As summer winds down and fall creeps in, I’ve been reflecting on what it means to be self employed. Both literally and emotionally. What I’ve learned, what I’m still learning, and how the lessons keep showing up even 12 years later.

I’ve been procrastinating on writing this blog hence why you’re reading it now, but last night, while cleaning out my closet, I found an old ID that stopped me in my tracks.

There she was: 2013 Karen. Side part. My favorite royal blue shirt. Smiling so big because I thought I’d made it. I was working at the Boston Symphony, surrounded by the greats, immersed in history, and soaking up what I believed was the pinnacle of excellence. I was convinced I was going to make it big there. Or so she thought.

Fast forward to fall of that year: bright eyed me had just been promoted to full-time employment. I’d gone from selling tickets at the box office to selling subscriptions to our wonderful (and mostly patient) patrons. I was proud, my family was proud. I was the top seller on my team, I was organized, I was driven. The only catch? I was the only person on my team whose family lived out of state.

So when the holidays rolled around, I asked if I could take off two holidays instead of one. It didn’t seem like a big ask to me. I'd earned it, and I was delivering in my role.

But one morning, my boss, a middle aged white man who, let’s just say, wasn’t exactly keeping up with the rapidly changing ticketing technology, denied my request. Not just denied it, but threatened to fire me if I didn’t show up.

I was 23 years old, floored. My American dream of building a legacy within the symphony world evaporated in that instant. And in its place was a familiar, gut punch feeling: the reminder every immigrant carries that your security is always conditional. That no matter how hard you work or how well you perform, someone else’s mood or decision can strip it away in a second.

As a recent grad, to experience that reality twice in a year felt cruel. (Story for another day of course) But also clarifying. Because that afternoon September 11, 2013, on my lunch break I walked into Bank of America on Mass Ave and, in very Enneagram 8 fashion, opened my first business account.

And that was the day everything changed.

That moment was the beginning of my self employment journey. I didn’t have a business plan, fancy branding, or even a clear idea of what my business was going to be. What I did have was conviction and maybe a little stubbornness that no one was ever going to have that kind of power over me again. I was determined to prove that I could still work with the greats even if my title or the association was not a fancy organization but my own name.

Twelve years later, I’m still here. I'm still learning. Still messing up. Still celebrating. And honestly? Still figuring it out.

Here are a few lessons I’ve learned (and am continuing to learn) about being self employed:

1. Freedom comes with its own weight.

Yes, I get to make my own choices, design my schedule, and create work that actually lights me up. But that freedom comes with the weight of responsibility. No one is handing me a paycheck just for showing up. If I don’t advocate for myself, no one else will. The ebb and flow of freedom was a double edge sword when my journey of motherhood began. How do I pay myself? Will my clients leave? There is no paid leave in the United States for self employed folks, will my baby ruin my career? I wish I could go back and hug that version of myself. The worrying about it did in fact not help, BUT the mindset of “ we don’t rise to the occasion we sink to the level of our systems” did. Enter the operations genius that is my business partner Jen.

2. Security is something you build, not something you’re given.

That old job showed me that so called “job security” isn’t always real. But building my own safety nets whether through financial planning, multiple revenue streams, or community engagement has given me a deeper sense of security than any W2 ever did. Also security comes from financial literacy and learning that some day my organization could give me a W2 and even crazier to think, it could also give someone else a W2 is wild. This year we celebrate two full time W2 employees.

3. You don’t have to do it alone.

Early on, I thought being self employed meant being a lone wolf. Over time, I’ve learned that collaboration, mentorship, and support systems are not weaknesses; they're the things that keep you from burning out. Yes protect your intellectual property and ideas but be open to collaboration, you never know what relationship steers the ship of inspiration.

4. Growth is not linear.

Some years feel abundant, others feel like a slog. And that’s normal. It doesn’t mean you’re failing. It means you’re human, and that your business is alive and evolving with you. Let me say it again “ Growth is not linear” my God. The amount of voice memos I send my colleagues and even my business partner Jen moping about how I should just have it all figured out by now. "What do you mean the numbers have gone down, what did I do?” The warm embrace of community always reminds me that it’s nothing I did but simply the ebb and flow of the business, and how growth looks different in different seasons, how annoying, right?

5. It’s okay to start over.

That ID card reminded me that 2013 Karen thought she had it all figured out. And here I am, a decade plus later, still starting over in new ways, new goals, new services, even new ways of relating to work. Self-employment isn’t about “arriving”; it’s about staying open to reinvention. I’ll leave you with this quote that we always cite incorrectly; “ A Jack of all trades is a master of none, but oftentimes better than a master of one.” Do the thing fearlessly.

So if you’re in a season where you’re questioning your path, or if you feel the ground shaking under you, maybe that’s not failure. Maybe that’s your invitation to step into something new.

Because if there’s one thing I know for sure, it’s this: sometimes the “no” that floors you is the very thing that opens the door to the life you were meant to build.

Download our 12 Q's for Music Entrepreneur Freebie

I’d love to hear from you:

Have you ever had a moment where you realized the “security” you thought you had wasn’t real?
Or maybe a time when a setback ended up being the push you needed to build something better?

Drop a comment or send me a message. I always love hearing these stories. We learn so much from one another when we share the messy parts, not just the highlight reel.

And if you’re in that “what now?” stage of your career or business, let this be your gentle reminder: you don’t have to have it all figured out to take your next step.

Done > Perfection