How to Know When It's Time to Make Career Changes with Michael Barber — Part 2

November 26, 2025 00:08:31
How to Know When It's Time to Make Career Changes with Michael Barber — Part 2
Time Billionaires: Mindset and Time Management for Work & Life
How to Know When It's Time to Make Career Changes with Michael Barber — Part 2

Nov 26 2025 | 00:08:31

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Show Notes

In Part 2 of this Time Billionaires episode, Rebecca continues her conversation with Michael Barber, Chief Marketing Officer at StarTech, diving deeper into career decision-making and the courage required for growth. Michael introduces his powerful "mirror test" for decision-making, asking yourself whether your current choices reflect what you want to see in the mirror, both literally and metaphorically.

 

This framework helps him evaluate everything from daily priorities to major life decisions, ensuring his actions align with his desired outcomes. The conversation explores Michael's unconventional career path of spending only 2-4 years at each position, a strategy that was unusual before 2010 but has accelerated his growth through diverse experiences across different industries and teams.

 

He emphasizes that discomfort is the price of growth and encourages embracing uncomfortable decisions rather than avoiding them. Michael shares his personal framework for knowing when it's time to make a career change: when he stops sleeping well. He explains how physical and behavioral indicators can signal when you're not doing what you want to do or feel you're running out of time for what matters most.

 

Timestamps:

- The mirror test: Aligning decisions with desired outcomes – 0:35

- Opportunity costs in personal life and micro-moment decisions – 1:45

- Michael's unconventional career strategy of short sprints – 3:59

- Why being uncomfortable accelerates growth opportunities – 5:30

- How to know when it's time for a career change – 6:29

- Using sleep as a gut-check indicator for life decisions – 7:15

- The "best version of yourself" framework for relationships and jobs – 8:05

 

Connect with Michael Barber:

LinkedIn: https://www.linkedin.com/in/michaeljamesbarber/

 

For more insights on turning hidden minutes into your greatest asset, connect with Rebecca and follow the podcast on LinkedIn!

Time Billionaires on LinkedIn: https://www.linkedin.com/company/time-billionaires-pod

Rebecca: https://www.linkedin.com/in/rebeccashaddix/

 

And if you love the show, subscribe to follow the show!

 

Shout-out to Graham Duncan from East Rock Capital for the "Time Billionaires" concept that inspired our show name - originally shared on The Tim Ferriss Show.

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Episode Transcript

[00:00:00] Speaker A: We have to make those decisions and the quicker we make them, the quicker we move on to the next thing. Being uncomfortable in those moments allows you for those big growth opportunities. So what I would say is when you feel those moments of questioning yourself, what's the thing that you're not doing? Either the things you want to do or you feel like you're running out of time to do the things you want to do. [00:00:35] Speaker B: This is a two part episode. If you want to check out the first part, listen to the previous episode of Time Billionaires. Yeah, we talk about opportunity cost a lot with business with do I go get an MBA or not? There's an opportunity cost to that. And I think a lot of the personal opportunity costs same thing with micro moments are really hard to quantify because it doesn't feel like you're giving up a lot of creative energy to, to take on more of the laundry, cleaning, cooking, shopping, whatever it is, and realizing that it's not indulgent to outsource grocery delivery, etc. Things that don't become richer because you're the one touching them, I think is a really important concept of having the energy for really investing in your micro legacies more thoughtfully. [00:01:17] Speaker A: Yeah, absolutely. I think you have to decide what are the priorities to you and does your, your situation allow you to prioritize certain things and make decisions within both your professional and personal time as to what you're going to action and what you're not going to action. And so I often try and do this. The expression I use myself is put the mirror in front of you and are the decisions that you are making going to reflect what you want to see in the mirror? Both from a physical perspective, but also an analogous perspective as well from an analogy perspective. And I do this to friends as well. Any moment that I start complaining about something or I hear a complaint from a friend about they're not doing this or they're not, you know, this isn't happening in their lives. I'm often like, hey, and I do this to myself as well. Like let's put a mirror in front of me and am I making the decisions? Am I doing the things that actually create the reflection that I'm looking for in the output or, or look that I'm looking for. And I think that's a really great way to think about, you know, for coming back to something to we just discussed around the 3D is that's a really good way to decide like what am I actually going to do outside of 8 to 5, what am I actually not going to do outside of 8 to 5 or what am I going to delegate? Whether that is grocery shopping or going to get my nails done or deciding that today I'm going to have a sweet treat that, you know, costs, you know, $10 to go get like a cupcake or something. Right. We have to make those decisions and the quicker we make them, the quicker we move on to the next thing. And I think that time depth can become such a challenge, whether it is, you know, happening in your 8 to 5 or in your, you know, outside in your personal hours and personal life too. [00:03:05] Speaker B: Yeah, it's true. Time researchers use the definition of work to measure how much leisure time we have now versus before. And they define work as anything that you couldn't delegate to somebody else without it losing its intent. So I couldn't delegate going to a concert because then I don't go to the concert. But you could delegate things that you don't enjoy that have an output that you want in that same way. [00:03:29] Speaker A: Yeah, couldn't agree more. [00:03:32] Speaker B: Yeah, I love the way you think about that in terms of the. That true opportunity cost, the trade off that you have. I'm curious, is there something that you wish you knew about time management at the start of your career or earlier in life? [00:03:45] Speaker A: This is such a great question because it's sort of like a what if and almost like a regret scenario, if you will. I will say this. I'm going to sort of re. I'm going to reframe this question in a little bit of a different way. I often was asked many, many times in your career. If you ever, if you go look at my resume or if you go check out my LinkedIn, you will see that I have spent usually on average two to four years in any given position, which if you think in the grand scheme of things, of a career arc, you know, let's say before 2010, those were pretty short sprints. Now I think it's more normal that people are spending less time at organizations. But one of the things that I am glad I did and I would, and I say to anyone I get the chance to interview or any, if a friend calls me or a fellow marketer calls me or someone that wants some professional advice about leaving somewhere is that for me, I am glad I made the decision to go to new places for a number of very specific reasons that include getting opportunity, getting exposure faster, getting the chance to get my feet wet or my hands dirty, however you want to apply that expression in different industries, in different places, with different groups of people with different types of projects. And so if I had the chance, I would go back and reaffirm the decision to do that. Because early in my career I was very concerned that in the first 10 years of my professional life, I'd been at almost four agencies at that point. But I'm glad I did. And I would tell that to anybody that if you're thinking about, is the grass greener, you have to go figure that out. Nobody's going to answer that for you. And there are times where it is and there's times where it will not be, but you have to go make those leaps. If you want to move your career in really interesting ways, whether that means to be able to do different types of things or to move yourself up the career ladder, There are choices that have to be made. Those are tough choices. Lean into them. They're not going to feel good. That is the point. That is the, you know, being uncomfortable in those moments allows you for those big growth opportunities. And so rather than saying, if I'm, if I am, if I regret any decisions around sort of time and the impacts around my career, I would say I'm. I would reflect back to my, my younger self. Hey, go make those, like, uncomfortable decisions about taking a chance and moving your career where you want it to go early and faster than you thought it probably should have been. [00:06:21] Speaker B: How do you know when it's the right time to do that? [00:06:25] Speaker A: There's a lot of, so there's a lot of probably correct and incorrect answers to this question. I'll tell you the one that I've often fallen back on, and that is, am I sleeping at night? For me, that is, that's my gut, My gut is sleep. I. I've said somebody, people have often said, like, just trust your gut instinct. And I'm like, I have stomach day problems every single day. I don't even know how to trust my gut instinct. So. But what I realized is when I am not sleeping, that's my context, my framework for like, am I in the right place? Doing the right thing is for me, it's sleeping. For other people, it's going to be very different. So what I would say is, when you feel those moments of questioning yourself, what's the thing that, you know, for me, it's what keeps you up at night, right? But there's, there's going to be things that either they are behaviors or nuances, they could be like physical tics or traits that occur when you know you're not doing either the things you want to do or you feel like you're running out of time to do the things you want to do when you start to feel that it's time to go. [00:07:38] Speaker B: That's interesting. Yeah. There's two things that stand out to me about that. I have anxiety, so my instincts are often not the thing that you follow. But you gave it a filter. Your advice there actually reminds me of advice I give to people about romantic relationships and. And partners. And I think it applies to friendships too. Does this person, job, friend make you the best version of yourself? Because I think the question of do they make you happy? Is really tough to answer and a lot of things make you happy some of the time and are not good for you long term. But if this relationship, job, person is stretching you to be the best version of yourself, that's a good fit. Not happy. [00:08:16] Speaker A: Yeah. Such a good framework to think about it through to. Such a good one.

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