What If There’s Another Version of Success?

Ambition is literally defined by our desire for success, power and wealth.

But what if those aren’t the things you’re most interested in having more of?

In this episode, we’re talking about a different place to put all that ambition, why I’ve stopped treating business growth as the obvious place for mine, and what happens when you start asking what’s actually worthy of your ambition.

Welcome back to the Paid & Peaceful series, where I’m spending the next few weeks questioning some of the things we’ve been taught to want from our businesses. 

So far we’ve talked about defining enough and what I call Comfy Money. Today, we’re getting into ambition, because once you stop automatically chasing more, there’s a pretty obvious question that comes next: What the hell are you ambitious for instead

I’m an ambitious person. I like achieving things, challenging myself and having something to work toward. That hasn’t changed. What has changed is how I’m pursuing that ambition. 

Because ambition, especially in business, almost always means MORE. More money, more clients, more revenue, more recognition, more influence, more growth. It’s literally baked into the definition: ambition is the desire for success, power, wealth or some other major achievement.

And I still want more. I just want more of the things that are impossible to quantify and have very little to do with power or wealth in the traditional sense. 

I want more time doing things I genuinely enjoy. More rest, creativity, fun and adventure. More time with the people I love and more energy to actually be present with them. I want work that challenges me without consuming me. I want to read 100+ books a year. I want to grow watermelons from seeds and dry lavender from my garden. I have a list of places I want to hike, swim and kayak.

I want a comfy life that aligns with my values and feels interesting, satisfying and well lived.

Basically, now I’m ambitious about having a life well lived, and I definitely didn’t think about ambition that way.

The Ambition I Thought I Was Supposed to Have

When I was younger, success felt much more like checking boxes. Get the career. Make the money. Get married. Buy the house. Have the kids. Do the things you’re supposed to do.

Weirdly, I didn’t even consider myself particularly ambitious back then. I was a drama club kid without some grand plan for what I was going to do with my life. I wasn’t walking around at 17 with a five-year plan.

As I got further into my career and then entrepreneurship, I absorbed a very particular version of ambition because entrepreneurship LOVES more.

If you make $100,000, why aren’t you making $250,000? If you’re making $250,000, why not $500,000? Why not seven figures? Why aren’t you scaling? Why aren’t you hiring? Why aren’t you building a bigger audience? Why aren’t you marketing more? Why aren’t you turning your expertise into six different revenue streams?

There’s always another level, like it’s a video game. 

For women particularly, there’s another complicated layer here. I came up during an era when there was a very real and necessary message that women could go after things generations before us had been denied. Money, careers, power, independence, success and leadership.

Somewhere along the way, I internalized another message: if I have the opportunity to do all of these things, maybe I should. Like somehow I was letting feminism down if I didn’t girlboss it up and do it all.

I’ve come to realize something that feels ridiculously obvious now: having choices was the point. Not choosing everything.

Having the opportunity to build a big business doesn’t mean I have to. Being able to make more money doesn’t mean I’m obligated to maximize my income. Being able to work incredibly hard doesn’t mean I should.

The Seven-Figure Plan I Absolutely Didn’t Want

Years ago, when I was running my agency, I mapped out a plan to get it to seven figures. Not vaguely. I actually worked the fucking thing out. What would we need to sell? What would the business need to look like? What would need to change?

Pretty quickly, I realized getting there would require a lot more hiring, which meant a lot more management. I looked at the business I would need to build to achieve this supposedly impressive goal and thought, I don’t want that job.

Could I have done it? Probably. Did some part of me want to prove that I could? Absolutely.

That’s something I’ve had to untangle in my relationship with ambition because there’s a huge difference between: I want this, and I want to prove I can do this.

Now I look at this as desire-driven ambition and proving-driven ambition. Desire-driven ambition says, I genuinely want to have, do, create, experience or achieve this thing. Proving-driven ambition says, I want what achieving this thing will prove about me.

Maybe it proves I’m successful. Smart. Disciplined. Capable. Good enough. Maybe it proves I can handle more than everyone else.

Let me tell you, I’ve spent some time in that second category.

Look How Much I Can Handle

There was a month early in my business when I billed 182 client hours. One hundred and eighty-two BILLABLE hours, which obviously doesn’t include all the other hours involved in actually running a business.

Do you know what I was thinking? About the money. 

Ma’am. Calm the fuck down. You can make money next month too.

But at the time, there was real pride in it. Look how hard I can work. Look how much money I can make. Look how much I can handle.

I’ve always prided myself on being a hard worker and being able to do things other people can’t handle. And that pride is real. I’m not going to rewrite history and pretend there wasn’t a payoff. There absolutely was.

The problem is that the feeling doesn’t last.

You prove you can handle one ridiculous thing, and then you need another thing to prove. You hit the money goal, and there’s another money goal. You get the promotion, and there’s another promotion. You built the business, and now you’re supposed to scale it. 

There’s no finish line.

If I could go back and talk to the version of me billing 182 client hours in a month, I would tell her exactly that: There is no finish line, so sit down already.

When Your Fucks Get Uninstalled

A lot of this started shifting for me in my 40s. Part of it was getting older and simply caring a whole lot less about what other people thought.

My fucks were slowly being uninstalled.

But some of it came from losing people in my life. Death has a pretty incredible way of cutting through a lot of bullshit. It made me look at some of the things I was chasing and think, NOPE, Go live your life.

I realized I didn’t want to spend my entire life earning the right to enjoy it.

For years, I treated the good stuff like something I earned through work. Work hard enough and then take the vacation. Make enough money and then rest. Get everything done and then go outside. (I know so many of you are feeling personally called out right now!) 

There’s always something else you could be doing. Another client you could take. Another marketing strategy you could try. Another opportunity you could say yes to. Another dollar you could make.

Learning how not to hustle has genuinely been a journey for me because even after I consciously decided I didn’t want to operate that way anymore, the internal chatter was still there telling me, You should be doing more.

I want to acknowledge that even being able to question hustle comes with privilege.

There have absolutely been times in my life when I had to work more because I needed the money. And there are millions of people working multiple jobs, taking every shift or saying yes to work they don’t want because the alternative is not paying rent or putting food on the table.

That’s not hustle culture. That’s survival.

Hustle Culture Sold Us a Crappy Promise

Eventually, I started questioning the entire premise of hustle culture. Because what exactly is the promise here?

Work hard. Keep pushing. Do more. Make yourself more productive. And eventually, all of that effort will be rewarded.

Except we have plenty of evidence that it doesn’t actually work that way. 

The International Labour Organization has examined working hours worldwide and found that longer hours are generally associated with lower productivity per unit of labour, while shorter hours are associated with higher productivity. They’ve also found that working longer hours than you actually want has a negative effect on work-life balance.

When I joke about my 182 billable-hour month now, I can laugh at myself and say, “Ma’am, sit the fuck down.” But there’s something much more serious underneath it.

We’ve all spent decades treating the willingness to sacrifice our health and well-being for work as evidence that we’re ambitious.

And for what? Because the other part of hustle culture’s promise, that if you work hard enough, you’ll succeed, isn’t true either.

Hard work matters. Obviously. I’ve been in business for more than 20 years, and I'm not going to pretend I got here without putting in the effort. 

But hard work is not a guarantee of reward.

Statistics Canada has tracked intergenerational income mobility, and their research found that where your parents sit in the income distribution has become more, not less, connected to where you end up. Among the Canadians they studied who were born into the bottom 20% of family incomes, the likelihood of remaining in the bottom 20% as adults actually increased across generations.

We aren't all starting from the same place, which matters when we talk about ambition, because we tend to look at the people who end up with the most money, power, or conventional success and assume they must have wanted it more or worked harder to get there.

Ambition doesn't exist in a vacuum.

It’s a whole lot easier to take a big risk when you have a safety net. It’s easier to work ridiculous hours when someone else is taking care of your home or your kids. It’s easier to start a business when you have access to money, connections or a partner with a steady income and benefits. And it’s easier to recover when something goes sideways when one bad decision isn’t going to completely screw up your life.

None of that means someone didn't work incredibly hard for what they have. Both things can be true. You can work your ass off AND have advantages that make it more likely that all of that work will actually pay off.

The problem is when we look at the outcome and turn it into evidence of someone’s ambition or work ethic. They made millions, so they must have worked harder. They built a huge company, so they must have wanted it more. And if you haven't achieved those things? Well, maybe you just weren't ambitious enough.

That's where hustle culture goes from annoying to actively harmful for me, as ambition isn't a meritocracy.

Your ambition doesn’t need to be measured by how much of yourself you’re willing to sacrifice to prove that you work hard.

I’m Still Ambitious, But I’ve Got a New Scoreboard

These days, I’m much more interested in measures around my life.

How much control do I have over my time? Am I doing work I genuinely enjoy? Do I find my work interesting and challenging? Do I have energy left when I’m finished working? Can I take care of my body and my brain? Am I getting enough actual rest? Do I have room for creativity that doesn’t need to become content or make money? Am I having fun? Am I having adventures? Am I reading books? Am I getting outside? Am I going to the places I want to hike, swim and kayak? Are my watermelons growing?

These things don’t show up on a business dashboard. Nobody is going to put me on a stage because I successfully grew a watermelon from seed. But these things matter enormously to me.

I’m still ambitious as hell. I’ve just moved the scoreboard.

I still want MORE. I want more of the things capitalism is downright terrible at measuring. Increasingly, I care more about whether my life is expanding than whether my business is.

Every Yes Takes Up Space

There’s another piece of this that’s become much more important to me: every ounce of ambition costs something, and the cost isn’t just time.

This is where Space in the Staying Solo framework comes in. When we’re deciding what our business can do, we can’t just look at the available hours on the calendar. Something may only require three hours of my time and still completely flatten me.

Things cost us energy. They cost emotional capacity. They cost sensory capacity. They require rest and recovery.

Now, when I’m deciding whether I want to do something, I’m much more interested in the trade-off. Sure, I could say yes.

But what am I saying no to by saying yes to this?

That’s been a huge shift for me. I say no a lot more now, and I’ve had to get over the FOMO that comes with that. I say no to marketing opportunities. I say no to clients who aren’t an ideal fit. I say no to things that younger me probably would have looked at and thought, But what if this leads somewhere?

I’m fiercely protective of my capacity. I need that capacity to take care of myself, my body, my brain and my well-being. 

I can’t be equally ambitious about everything. If I pour all of my ambition, energy, curiosity and drive into my business, what exactly is left for everything else? Like, yes, I need to make money to pay the bills, but after that, some of that capacity needs to be reserved for my life. 

What’s Worthy of Your Ambition?

I’m not going to tell you to stop wanting more.

Maybe you genuinely want to build a seven-figure business. Go for it. Maybe you want employees. Maybe you want a huge platform. Maybe you want to become incredibly wealthy. Maybe you want to build something and sell it. Those aren’t inherently bad ambitions, and staying small isn’t inherently more virtuous.

And please don’t do something because you don’t want to ‘play small’; staying strategically small can be the best choice for you. 

Before you point years of your life toward something, interrogate the want.

Ask questions like: 

• Would I still want this if nobody knew I achieved it? 
• What do I believe achieving this will prove about me? 
• What do I think this will give me? 
• Do I actually want the reality required to create this outcome? 
• Who taught me that I should want this? 
• What am I willing to trade for it?

If you’re listening to this and realizing you’re not entirely sure why you’re chasing some of the things you’re chasing, you don’t need to burn your business down.

But maybe it’s time to reassess. Not just your next goal, but the overall direction you’re heading.

Where’s all of this taking me? Is my business giving me more of what I actually want from my life? Is my life becoming more comfortable, interesting, creative, adventurous and spacious? Am I getting more choice? Or am I simply following the next logical step because that’s what ambitious business owners are supposed to do?

That’s a big part of what we’re going to be doing inside the next round of the Paid & Peaceful Mastermind. You’ll look at what you’ve already built and decide what you actually want from it now, asking yourself: what deserves your capacity, where do you need to make more money or what needs to change so the business you’re running actually supports the life you’re trying to live?

Because you don’t need to become less ambitious. You need to decide what’s worthy of your ambition, and build from there.

Enrollment for the next round of Paid & Peaceful is open now, and there are a limited number of spots available. If this is the kind of business you want to be building, head to the link in the show notes to check out all the details and book your consult with me.

The consult is your chance to ask questions, talk through where you are and what you want next, and for us to make sure the mastermind is the right fit for you.

Now, go book that consult. I’d love to talk to you.