I had a Medium tell me yesterday that I should lean into what feels natural in my career, and not fight against things that are ultimately coming my way.
I had just told her that I loved my coaching work and that I wanted to do it full-time. I then told her I had 25 clients, and she broke character for a moment and went wide-eyed.
“Twenty-five clients, that’s not a side hustle, that’s a business!”
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I laughed. Then she followed it up with the profound statement that has had me doing a lot of thinking.
Is this the time for me to go all in on coaching?
The truth is, I don’t want to work for a corporation anymore. I don’t want to answer to a boss. I don’t want to listen to someone tell me what to do, and I don’t want to be at the service of others unless I truly love the mission and I am bought in on what the vision is. Otherwise, I’d rather light my hair on fire, and trust me, I use a lot of hairspray, that shit will be torched in no time.
This particular Medium sort of opened my eyes for a moment. Is this the time? Should I just dive in? What’s holding me back? I guess it’s simple: health insurance and a cushy paycheck. But is that the reason to not do the thing I absolutely love? After all, I know how to make money, and I trust my abilities and my confidence to make it happen.
Next month will mark three years since I started this little journey. One particular client, the very handsome Ahmed Tawfik, has been with me for three years since he signed up as my first client. I’ll never forget getting the email saying I had a client. My first one. I thought someone had accidentally hit the wrong button. As I celebrate three years with my very first client, it’s got me thinking more and more about this little side hustle and what really needs to happen with it. It’s like Kylo Ren’s quote: “I know what I need to do, I don’t know if I have the strength to do it.”
Valaree, Brendon, and Cam will all hit three years by the end of 2026, assuming they don’t get sick of working with me. And multiple clients will hit two years this summer, including Cayla, Paige, and Bryan.
Something is going right.
The Medium is right. What feels natural is working with people to help them be their best in all facets of their career, and where that often intersects with their personal lives. Writing daily to help inspire and motivate careers, and creating products that add value, like my Career Stack on my website. Did I mention I launched Signal? A 24/7 AI-powered version of me that responds to all of your career questions and needs anytime of the day, in my voice? (I know you know already)
Speaking of my writing, it’s the people who come along on the journey with you that really make it. The first ten people to ever put down a credit card for my articles will be in my Hall of Fame for life. Aaron, my parents, Jesse, Lauren, Raffy, Cayle, Wade, Simon, Jim, and so many more. Oh, and they’re all still reading my content today.
Three years later, what feels right is answering the phone when I know someone needs help. What feels right is being there to answer a text at the end of a long day when someone has had a rough run-in with their client or leader. What feels right is just having natural conversations with people to normalize their crazy days and weeks. Everyone needs a support mechanism in their career. I don’t care how great you think you are; we all need a partner in the journey.
So I don’t know what the fuck this all means, but the Medium definitely isn’t wrong.
We all should lean in on what feels natural in our careers, and if you’re currently in a role, working a job, working a career, or doing anything that feels like work, feels against your values, your ethics, or just fucking drains, you then find something different.
The older I get, the more I realize that the feeling of being “stuck” usually has less to do with talent and more to do with honesty. Most people already know what they want to do. They already know what lights them up, what drains them, what gives them energy, and what makes them feel alive. The problem is that acting on those feelings usually comes with risk attached to it, and risk has a funny way of making us rationalize ourselves into staying in places that no longer fit who we are becoming. We convince ourselves that stability is fulfillment, when in reality, stability without purpose slowly turns into resentment if you sit in it long enough.
The funny thing is that when I look back over the last three years, none of this has actually felt forced.
None of it has felt manufactured.
I didn’t sit down one day and say, “I’m going to become a coach.” It sort of just happened naturally through an evolution of the dialogue I was already having with people, writing articles, helping with decisions, answering calls, building relationships, and showing up consistently for others during moments where they needed someone in their corner.
Somewhere along the way, this thing stopped being a hobby and started becoming part of my identity, and I think that’s the part the Medium saw immediately before I did. Sometimes other people can see your path more clearly than you can because you’re too close to it emotionally to recognize what is already happening.
What I do know is this: the moments in my career where I have felt the most fulfilled have never been tied to titles, compensation plans, or some giant corporate announcement about quarterly growth.
The moments that stay with me are the conversations after someone gets a promotion they didn’t think they could get. The texts from someone who finally found the courage to leave an environment that was destroying their confidence. The people who tell me they started believing in themselves again after years of feeling invisible. That’s the stuff I remember. That’s the stuff that actually means something to me. Nobody lies in bed twenty years later thinking about a really solid Q3 pipeline review meeting or their Google Doc they presented.
Maybe that’s the point of all of this. Maybe the goal isn’t to chase what looks impressive from the outside, but to lean harder into the things that feel the most natural to who you actually are.
The things that pull energy out of you instead of draining it. The things you would probably keep doing even if nobody was watching.
I don’t know exactly what comes next for me yet, but I do know this: when something continues to grow organically, continues to impact people positively, and continues to feel deeply aligned with who you are as a person, eventually you have to stop treating it like a side hustle and start respecting it for what it has become.
And for everyone who has been following along, you have absolutely no clue how much you mean to me. So thank you.