What Most People Get Wrong About Success

Update: 2025-10-16

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Episode 994: Show Notes

Have you ever hit a milestone you worked your entire life for only to feel absolutely nothing? We often spend so much of our time and attention focused on our future selves that we forget how to live in the present. But it’s not your fault! We were handed this invisible checklist when we were all kids. We’re supposed to get a good education and a good job, buy that house, get married, have those kids, and live that dream life.

We all thought we would feel a certain way if we did what society said would make us successful. But none of these things actually change who we are. It doesn’t change the emotions we experience in the moment. It just makes us compare ourselves to this inconceivable, impossible representation of what success looks like.

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We’ve created a culture in which we are rewarding the outcome, not the effort. You have to beat yourself at your own game and outdo yourself every time. But eventually, outdoing yourself becomes impossible. Even if you’re not playing the comparison game and you’re only focused on you, how can you continuously do better than yourself all the time?

The One Thing I’m Learning About Success and Life Right Now

My career has been pretty incredible. I’ve been featured in Forbes and INC, this podcast has been called one of the best for entrepreneurs, I’ve been interviewed by some of the most brilliant minds in business and by CNBC, filmed for a television show, and recorded nearly 1,000 podcast episodes. I’ve worked with over 40,000 small businesses. My website has been read in 189 countries. And that’s just the beginning.

But today, just sitting feels like an accomplishment. I’m on Day 10 of IVF stimulation medication. I’m so excited about starting my own family, and also incredibly overwhelmed by what that looks like. So many of us find ourselves here — where the good and the hard are tangled together. The things that once empowered us can turn into rules we feel we must follow, or else we’re failing. If we don’t undo these patterns, I think we risk staying stuck — without a path forward

What I Learned When I Finally Slowed Down

This year, I’ve been on my own sort of Eat Pray Love journey. Not necessarily spending a year abroad gallivanting across Italy and India and Bali, but I’ve been trying to rediscover what I really want. I’m moving my body more, and that feels great. I’ve spent more time in prayer and reflection and community. All of those things have helped me to be more present and to feel more content. This morning, after my walk, I was having breakfast in the sun and I realized that everything I ‘had’ to do today was optional. The reason I was able to get there is because of three misconceptions I’ve blown up this year, and today I want to share them with you.

The first one? Success is about doing more, that we need to grow constantly, scale, expand, and better ourselves. We look for validation and applause. But more is often a disguise for not actually knowing who you are. Who are you without the business? Is your whole identity based on being a founder? Have you been in survival mode for so long that you don’t know what peace feels like anymore? I’m terrified for what’s next unless you let that go.

How We Lose Ourselves Trying to Follow Someone Else’s Path

We know there’s no one-size-fits-all approach to business, yet we’re always looking for one. My right time and your right time could be dramatically different things, but that doesn’t make it any less or more successful. You could, of course take someone else’s steps and go far. I’m not saying that learning from other people is a bad approach. I’ve spent the last ten years teaching online, so I see the value in it.

But the issue comes when we feel like we have to do it exactly like someone else, and when we force those square pegs into a round hole, and it doesn’t fit, and we feel uncomfortable the whole time, it’s not going to feel good. And it’s not to say that you should always be comfortable. Success isn’t about always having the best day ever or feeling like you have enough, but we can’t continue to think that if we all have the same set of things, we will all feel good.

Why Success Isn’t Going to Make You Feel Safe

Even if you have the things that make you feel successful, that illusion of stability, having more money, more status, more control — it’s not going to be what quiets your nervous system. If you’ve been stuck in survival mode for so long, living in anxiety and burnout and disconnection, suddenly having money land on your lap is not going to make those things go away. You have to heal on your own.

Money obviously gives you space and choices, and I am not denying that, but it’s not going to make you feel safe all on its own. You’re the one who has to work through your insecurities and the things that have left you broken along the way. If anything, trying to control the amount of money you make, the status you have, and the safety nets all around you, is only going to make you more anxious. If you’ve outgrown the metrics you measure your success on, achieving more is not going to create a new experience.

What It Might Look Like to Put Yourself Out There In New Ways

Things have to shift. We have to tell ourselves need stories. We have to get super curious, and this isn’t about pulling ourselves away and doing a whole bunch of reflection. If anything? I’ve put myself out there more and in new ways. I wonder if success isn’t something you need to chase at all, but something you need to define for yourself. What if it had less to do with what you’re building and more to do with how it feels?

What if you could love your life right now even if it’s not exactly what you expected? I’m not saying you need to know what success means to you or how it’s going to look or how you’re going to get there. In fact, I want you to be thinking about what you should be building that you actually want to maintain. What do you want your day to day life to look like? How can you have more of that now? If you stopped trying to prove your worth by achieving more, what would you do instead?

I think most people get their idea of success wrong because it was given to them by someone else. I’m so excited to be writing the book that’s going to help you rewrite that future.