How to Make a Massive Pivot… Safely


This story may sound familiar to many people! You have bills, rent/mortgage, and other financial obligations. And that thought alone can be scary because you know the risk of a pivot is high!

But it’s not always feasible to quit what you’re doing to pursue a new business or strategy.

Listen closely for David’s personal story about his own pivot and how he safely did it:

  • How to fund your pivot.
  • What you can do to ‘test’ your pivot idea before taking the plunge.


When you need to make a massive pivot – SAFELY – dip your toe into the water first to remove your risk.

– David Wood


To find out more about Brian, go to and watch the FULL INTERVIEW here. 


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Brian Ondrako: [00:00:00] Probably those, you know, those personal development courses you took probably helped give you the competence, right. To make that leap and ultimately go out and do your career or whatever you want to call it.

David Wood: [00:00:10] Yeah. But also you don’t always have to go cold Turkey. Or you don’t, it’s not always a binary condition.

So I didn’t wake up one morning and say, I’m quitting my job. And I’m just going to have a career as a musician. I just said, I’ll take six months off. Yeah, and I’ll do music now. It ended up expanding into a year and a half of music. And then and I didn’t let go of the actuarial stuff. So I was consulting.

I had quit my job, but I went, I needed money. Right. So I didn’t want to just burn all my savings through in six months. So what I did is I went to my contacts in Australia and I said, I’m available for hire. Do you need a pair of hands? I got really good work. I was 28 years old and I’m getting paid a hundred to $150 an hour.

I remember thinking back then, it was like 25 years ago, 150 bucks an hour to work from home to consult. Amazing. And that funded me my ability to start this new business. I also kept hold of that for at least a year, while I was coaching, because I needed something on the side. The day I stopped with my actuarial clients was a huge day, but I held onto that lifeline for a year until I resigned.

And that was scary, that I felt like I didn’t have too much of a net because what if the business didn’t work. But I thought I could probably go back and beg and get back to it. I had another pivot again. Oh. Also when I moved to Bali, I moved to Bali say five years ago that wasn’t like a permanent life change.

I just said again, what would I do if I could do anything I want for six months? And I went deeper. I said, what if I only had six months to live? I think it’s a great question. And listen, as I, I challenge you each to answer that today, if you had six months to live, what would you do with your time? And my answer at that time was I’d spend more time in Bali.

I love it and I’d missed it and I want to get back. So I went to Bali for just two months. And then while I was there, this might remind you of the task story because I didn’t commit, I just two months. And while I was there, people said, do you live here? And I wanted to see what it would be like to say yes. Like what would it feel like? So I started saying yes, and you know what, it felt pretty good. So I actually, my girlfriend and I ended up breaking up for other reasons. And I came home, sold all of my stuff and got two suitcases and I moved to Bali. So, you know, might look later like, wow, what bold decisions you resigned as an actuary?

And became an entertainer. And then you, you know, you quit and became a coach and then, you know, you move countries. Even when I moved to the States the second time, I didn’t say bye everybody. I’m leaving my girlfriend and my life and I’m moving to the States. I just said, I’m going to travel for two months.

It wasn’t until I got to California the thought occurred to me that I didn’t have to go home ever because I had my wallet. I had my laptop and I just broken up with my girlfriend. The only other thing tying me to Australia was I was paying rent. So I did a deal with my girlfriend. I’ll pay the rent for the next three months.

Then you take over the lease. I’ll come back, we’ll work out, keep my stuff, use my stuff. When I come back, we’ll work out what to do with it. And I didn’t go home. That was my move to the U S. So I’ve actually, accidentally, done a lot of things. And what I hope people can take out of this story is you don’t always have to take that white knuckling decision.

There are often ways that you can dip your toe into the water and see how it feels before you make the plunge.

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