The Baggage Packs Itself
When I left my secure, well-paying job to start my business, I had a few really good months where I felt completely free. I was calling my own shots. I’d done this brave, terrifying thing, and I was riding the high of it. And then, somewhere around the six-month mark, something familiar started to creep back in.
I was rewriting emails seventeen times because “what if somebody judges me?” I was saying yes to things I didn’t want to do because no felt too risky. I had that voice in my head asking who the hell I thought I was, right before I tried to do anything that mattered. None of it had stayed behind at my old job. It had sneakily repacked itself and come along for the ride, because that’s what baggage does.
That’s the whole subject of my conversation with career coach Monika Kunz, founder of The Springboard.
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We think the job was the problem
Here’s the story almost all of us tell ourselves: The job was the problem. The boss was the problem. The culture, the politics, the commute, the meetings that should’ve been emails. We leave to build something of our own, not just to escape all that, of course; we’re building meaning-driven businesses, after all. But leaving all that behind is an added bonus. Or so we think.
A few months in, so many of us are genuinely shocked when the same reflexes are still running the show, except now there’s no boss to blame for any of it.
Monika put it in a way that reframed it for me. These patterns don’t come from the office. Conflict aversion, people-pleasing, the need to over-deliver so nobody’s ever disappointed in you — those are all things we learned in childhood and have carried with us ever since. Those patterns almost never come from a job, but work (especially in highly stressful, less-than-healthy environments) tends to amplify them. So when you leave, you’re not going to magically rid yourself of those patterns.
At one point you’re the leader, you’re managing a huge team. And then you take a leap, you pivot, and all of a sudden you’re a newbie — brand new to this industry, this field, or entrepreneurship.
Which means the thing a lot of us are waiting for — the day the business gets stable enough that these feelings finally quiet down — is never coming, because external stability was never what was driving them. That sounds bleak for about ten seconds, and then it becomes the most freeing thing in the world. If the pattern isn’t about your circumstances, you get to stop trying to fix your circumstances and start working on the actual thing.
The fear lives on the front side of the conversation
Monika told a story about a client of hers, a brilliant high earner with an incredible network, who can land a scary big client without blinking. Her struggle is conflict. Any hard conversation, and she freezes. So Monika does something I love: she has her clients practice doing the scary thing in a situation they know they’re going to be leaving. This makes it a low stakes setting to build the muscle before it counts.
And as Monika says, the fear around conflict sits on the front side of the conversation. All the dread, all the what-if-they-don’t-listen, all the bracing happens before. The actual conversation, the one you’ve been avoiding for two weeks, is almost always the easy part once you’re in it. Monika described the feeling on the other side of a hard conversation done well: I was heard, my need was met, I got what I wanted. Avoidance keeps you from that feeling.
I can express what I need in a respectful, kind way, and we can resolve the issue and actually deepen our relationship.
I know this firsthand because Monika and I have had hard conversations inside our own working relationship. In addition to being a friend and colleague, she’s been my client — I did her brand and her website, and she was in the very first Bold Content Collective cohort — and we’ve worked through the occasional uncomfortable moment together. Every single one deepened the relationship. That’s what avoidance steals from you. When you skip the hard conversation, you also skip the closeness that lives on the other side of it. The relationship just stays shallow, and you never find out it could’ve been more.
When do I get to call myself the owner?
Monika hears a version of this constantly from newer business owners who are reticent to actually call themselves that. She has clients who’ve formed their LLCs, even filed trademarks, who still can’t quite say the word founder out loud. So much of the early work is invisible and unglamorous, and it’s hard to feel like a CEO while you’re googling how to do your own taxes at eleven at night.
We went back and forth on imposter syndrome, but my take is the goal shouldn’t be to get rid of it. I think roughly every woman I’ve ever worked with carries some version of it, and the ones who seem fearless have usually just gotten good at acting alongside it. Monika made a related point I hadn’t considered: the men she coaches feel it too. They’ve often just been trained out of saying it aloud, so the feeling just gets stifled. Naming it comes from bravery and self-awareness.
So the real move here is changing how much imposter syndrome gets to drive. There’s a world of difference between “I feel like an imposter and I’m going to send the email anyway” and “I feel like an imposter so I won’t.” Same feeling, but leading to a completely different business.
Freedom is the wrong word
A lot of people leave their jobs chasing freedom, and then a year in they’re working more, stressing more, and somehow feeling less free than when they had a boss. Monika’s response to this was the sharpest thing in the episode: freedom is too vague a word to build a life around. You have to ask what kind of freedom you’re looking for.
It can mean financial freedom in ten years, which might mean working brutal hours now on purpose, and that can be a perfectly aligned choice. It can mean never having a boss who isn’t you, which is the version Monika picked for this season of her life. It can mean being able to do school pickup, or work from anywhere, or never check email after six. If you don’t name which freedom you’re actually after, you’ll chase a blurry feeling and wonder why you never feel like you’re getting closer to that goal.
So often we think that success means this one thing, and success actually is not usually in that box. Sometimes it’s way outside of the box.
Another layer Monika added that’s so important: the answer isn’t permanent. The freedom that mattered to you in year one may not be the same freedom that matters in year four. She finds that her longest-term clients are business owners precisely because this question needs revisiting. You don’t set the definition once and coast. You check it, the way I check in with a coach every single year of my business, asking the same uncomfortable question — is the thing I built still serving the life I actually want, or am I serving it?
How you actually interrupt a pattern
Monika isn’t a rigid-framework person, so I pushed her on what interrupting these patterns concretely looks like, and her answer was refreshingly unmagical. Nobody books a coaching call to announce they’re a people-pleaser. They come because something feels off — they want to make a leap, or launch a new offer, or stop pulling all-nighters — and the thing they came in for is almost never the thing they end up working on.
She gave the example of a client fifteen years into business who was still pulling all-nighters she desperately didn’t want to pull. Underneath it: a belief that her worth came from delivering the best possible work in the shortest possible time, because if she gave herself a reasonable deadline, surely the client would pick someone else. So the fix wasn’t a time-management hack. It was a tiny experiment. Take the next two projects. Run one the old way for the cashflow. On the other, just try quoting the normal timeline and the real budget, and watch what actually happens. Disrupt the pattern once, on a small scale, and collect the evidence when the catastrophe you’re bracing for doesn’t arrive.
A lot of my methodology is to just try to disrupt the pattern.
It takes awareness first, then a willingness to do something with that awareness. The trying is the part that changes you, which is why Monika won’t promise anyone a quick fix — the things that are hardest for her are still hard for her, and she’s honest about that. This is a practice, the same way I tell people consistency is a practice. You’ll never arrive at some complete version of yourself; you just have to keep flexing the muscle and inching forward.
Undercharging is a pattern too
One pattern we both see constantly: the woman who does beautiful work, charges far too little, and can’t bring herself to ask for more — especially when her early clients are friends. Monika’s reframe came from her years in fundraising, where a mentor taught her that you’re not asking people for money, you’re offering them a chance to live in the world they want to live in. That framing carries straight into how she sees service work now.
I come at the same thing from the selling side, because so many of the women I work with simply do not want to sell. And what I always tell them is that refusing to sell is, when you follow it all the way through, a little bit selfish. You’re selling something that genuinely helps the person in front of you. When you undercharge or hide, you’re holding yourself back from helping as many people as you could, putting the whole business at risk in the process. This ultimately shortens how long you get to help anyone at all. Selling from a place of real connection, with a clear offer that meets a real need, is truly an act of generosity.
The work people skip
I asked Monika what most people rush past, and her answer was the inner work. We obsess over the pragmatic stuff — how to form the LLC, how to double sales, how to set up the systems — and all of that matters but you can mostly google it. What you can’t google is how to hold the belief that you can build this thing while life is happening to you. Monika built The Springboard through profound grief, having lost her brother, her father, and her mother-in-law across a few short years. The question that actually determines whether a business survives is whether you can keep showing up for something that doesn’t look bright and shiny yet, while everything else is hard.
That’s the part that, left unexamined, guarantees the same patterns just keep repeating in the next job, the next business, the next city you move to thinking the move will fix it. Those deep-seated patterns don’t care where you are because you take yourself with you everywhere you go.
One thing you can do this week
Monika gave a concrete starting move, and it’s small enough that there’s no reason not to try it. Pick a pattern you suspect you have — say, avoiding conflict — and just keep a tiny log for two weeks. This can be as simple as a line in your notes app each time you catch yourself doing it: what happened, and how it felt in your body afterward. For example: Someone asked me to do a thing I didn’t want to do and I said yes anyway, and it left a knot in my stomach.
You’re not trying to fix anything yet. You’re just building awareness. You’ll likely be shocked at how many times you engage in that pattern. On the conflict avoidance side, we picture conflict as one big dramatic moment, when really it’s a hundred tiny micro-surrenders a week. Seeing the actual count is usually the thing that makes someone realize they want support with it. You can’t change a pattern you haven’t caught yourself running into over and over and over.
I’ll leave you with this question: which pattern have you been blaming on your old job, when really it would’ve followed you anywhere? Catch it when it comes up this week. Only then can you decide what to do about it.
Work With Monika
Monika is offering five listeners a free North Star Session — 90 minutes of one-on-one coaching designed to cut through the surface-level noise and get clear on what you’re actually looking for. You’ll clarify your values, define what success looks like for you right now, and walk away with a real direction for what’s next. Just message her through this form and let her know you found her through this episode.
RESOURCES & LINKS MENTIONED
- Connect with Monika: Website | LinkedIn | Instagram
- Free North Star Session: Monika is offering five listeners a free 90-minute session — a space to figure out where you are, what your values are, why you started, and whether your business is still pointed where you actually want to go. Message her through this form to let her know you found her through this episode.
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