Jun 24, 2026 · 40 min · 11 segments
Is career success measured by moving up or moving forward? Cliff Maxwell, co-founder and CEO of Vocation, explores the difference between career progression and career progress, why fulfillment…
Cliff MaxwellGuest
Rishad TobaccowalaHostWell, we're very excited to have you on the show because, like you, we are a big believer that work is changing, and work is obviously very central to the human condition.
In addition to income, it gives us identity and purpose and growth and meaning and a whole bunch of other things.
And- You've obviously spent a lot of time, and now you've innovated a great deal sort of around it.
Um, and one of your central beliefs is there is a big difference between career progression and career progress.
So can you enlighten us about the difference between the two and why we should care?

When we say career progression, we often think of the career ladder, the idea that I need to continually be moving up and doing something that impresses my friends or my family or pays me additional dollars every time I move forward, and we get the sense that if we're not moving up or progressing in that way, then, then we're going backwards or we're not making the, the strides that we need to.

And certainly for someone like myself, who's been a fairly ambitious person, right, and wanted to do big and important things, it comes with a, a large set of expectations around what I should be doing or with this degree that I have, what types of roles I should be considering, because you start to feel like if I'm not progressing along the ways that I've prepared for or invested time and energy in against, then something must be wrong.

And I felt that pressure a lot earlier in my career, feeling like I had to do the thing that was expected or that was consistent with what a ambitious person should be doing and at a pay rate they should be getting paid.

But the difference between that-- Uh, oh, sorry, the second, the second element of, of progression is often what a company wants.

A company wants an employee to start at the bottom and work their way to the top, uh, because a company wants to continue to develop talent as they should.

And so we have in our minds this notion that upwards is the only, only, um, direction for careers.

Progress can be upwards, but it can also just be a different direction or a different field or a sidestep or something else entirely.

What we mean by progress is that as you live your life and as you engage with your career, things happen, life happens, context changes, jobs change.

And so what you want and what you need in a particular context is ultimately a function of what's happening in your life and in your workforce.

So for somebody who is severely burnt out, who fundamentally likes what they do, but just it's not sustainable anymore, right? Progress is about finding something that's in that realm, but in a more sustainable way.

And so it might not be come with a, with a, a bigger paycheck, it might not come with a new title, but for their own sanity and also for them to be able to own their work and to do well and to engage in the things that they know they can do well, progress is all about regaining control of their time and priorities, and that's great.

For somebody else, progress might be something like, you know, I-- my, my job has shifted so much over the last few, few months or years.

I'm not really doing the stuff that I know that I'm uniquely capable of doing.

The skills that I hold dear and that I feel like I'm really good at, my job's not offering it anymore.

And so I need to find an opportunity where I can really, uh, sharpen and do the things that I, I can do well and add the value that I wanna be adding.
Well, we're very excited to have you on the show because, like you, we are a big believer that work is changing, and work is obviously very central to the human condition.
In addition to income, it gives us identity and purpose and growth and meaning and a whole bunch of other things.
And- You've obviously spent a lot of time, and now you've innovated a great deal sort of around it.
Um, and one of your central beliefs is there is a big difference between career progression and career progress.
So can you enlighten us about the difference between the two and why we should care?

When we say career progression, we often think of the career ladder, the idea that I need to continually be moving up and doing something that impresses my friends or my family or pays me additional dollars every time I move forward, and we get the sense that if we're not moving up or progressing in that way, then, then we're going backwards or we're not making the, the strides that we need to.

And certainly for someone like myself, who's been a fairly ambitious person, right, and wanted to do big and important things, it comes with a, a large set of expectations around what I should be doing or with this degree that I have, what types of roles I should be considering, because you start to feel like if I'm not progressing along the ways that I've prepared for or invested time and energy in against, then something must be wrong.

And I felt that pressure a lot earlier in my career, feeling like I had to do the thing that was expected or that was consistent with what a ambitious person should be doing and at a pay rate they should be getting paid.

But the difference between that-- Uh, oh, sorry, the second, the second element of, of progression is often what a company wants.

A company wants an employee to start at the bottom and work their way to the top, uh, because a company wants to continue to develop talent as they should.

And so we have in our minds this notion that upwards is the only, only, um, direction for careers.

Progress can be upwards, but it can also just be a different direction or a different field or a sidestep or something else entirely.

What we mean by progress is that as you live your life and as you engage with your career, things happen, life happens, context changes, jobs change.

And so what you want and what you need in a particular context is ultimately a function of what's happening in your life and in your workforce.

So for somebody who is severely burnt out, who fundamentally likes what they do, but just it's not sustainable anymore, right? Progress is about finding something that's in that realm, but in a more sustainable way.

And so it might not be come with a, with a, a bigger paycheck, it might not come with a new title, but for their own sanity and also for them to be able to own their work and to do well and to engage in the things that they know they can do well, progress is all about regaining control of their time and priorities, and that's great.

For somebody else, progress might be something like, you know, I-- my, my job has shifted so much over the last few, few months or years.

I'm not really doing the stuff that I know that I'm uniquely capable of doing.

The skills that I hold dear and that I feel like I'm really good at, my job's not offering it anymore.

And so I need to find an opportunity where I can really, uh, sharpen and do the things that I, I can do well and add the value that I wanna be adding.
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