I fail?

The fear of failure is definitely something that takes someone aback during the very early stages of a career pivot, and it doesn’t really go away anytime soon. But if there’s something that your years have taught you, it’s that failure is the best way to gain knowledge in the learning process.

However, first and foremost, you have to acknowledge what failure means to you, just as you have to define what success means to you.

How do you conclude something as a failure? Is it about not meeting your expectations? Is it about not having customers in the first few months of your business? Is it the lack of conversion? Or not being able to pick up a skill as fast as you’d like?

I don’t want to sound like a motivational poster here, but think of a career pivot as an experiment to which error along the way is not an indication of failure, but an indicator of what works and what does not.  The only time an experiment becomes a failure is when one stops trying to reach the end objective. You either find a way, or make one.

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There are people depending on me financially

Forbes listed a few metrics that you can consider as financial decision-making criteria during a career pivot.

  • Money saved (Pivot runway): Have at least 6 months worth of savings to see you through

  • Money earned (When my side hustle earns X dollars or more): Analyze the likelihood that your side job can also generate income

  • Stay until OBO (Or Better Offer): Only change if given a more enticing offer

  • 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 are anticipating any incoming receivable, it may convince you to stay for a certain amount of time.

  • Outside funding approved (When I get a bank or family loan, or venture capital or angeI funding): Do you really need one? Or maybe you might along the way?

This will help guide you, if you think that financially, the risk of a career move is high.

Ready to make your own career pivot happen?

We’d love to hear where you’d like to head next in your career. Talk to us and we’ll prepare the best solutions fit for your case.

Petra ZinkimpaCCCt