Feeling Professionally Stuck? Here’s What Worked (& Didn’t) For Me

A year ago I felt professionally stuck and it was eating away at me, so I made a birthday wish to “love what I do for a living” by my next birthday and thanks to the revelations I’m about to share with you — my wish came true!

(I’m co-founder of Raddle — the virtual brainstorm community of solopreneurs who bounce business ideas around with unlike minded strangers.)

Before I get to those revelations, I’m going to share a bit about what led to them. For those who feel professionally stuck right now, I think it might help.

But this won’t be another ‘how I made it’ startup story (which you should avoid at all costs.) It’s more of a ‘how I made it out of the gate’ story. (I have no idea how my story will end, which is scary as fuck — but good scary.)

My Lead Up to Feeling Stuck

Lots of people are totally cool working a job they deem ‘good enough’. It may not be their calling, but it meets their needs. Good for them!

But that’s not me. Is it you?

I’ve had a nagging dream to be an entrepreneur my entire adult life (and much of my childhood too). I didn’t know exactly what that looked like, but I had a growing suspicion that it should involve helping everyday entrepreneurs succeed.

I got a taste while working with fair trade entrepreneurs around the world. I saw how profits generated from hard work transformed lives, families, and communities. In Africa, Asia, North, South and Central America —I spotted the same unmistakable expression of pride on entrepreneur’s faces who were earning their way to a better life by creating something passion-driven.

That’s a basketmaker and me in KwaZulu-Natal, South Africa

I enjoyed that work and subsequent jobs but yearned to make a living as an entrepreneur myself. But I couldn’t seem to make it happen.

This caused me a lot of pain and shame. It also led me to question my abilities even though I knew deep (like — really deeeeep) down inside that I have what it takes.

I was an entrepreneur in my heart, but I didn’t have a business of my own. So what did that make me?

According to my brain — a failure. I felt like a musician with no instrument.

It didn’t help when a well meaning friend advised me to launch my own thing first, be successful at it, and THEN help other people do the same. Because every time I tried, it did not end well.

One time in particular, I cleared my schedule and set aside two whole days to figure out how to launch my own something. The goal was to decide on one thing (I had SO many ideas), create a plan, and start executing. I’d tried many times before, but not with two whole days dedicated to nothing else. I told myself, “This is it! THIS is the time everything changes.”

I was all…

Unfortunately, my brain had other plans:

“Here we go again.” “Been there, tried that.” “I’m too late and too old.” “Someone’s already doing this.” “It’s not worth it.” “I’m wasting so much time.” “I can’t handle being an entrepreneur.” “Just give up and get a job.”

And the finale: 👇

So what WAS wrong with me?

Abso-fucking-lutely nothing, unless you call being human wrong.

Yes — I was having trouble moving forward, but not because I lacked talent or ability or because I sucked at being human. And no — the irony that I was failing at doing what I hoped to help others do was not lost on me.

I just needed a new approach, because what I’d tried wasn’t working. And this new approach needed to account for my brain, which was actively working against me.

I needed to figure this out — not just for myself, but to help other people who were struggling to figure out their next professional step.

I cried to a close friend, “How can I help others get unstuck when I can’t even get myself unstuck?” Her response was perfect: “Maybe helping other people get unstuck is how you’ll get yourself unstuck.”

It turns out she was right.

I turned 50 years old last week. As I blew my candles out, I realized that I needed a new wish because I love what I do for a living. How cool is that?!

Did I wish that I knew what I know now when I was younger? No, not literally. (Even if I had — I can’t tell you my birthday wish!)

I mean — of course figuring this stuff out earlier would’ve been great, but there’s no use beating myself up because it took me till 50 to find my calling.

Not dwelling on regret, I‘d much rather spend my energy sharing what I’ve learned to spare you and others the same pitfalls. So here goes …

Realizations, startup tips, and mind hacks I wish I discovered sooner because it would’ve saved me a lot of grief:

1. You’re ready enough. Instead of learning or planning or preparing more —start throwing things at the wall and see what sticks. The best way to figure things out is to start doing, not studying how or preparing to do them. No joke: planning for me lasted years and in retrospect — was just a sneaky way of saying “never.”
2. You can choose your specific business idea later: I assumed (incorrectly) that at the very least, I needed to know what exactly I aimed to build or create in order to start. It turns out — that’s not necessarily true. I’d describe it more like this: you need to have a ballpark idea of what you aim to achieve, not exactly what or how. Take Raddle, for example. We (my co-founder and I) knew we wanted to help solopreneurs build WITH others, but what that looks like evolved over time. (Heck — it’s still evolving!)
3. You do not need to know your destination to leave the station. Pretend your business is a 6 month Eurail pass. You don’t know exactly where you’re going to end up, or when. You just know that you’re most likely going to have one helluva a great adventure. Yeah — look at your business like that.
4. Get out of your head and into action. Beating back the negative voices in your head is a battle you will never win. It’s o.k. to lay your sword down and walk off the battlefield. Let it rage on without you. You owe it nothing. When negative thoughts emerge (and they will) — acknowledge them, then gently let them pass.
5. Nike was really onto something. Are you the type of person who likes having a plan and knowing all the answers before you start? Well GET OVER IT! When it comes to most things business-related, the best way to learn is by doing, not planning to do or studying how to do. So JDI!
6. Go ahead and fuck up. Are you the type of person who does not like to fuck anything up ever, especially in public where people whose opinion matters to you can see you fucking up? Well GET OVER THAT TOO! It’s imperative that you embrace failure. Aim to fail fast and often. It’s how you’ll end up with the best result. Trust me when I say — it gets easier the more you do it. And saying “Sorry” or “Oops” will always have your back.
7. Our brains are programmed to keep us safe in our comfort zone. ‘They’ say that outside of your comfort zone is where the magic happens. Yup! But that’s not what your brain wants you to do. When our cavemen and cavewomen ancestors were rocking it, they knew that leaving their cave alone, away from fire/food/shelter meant certain death. Human brains are programmed to keep us alive which means — do not step out of the cave lest you perish. If you’re going to get unstuck — you need to ignore what your brain is prompting you to do and leave your cave.
8. (The good news about ^) Being uncomfortable gets easier the more you do it. What’s really cool is that the more you hang outside of your comfort zone — the more comfortable it feels. Crazy, right? I know!
9. We are social creatures, so solopreneurs plz don’t build alone. If you want to own your own business, don’t grow it alone. That’s pretty much the worst idea ever. Find some way to build WITH others. I’m not talking about getting advice along the way. I’m talking about building WITH other people to help keep your momentum going. Find a mastermind group or join a community to build with (like Raddle 😆) or start your own! (People & Co can show you how.) Or do what I did — find a ying to your yang business partner. (That’s been a game changer for me.) By building WITH other people I’ve figured out a way to evade my biggest adversary — my mind.
10. Quit reading those damn ‘How I Made It’ stories. They’re soul crushing. ‘Learn from my mistakes’ my ass. Most of them just leave you feeling inferior with some serious catching up to do. We all know how the story ends. They make it! Where’s the vulnerability in that? If you really want your story to help others — share it with other people BEFORE you know your ending. That’s some rock star shit right there. Those are the people all of us grinders need to hear from and build with.
11. Accept that you’re here now. If I continued to beat myself up about how far from my professional goals I was given my age I probably would’ve remained stuck. Accepting that ‘I’m here now’ enabled me to move forward. (This realization didn’t come from me, it came from a lesson gleaned from the book “Designing Your Life”. I recommend it to anyone who feels professionally stuck. They’ve got a new book Designing Your Work Life which I haven’t read yet but reviews have been great.) One thing to add about accepting that you’re here now: it should include making peace with your age.
12. Be patient with yourself. I probably would’ve told you to fuck right off if you told me this a year ago. Because at my age — I felt like I had wasted so much time that I had catching up to do. But that was just a story I made up in my head. Whether I took it as truth was entirely up to me. I chose not to. I believe that I’m right where I need to be. Patience is important when you’re trying to get unstuck because you need to try lots of things. If you’re constantly worried that you’re out of time—you’ll waste precious energy worrying instead of trusting your process.
13. You can be yourself, faults and all, and still command respect. “Establish yourself as an expert.” “Become an influencer.” “Position yourself as a leader in your field.” That’s all well and good, but you can do all of that while remaining true to who you are. Now more than ever — people are craving authenticity, so be yourself. Providing real value to your customers is what matters, and what people will pay for.
14. Don’t set out to launch your own anything. My whole “today I’m going to launch a business!” approach was destined to fail. I should’ve set out to do one small step, and then another, and another. At that point, momentum kicks in (yay science!) and before you know it, your starting gate is just a distant memory.
15. Shame on you? (This one may read a little mushy but bear with me because it’s CLUTCH!) Check in with yourself to see if you have unresolved shame issues. (I did.) If you do too—and LOTS of people do, they’ll rear their ugly head into virtually everything you think and do until you either deal with them or remain stuck. Rather than fumble through elaborating, watch the shame tamer herself — Brené Brown:

Like I said at the beginning — I have no idea how my story will end, but the relief and joy of getting to do what I love is its own reward.

Regardless of what happens with Raddle — I’ve already won. When I wake up each morning, I’m excited to help solopreneurs get out of THEIR head and keep building forward. Our beta is invite-only but you’re welcomed to request an invite.

If you take one thing away from all of this, it’s that to find your voice, you have to use it.

I hope that my journey inspires you to keep pursuing your dream no matter how stuck you feel, whether it’s launching a business or pivoting in your career. Clearly, getting unstuck isn’t easy or fast but it’s possible, whether you’re 50 years old or 80 or 20.

Want to do me a solid? This is my first Medium article, and no lie — it took me months to muster the courage to put it out there. But I’m here now 😀 If it helped you, I’d greatly appreciate your shares and clap.🙌