Let's talk about money. Not in a "here are five revenue streams" kind of way. More in a "how do you keep the lights on while you're quietly rebuilding the entire house" kind of way.
Because that's the part nobody talks about when they tell the pivot story. They tell you about the clarity. The moment they knew. The big leap. They don't tell you about the Tuesday morning when the credit card bill comes in and you're thinking, okay, but I still need to eat while I'm becoming this new version of myself.
This isn't a story about burning it all down. It's about the overlap, where the old work funds the new work, and you're trying very hard not to collapse in the middle.
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In this episode
Why the headline version of a pivot story is too small for what a pivot actually is
How I'd been circling this pivot for a decade
"Right thing, wrong time, wrong thing," the mantra I keep coming back to
What burnout recovery looks like when you still need to make money
Why you don't blow up the thing that pays you
Three rules for pivoting without a financial freefall
The real story behind a career pivot
There's a headline version of this story, and then there's the real one. The headline version goes like this: woman hits forty, goes through a divorce, burns out, reinvents herself.
It's not wrong. But it's too small. It takes something that's been building quietly for over a decade and squeezes it into a single before-and-after. Like nothing was happening before the dramatic part started.
I'm a planner to the core of my being. One-year, five-year, ten-year plans since I was about fifteen. So a few years into building my event business, my brain was already looking ahead. I didn't have the language for it yet, but I knew the work I was doing wasn't the ceiling.
So I started exploring. I built out a whole separate website at one point. Did a branding shoot. I was developing a course teaching people how to plan styled shoots to build their businesses. I went all the way down the path, as far as felt right. And then I stopped and checked in. The truth was, I still really, really loved events. I had so much work coming in, and splitting my focus between building a course and running a full event business wasn't the right time.
I'm a big believer in "right thing, wrong time, wrong thing." It's simple, but it's been one of the most clarifying mantras I live by. So I set it down. Not because the idea was wrong. Because the timing was wrong.
But I didn't stop paying attention. I kept leaving breadcrumbs for myself. I started saying yes to speaking, because I was curious what it felt like to put my thinking into a room instead of just my execution. I shifted toward more creative direction. I brought more of the human element back into my events, the why behind the gathering, not just the how. I felt a bigger pull toward community. And then I built Camp Rover, and learned I could design a gathering from the ground up. Not plan someone else's vision. Design my own.
So by the time the divorce happened and the burnout hit, it wasn't a sudden reinvention. The divorce and the burnout didn't cause the pivot. They cleared the path for something that was already in motion.
You can't iterate if you're broke
Here's the thing about iteration. You can't iterate if you're broke. You can get a loan, funding, self-fund. But I'm talking about a business that's already working. A business you're shifting. Consider that my caveat.
This is where most people lose the plot with pivot stories. They make it sound like you wake up one day, decide to change everything, and the universe rearranges itself around your new vision. That's not how it works.
How it actually works is: you keep doing the work that pays the bills, while you build the work that will pay the bills eventually, and hopefully then some. The holiday. The retirement fund. And you try very hard not to burn out in the overlap.
I don't want to breeze past this part. You don't just decide you're no longer burnt out. And you can't rest your way out of it. Recovery is more like rebuilding a muscle that's not even firing anymore. It's a lot of ripping and growing. Sometimes you push too far and feel yourself getting close to that edge again, so you learn to back up quickly. You learn what your warning signs are. You learn that the margin between stretching and breaking is narrower than you thought.
If you're in it right now, please don't isolate yourself. Share it with someone. Even one person. You don't have to figure it out alone.
How to keep your current clients while you build something new
I didn't drop my event clients. This year, I still have weddings on my roster. I still have corporate contracts. I'm not stopping being an event planner. I'm shifting away from doing it as my full-time, only thing.
My staff will run more events themselves. My systems will get better so clients are taken care of at a higher level with less of me in every email. When you're this far into a business with a reputation and a roster, you can't just bolt new things on and expect them to work. The infrastructure has to shift too.
But I changed the filter. I stopped saying yes to everything. I started asking: does this client, this event, this project let me do the kind of work I'm moving toward? Does it let me think? Does it let me design? Or is it purely execution?
The events I kept are the ones with a heartbeat. A mission. A reason beyond production. People tell me what a luxury that is. That's not a luxury. That's a positioning decision. Every event I take on is still telling the market who I am.
I'm not going to sugarcoat the overlap. You're running a full event season while writing podcast scripts, building an education offer, designing a new website, updating the branding and figuring out consulting pricing. Some weeks, it's a lot. But it's not a failure. It's not a sign you should have just picked one. It's the transition doing what transitions do. The old work is funding the new work. That's not a problem. That's the plan.
Three rules for pivoting without a financial freefall
First: don't blow up the thing that's paying you. When you get clarity about where you're headed, you want to sprint toward it, and the work you're doing right now starts to feel like an anchor instead of a foundation. Trust me, I know the urge to sell it all, hide in a jungle hut with great wifi for a month, and come back with a whole new business. But that's not anchored in real life. So consider reframing the anchor. It's buying you time. It's funding the transition. The goal is not to escape the old work. The goal is to graduate from it. Intentionally.
Second: shift your language before you shift your revenue. The market can only hire you for what it thinks you do. If your website, your LinkedIn and your conversations still sound like the old version, that's what will keep coming in. You don't need to rebrand overnight, but you do need to start putting the new language into rooms. I took little taglines and tried them out at networking events, checking how they landed. Instead of "I plan events," it became "I help people design gatherings that actually work, and I consult with business owners who are navigating transitions like the one I'm in." All of my launches this year have been quiet launches. Don't let shiny launches that have nothing to do with your business, your industry or your timeline make you feel behind in your own lane. Talk about what you're thinking about, not just what you're doing. That's building the bridge while you're walking across it.
Third: give yourself a timeline, not a deadline. A deadline says: by this date, the old business is gone and the new one is running. That's pressure that doesn't help. A timeline says: over the next twelve to eighteen months, I'm going to gradually shift the ratio. More upstream work. Fewer purely operational clients. A bit more consulting revenue. A bit less execution revenue. It's not dramatic. But it's sustainable, and sustainable is the whole point. Do your research and map it out, but give yourself room. You have to factor in delays, personally and professionally.
What if the new thing doesn't work?
I think the fear underneath all of this, the one nobody says out loud, is: what if I let go of the work that's paying me, and the new thing doesn't work?
That's a real fear. I've sat with it. And the answer I've come to is this: you don't let go. You build until the new thing earns its place.
That's not a leap of faith. That's architecture.
Key line
The old work doesn't leave because you decided you're done with it. It leaves because something better has grown underneath it. And by the time it does, you're ready. That's architecture.
Reflection question
Look at your business right now: the clients, the projects, the way you spend your hours. What percentage of that work is funding your current life? And what percentage is building toward your next step? If the answer is 100 and 0, what's one thing you could shift this month to start changing that ratio? Not a big leap. Not a rebrand. Just one conversation, one piece of language, one offer, one post.
Timestamps
00:01 Let's talk about money
02:00 The headline version of a pivot story
03:44 Circling this pivot for years
06:05 Right thing, wrong time, wrong thing
11:06 Building Camp Rover
11:46 What the divorce and burnout actually did
13:55 You can't iterate if you're broke
17:11 You can't rest your way out of burnout
21:25 Keeping event clients, changing the filter
29:19 Building the upstream work
31:04 The overlap isn't elegant
32:03 Rule 1: Don't blow up the thing that pays you
33:57 Rule 2: Shift your language before your revenue
37:56 Rule 3: A timeline, not a deadline
38:58 What if the new thing doesn't work?
40:07 Reflection question
FAQ
How do I pivot my business without losing income?
Keep doing the work that pays the bills while you build the work that will pay the bills eventually. Don't blow up the thing that's paying you. Let it fund the transition, and change the filter on what you say yes to.
How long does a business pivot take?
Give yourself a timeline, not a deadline. For me, that's gradually shifting the ratio over twelve to eighteen months: more upstream work, fewer purely operational clients. And factor in delays, personally and professionally.
Do I need to rebrand before I change what I offer?
No. You don't need to rebrand overnight, but you do need to shift your language before your revenue. The market can only hire you for what it thinks you do, so start putting the new language into rooms early.
Can you recover from burnout while still running your business?
You can't rest your way out of it. Recovery is more like rebuilding a muscle that's not firing anymore. Learn your warning signs, learn to back up quickly, and don't isolate yourself. Share it with even one person.
This post is based on Season 1, Episode 8 of Work, By Design, a podcast by Amanda Douglas & Co. about redesigning how you work.
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