Lessons from corporate dropouts turned CEOs

Akua: When you first leave the comfort of a nine to five, you quickly learn that entrepreneurship isn’t just about freedom, it’s about growth, grit, and a whole lot of figuring out as you go. Every business owner has that one thing that they wish they’d done sooner or differently, and in today’s episode, we’re taking you behind the curtain of that hindsight and wisdom.

You’ll hear from three entrepreneurs who’ve each built, thriving, unconventional businesses on their own terms. They’ve been through the messy middle, learned from the hard lessons, and have come out stronger for it. If you have ever caught yourself wondering, what would I do differently if I started over?

Then this episode is for you. Well, let’s get into it. Welcome to Unbreakable Business, the podcast where we uncover the untold stories behind entrepreneurship. This isn’t about polished success stories. It’s about the sleepless nights, unexpected roadblocks and unshakeable grit that builds businesses that last.

Every week we sit down with entrepreneurs who face. All sharing raw, honest conversations about challenges, growth, and the moments that made them unbreakable. Whether you’re just starting out or chasing your next breakthrough, this podcast is your reminder that you have the strength to keep going. The landscape of work has changed drastically.

Layoffs before, once seen only as. Setbacks are now sparking unexpected opportunities. Professionals who once tied their identity and security to climbing the corporate ladder are discovering something more fulfilling and often more lucrative, which is independent business ownership. This episode shines a light on those voices, the corporate dropouts who stepped into entrepreneurship, not just for freedom, but for impact and possibility.

Instead of focusing on the struggle of leaving corporate life, we’re capturing the wisdom that comes after the clarity that only hindsight can bring. So we asked a simple question with powerful answers. If you were starting your business all over again on day one, what’s the one piece of advice you’d give yourself?

By weaving together these bite-sized answers, we’ll create a powerful narrative. Business ownership isn’t just an alternative to corporate life. It’s a future forward career path worth considering. First up is someone who knows the power of structure and growth. When you’re building a business, it’s. Easy to get caught in the creative chaos, but systems is what gives you freedom.

Here’s Audrey Kwan, founder of Agency Together, sharing the one thing she’d do differently if she were starting all over again.

Audrey: Hey, my name is Audrey Kwan and I am the founder of Agency Together, a community for agency owners, small but mighty agency owners to come together to connect, collaborate, and build referral ready relationships.

I also coach and consult with agency owners. I was on episode 76 of this podcast. And if I were looking back at my business and starting all over again today, the one thing that I would do differently or tell myself to do differently is to start thinking about capturing my systems and my processes. It is never too early to start.

Gathering how you do things into step-by-step ways, because at some point in time you’re gonna be really busy and it’s gonna get even harder to capture your systems and processes. So start in the beginning. They don’t have to be finalized. You can change them as they go, but when you have those in place, it is super easy to then hand it off to someone else to help support you in work so that you can then step.

Outta that work into other areas of your business and focus on really growing your business. I felt like I was a little bit behind in the beginning by not actually capturing the process and systems, and I got, I wanna say stuck, but not stuck. I just spent a lot longer time doing some of the work that I could have handed off so that I could step in, step into areas that allow me to grow my business.

Even more and, uh, help it to grow faster. I hope that idea sparked some thought for you and that it helps you grow your business smarter, not harder.

Akua: Next, we’re hearing from Jamie Gordon, a certified transformative and master life coach who brings heart and mindset into every conversation about success.

Jamie talks us through 11 powerful reminders that’ll help you build a business and a life that’s rooted in self-trust, curiosity, and courage.

Jamie: It’s Jamie Gordon. I’m a certified transformational and master life coach. I was a guest on the Unbreakable Business Podcast on mindset that makes you money. Here are 11 little things that if I was starting my business again, that I would really, really wish someone would’ve told me that I would incorporate into starting over from day one.

Here they are. Number one. Remember that failure is part of the journey. Number two, experiment. Don’t launch so you don’t have to be perfect. Experiments are meant to fail. Experiments are meant to collect data. Same thing with launching number three, who I am is not my business or my business success, or whether I’m profitable or not profitable.

That’s not me. That’s feedback about my strategy. Number four, stay curious and open-minded. Sometimes I go black and white and instead of being curious and I lose resource five, build pricing aligned with myself. Meaning if I need to upgrade my skills, get feedback, get referrals, know that wherever I start with my pricing is gonna be my referral base.

Just do the money mindset work ahead of time. Number six, address the fears or they will take you out. Look for the wisdom and the fear. Listen to those fears, but don’t let them drive the bus. Number seven, don’t wait to finish so you can feel the thing. Like if I’m gonna feel freedom, I’m gonna feel relaxed.

I’m gonna feel enough. I need to let myself feel it now, or I’m never gonna feel it when I get to the finish Line. Number eight, even out my negative fantasies, it’s no problem. The brain wants to give me negative fantasies, but I’m gonna discipline myself to, okay, I just spent 10 minutes spiraling about it going bad.

I’m gonna spend 10 minutes spiraling it, going good. Number nine, gamify where possible. You hate doing something, learning something new and it’s scary. I freaking go to Starbucks and do something fun with it. Gamify it. 11, keep your promises everywhere you are watching you. And if you are saying you’re gonna go to the gym and then you don’t go to the gym or you say you’re gonna do your laundry on Tuesday and you don’t do your laundry on Tuesday, these are like not.

Connected to your business, but they’re connected to your self-trust. And if you’re building your business, there is no greater asset that you can have than self-trust. Number 11, don’t kill the idea prematurely. Jamie. Don’t kill the idea prematurely. And maybe for you, you have an idea, you get excited about it, you hit one roadblock, and you’re like, see, it won’t work.

So don’t kill it prematurely. Kill it when it’s due time. You know, kick the horse, make sure it’s dead before you move on. Those are just some of the things that came to my mind that I hope will also help you.

Akua: And finally, Jenny Mack, the founder of Eloping, is Fun, has a reminder we all need, especially when business gets busy and success starts to snowball.

She’s taking us back to the heart of it all. Your why, because the reason you started might just be the

Jenny Mac: reason you’ll stay. Hi, I am Jenny Mack. I am the founder of Eloping Is Fun in New York City, where we help couples ditch the big wedding and do something fun instead. I was recently a guest on the Unbreakable Business Podcast with the wonderful Akua.

Uh, we spoke about the entrepreneurial superpower of listening to your clients to drive intentional growth. And if you haven’t listened to the episode already, highly recommend it. Um, so today, Aku, I asked. Me on to share some of my advice for people who are just getting into the game, starting their own business.

So if I had to do it all over again and I was starting my business today, the one piece of advice that I would follow, the thing that I realize has helped me so much grow my business over 15 years and have this like steady incline of just being successful every year, is to really focus on my why. You know, why are we doing what we’re doing?

Who are we serving? It’s something I. Review every year. It’s something that really helps inform the choices that we make of like how we grow, uh, how we’re serving our clients. And overall, it’s just the thing that gives me life satisfaction, you know, for running this business because. It’s, it can be a lot of work and it’s, it’s really hard.

But when you take the time to, to focus on that, not only does it give you a lot of focus and, and inspiration, and of course you know, we’re entrepreneurs ’cause we’re here to. Serve our clients and like make their lives better with whatever we’re doing. For us, it’s weddings. For us, it’s like trying to remove the whole stress part of weddings and just give people this really joyful, fun experience for their wedding day.

Simon Sinek is just an absolutely brilliant mind. Uh, he did the. TED talk. I think it’s like the most watched TED Talk of all time. Start with your why. So that gets into a little more of this concept. It’s also a great tool for, for your marketing when you really sit down and like I said, just think about who you’re serving.

So I would take. Take time, you know, every month, every year. And really look at that. Look at, look at your why. And I just wanna say, I wish you the best of luck. I think the more entrepreneurs in the world, the better. You know, we are the ones who are making a difference and serving people on a level that it, it’s just so personal and great.

So I think entrepreneurs are like the real backbone of society. Thanks guys.

Akua: Every entrepreneur’s story has a before and after, but it’s the lessons between those moments that shape us the most, whether it’s building systems, protecting your mindset, or reconnecting with your purpose. Remember this every so-called do over, it’s just another version of growth.

If you have loved today’s conversation, thank you so much for tapping in and share this with a fellow business owner who is also carving out their own path. And as always, until next time, thanks for tuning into Unbreakable Business. If you love today’s episode, don’t forget to subscribe, leave a review and share it with.

Someone who needs a little extra inspiration. Remember, no matter what life throws your way, you have the power to keep going and your business can be unbreakable too. Until next time, keep building, keep growing, and stay unbreakable.