B084: When is it best to make a career pivot?

By October 18, 2019The Simplifiers Podcast

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Are you contemplating a big pivot in your career? We received a listener voicemail from Audrey at Timeless Beginnings Wedding Coordinators in San Antonio, Texas, asking us just that… when is it best to make a career pivot?

Whether that’s changing your pricing strategy, offering different products or services, launching a new business or exiting one, let’s talk about it!

Thank you Audrey for tuning in to the podcast and submitting your question! So, if you’re feeling like a big change is afoot, you’ve hit a plateau, and want to know when is the best time to make a career pivot, let’s break it all down.

There are three indicators you need to consider:

  • financial milestones
  • looming deadlines
  • … and a good ol’ fashioned gut check.

Here’s how to make a career pivot at precisely the right time – look for these key indicators:

1. Financial milestones

You might find that setting (and subsequently hitting) a financial goal will be the right trigger for you to make a big change or pivot in your career. For example, that might look like…

  1. Saving enough money to cover at least 6 months of expenses as an emergency fund (some people call that a “pivot runway”)
  2. When you receive funding (whether it’s a grant or a loan or angel funding) and you can purchase the necessary items to launch this new venture 
  3. Hitting a revenue target with your newly launched business so you make the leap and quit your full-time job
  4. When you receive a job offer that is too good to pass up – either taking you away from entrepreneurship altogether or leading you onwards to your next opportunity
  5. Or when your business isn’t generating the income you hoped and it’s headed in a downward spiral beyond repair…

Whatever it is, there might be one or two financial milestones that you’ll need to set so you’re super clear on when you’re going to pivot and enable you to move FAST.

2. Looming deadlines

I don’t know about you, but when I set a deadline and then announce it to the world, it all of a sudden becomes REAL, really quick. If you’re thinking about exiting your business or shifting your focus in a significant way, maybe setting a specific date in your calendar could be just the thing to propel you forward? Here are a few deadline-based factors that could help you trigger a pivot…

  1. When does your busy season typically end? Set a date in your calendar for that point and make a promise to make the big change on that exact date (whether it’s to your pricing or your product offering… or even stop accepting clients past that point).
  2. When is the next big project going to be completed? Once that project is done, can you make the leap after that, so you aren’t leaving anyone in the lurch beforehand?
  3. Set exact dates for a sabbatical – let’s say you want to take a week, a month or even a year(!!!) off to explore – set the date, start saving the money and then work towards making this a reality. I know, I know… it sounds so simple, but what if it actually is??
  4. Let’s say you want to move to a different city (or country!) Set a date, buy the plane tickets and work backwards from there… there’s nothing more motivating than that, trust me, I know!

3. Gut check time

Reality is, your Intuition knows a heckuva lot more than you give her credit for. Whether your health is starting to decline from burnout or you’re getting red flag feelings about something that seems peculiar, you know that it might be time to make a change. Raise your hand if you’ve ever said or thought this…


  • I gave it my all and it just wasn’t enough – I tried everything I could to make it better!
  • I simply can’t live like this any longer – something has got to change because I’m feeling miserable
  • Something deep down inside me is calling me towards this thing… 
  • … or something is telling me quite the opposite, “run! run away from that!!”

Listen to her… always listen and dig deeper into what she’s trying to tell you.

One final whisper


Change is scary. Trust me, I know. And while I used to subscribe to the theory that “change is the only constant in life,” I’m starting to change my tune a bit due to a little more maturity and time on this planet. Instead of change being the only constant, I’ve decided to shift my perspective and resonate much deeper with this thought…

“I’m the only constant in *my* life.”

At the risk of sounding a bit egotistical in saying that, hear me out. I’m sure you’ve heard people mention, “whatever you focus on, you attract,” right? So, instead of focusing on the change in your life, what if you slightly shift things and for once, focus on you?

What is it that YOU want in the next chapter of your life? Like Danielle LaPorte says, “how do you want to feel? What are your Core Desired Feelings?” For many of us, we’ve dampened that light for way too many years, to succumb to what other people want or need for sooooo long that we forgot to focus on what we want and need; what lights us up.

So, as you contemplate what lies ahead, set a 7-minute timer and take a moment to journal out what you really, really want your life and career to look like. 

Ask yourself…

  • What would an ideal workday look like?
  • How much vacation time do you want to take?
  • What kind of tasks or projects would you really enjoy working on?
  • How much money do you want to make?
  • What kind of a lifestyle change would you need to make, in order to create this vision into a reality?
  • Do you need to move to a new neighborhood or a new city?
  • Closer (or further away!) from your family?
  • What would bring the joy back into your life?
  • What would end the suffering?
  • What’s it going to take to make this big shift? Time? Money? Support from your friends, family, colleagues or otherwise?
  • … and when are you going to do it? Set a date, make it happen, work backwards to create a plan and then #dothething.

Despite the fear.

Or anxiety.

Or the constant worrying.

All of those things start to quiet down once you’ve acknowledged a change needs to happen, process the big emotions that come with that pivot and then create an imperfect plan to make daily progress towards it. Don’t overthink it… just clarify, feel it, and then, take action.


You can do this, I believe in you.

It’s time to SIMPLIFY.

If this thought of the day inspired you…

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Thank you!

Show credits: Suzen Marie, our Podcast Editor. Jeffrey Lynn, our Video Editor. Lyden Yardley, our Show Notes Editor, and Manminder Athwal, our Blogger. Aubri Nowowiejski, Chris Justice and George Mills, our advisory board. And I’m your host, Mary Baird-Wilcock. Thank you so much for joining us.

As always friends, keep things simple.

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