Stop Settling: The Question That Changed My Life!

We grow up believing that loyalty is always rewarded.

Stay at the same job.
Stay in the same city.
Stick with one path.

But what if the advice that's meant to keep you safe is actually keeping you stuck?

In this episode, I share one of the biggest mindset shifts I've had over the last few years: the difference between commitment and settling.

I talk about watching someone lose a 20-year career overnight, why I walked away from projects that no longer aligned with who I wanted to become, and why experimenting has taught me more than playing it safe ever could.

If you've been wondering whether it's time to make a change, this episode is for you.

In this episode, you'll learn:

• Why job security isn't what it used to be
 • The difference between commitment and settling
 • Why failure is information—not the opposite of success
 • How trying new things gives you clarity
 • The one question you should ask yourself regularly
 • Why your skills—not your job title—are your greatest security

This Week's Direction Challenge

✓ Run one experiment.
 ✓ Upgrade one skill.
 ✓ Ask yourself:

"Am I still growing here?"

If this episode helped you, subscribe and share it with someone who may need this reminder.

New episodes every week.

Transcript

SPEAKER_00 0:02

Hi everyone and welcome back to From Drift to Direction. I want to talk about one of the worst pieces of advice we've been given. Just stick with it. Stay at the same job, stay in the same city, keep doing what you've always done, focus on one thing, and look, I get it. Commitment is important. Consistency matters. But somewhere along the way, we decided that changing your mind was a character flow. You changed jobs, you moved again, you're starting another business. It's like people expect us to make a lifelong decision at 18 and then never update that software. And I think we've confused two very different things commitment and settling. Because here is what I've been noticing. A lot of people aren't stuck because they lack discipline. They're stuck because they've stopped growing and they've convinced themselves that staying is the same thing as being loyal. So that's what I want to talk about today. What happens when you stop settling? What happens when you give yourself permission to try things, to experiment, to upgrade your life until it actually reflects who you want to become. Let me tell you a story. I know someone. Let's call her Sylvia. Sylvia worked at the same company for over 20 years. 20 years. Same desk, same row, same routine. And she was fine with it because she had a plan. She was going to retire from there, she'd put in her time, she'd been loyal, she has done everything right, and in her mind, that loyalty was going to be rewarded. Then one Monday morning she got invited to a meeting with the HR. And let's be honest, nobody has ever walked into an unexpected HR meeting thinking, I bet they're giving me a yakl. She was let go. Restructuring, budget cuts, whatever corporate term they used that day, it didn't matter. 20 years of loyalty gone. And here's the thing. I'm not telling you this story to make you cynical about companies. I'm telling you this story because Sylvia spent 20 years waiting. Waiting for retirement, waiting for security, waiting for the company to take care of her. And in all that time, she never tried anything else. She never learned a new skill, never explored a side project, never asked herself, am I still growing here? She just stayed. Because she thought that's what you were supposed to do. And when the company made a business decision, because that's what companies do, they make business decisions. She was blindsided. Watching that happen scared me. Because I realized something. Your job security is your ability to adapt, learn, and stay valuable. And if you're not constantly growing, you're slowly becoming irrelevant. Your life is not in the company's hands, your life is in your hands. So here's what I learned from watching this happen. Your employer is responsible for running the business. You are responsible for running your career. Let me say that again. Your employer is responsible for running the business. And you're responsible for running your career. And I think a lot of us forget that. We think if we just stay loyal, if we just keep our heads down, if we just do good work, the company will take care of us. But that's not how it works anymore. Maybe it used to, I don't know. But it doesn't now. So instead of hoping your company invests in you, invest in yourself. Learn AI, learn sales, learn leadership, learn how to communicate better, earn certifications, build a network, read books, take courses, try things. Because here's the truth skills travel with you, job titles don't. Alright, so let me tell you about something I tried. About a year ago, I started organizing meetup groups. And I was excited about it. I thought this is going to be great. I'm going to build a community. I'm going to meet like-minded people. We're going to have these amazing conversations. And for a while it was good. But then I started noticing something. Every week it was the same thing. Who's coming? Who canceled? Did we hit the minimum? Is the restaurant still holding the reservation? Do we need to move to a different venue? And one day, I'm sitting at my desk looking at the calendar, and I realized I had accidentally become an event planner. Which is fine if that's what you want to do. But it wasn't what I wanted to do. So I started asking myself some questions. Why am I doing this? What am I actually getting out of this? Is this where I want to spend my time and energy? And the more I thought about it, the more I realized. I wanted to help people. I enjoyed the conversations. I enjoyed coaching people through their questions. I enjoyed creating content that made people think. But the logistics, the planning, the constant coordination, that wasn't it. And here is where it got hard. Because I knew I needed to stop. But I'll be honest, I wrestled with that decision for weeks. Part of me kept thinking, am I quitting too soon? What are people going to think? There are people who show up every week. Am I letting them down? I felt this weird sense of responsibility. Like I had started something, so I had to see it through. Even though seeing it through just meant more event planning, more logistics, more of the things I didn't actually want to be doing. And there was this voice in my head saying, just stick with it. You've already invested all this time, all this money for memberships. People are counting on you. But there was another voice, quieter at first, saying, You're spending all your energy organizing events instead of doing the work that actually lights you up. And I kept going back and forth. One week I would think, okay, I'll do one more month. Then the next week I'll be sitting there, confirming reservations, thinking, why am I still doing this? And it wasn't a clean decision. It was messy. It was uncomfortable. But eventually I realized something. The guilt I felt about stopping, that guilt was costing me more than the meetup was giving me. So I stopped. Not because I failed, not because it didn't work. But because I had learned enough to know where I actually wanted to invest my energy and my time. And you know what happened? The wor didn't end. People understood. Some people found other meetups. And I redirected all the time and energy into coaching, into this podcast, into creating things that feel aligned with what I actually want to build. The meetup wasn't a failure. It was an experiment that gave me clarity. And the guilt I felt about stopping, that was just me confusing loyalty with settling. This is not the first time I've done this. Let me tell you what I mean by that. When I first moved to London, I started a cleaning company. I know I ran them right, but at the time it made sense. I was young, I didn't really know what running a business looked like. And I thought, okay, people need their homes cleaned, I can do that. Scheduling, dealing with last-minute constellations. My mom was with me, we worked together for a few months. And honestly, it was hard. Not just the work itself. Though that was hard too, but the whole thing. Managing clients, trying to find a new client, printing flyers and knocking on doors, dealing with last-minute cancellations. After a few months I realized this isn't it. Not because I couldn't do it, but because it wasn't lighting me up. And here's the thing: if I had never tried it, I would have always wondered. But because I actually did it, I got clarity. I learned what running a business actually feels like. I learned that I don't want to build something just because it makes money. I want to build something that feels meaningful. That wasn't wasted time. That was information. Then there was the time I was writing articles for a well-known website. And I actually really enjoyed that. I loved the process of researching, writing, putting ideas together, and I learned a lot about storytelling, about structure, about how to communicate ideas clearly. But eventually I moved on. Not because it wasn't good, but because I realized I wanted to create something that was mine, not just to contribute to someone else's platform. And that clarity that only came from doing it. Then there was an e-commerce thing. I tried selling clothes online. Again, I didn't stick. But I learned about marketing, about customer service, about inventory management. Things I still use today in completely different contexts. So here's what I'm saying. Looking back, my resume doesn't look like a straight line. It looks like someone was playing connect the dots without the picture on the box. But every single one of those experiments taught me something about business, about myself, about what I actually want to spend my time doing. And if I had never tried any of them, I'd still be sitting around wondering what if. So when people ask me, don't you feel like you wasted time? No, I don't. Because the only way I figure out what I wanted was by trying things I thought I wanted. And realizing they were not. And I think that's the thing we get wrong about trying new things. We think if something doesn't work out, it means we failed. But really, it just means we learned something. So here's the insight I want to share with you. If you never fail, it means you never tried. And if you never tried, you never succeeded. We've been taught to see failure as the opposite of success. But it's not. Failure is just information. It's clarity, it's feedback. The opposite of success is not failure. The opposite of success is never trying in the first place. So let me ask you something. And if you don't have the answer out loud, just think about it. Am I still growing here? Wherever here is for you, your job, your city, your routine, your relationships, your habits. Am I still growing? Because I think that's the question we forget to ask ourselves. We get comfortable, we get into the rhythm, and we stop checking in. And then one day, we wake up and realize we've been drifting. Not because we didn't know what we wanted, but because we stopped moving toward it. So here's what I think. If the answer is yes, if you're still growing, then stay. Keep going, double down. But if the answer has been no for years, maybe it's time to evolve. And I'm not just talking about careers. I'm talking about everything. Maybe you've been living in the same city for 10 years and you've outgrown it. Maybe you've been saying you want to learn a language, but you never start. Maybe you've been thinking about starting a business, but you keep waiting for the right time. Maybe you've wanted to switch industries, but you're scared of starting over. And every time someone asks you about it, you say the same thing. Maybe someday. So let me ask you this. What are you actually waiting for? You know what the real cost of settling is? It's not just that you stay in the same place, it's that you start believing you can change. That's the part nobody talks about. When you stay somewhere for too long, not because you're growing, but because you're comfortable, you start to lose confidence in your own ability to adapt. And you tell yourself, I've been doing this for 10 years. I don't know how to do anything else. And the longer you stay, the more true that feels. But here's the thing, it's not actually true. You're just out of practice. The other cost, you become dependent on things staying the same. You build your entire life around the assumption that nothing will change, that your job will always be there, that your industry will always need you, that the world will exactly stay the same as it is. And then one day it doesn't. I've seen people get blindsided by this. People who spend decades in one place thinking loyalty would protect them, and then the company restructures or the industry shifts or technology changes everything. And suddenly they're starting over. Except now they haven't learned anything new in years, they haven't built new skills, they haven't expanded their network, they were standing still while everything else was moving. And here's where I realized if you're standing still while everything else is moving, you're actually moving backwards. Because the world doesn't wait for you to catch up. Now I'm not saying this to judge anyone, I get it. Settling feels safe. It feels comfortable. It feels like the responsible thing to do. But comfort in the moment often cost you later. And the thing is, most people don't realize they've been costing until it's too late, until they get laid off, until they burn out, until they wake up one day and think, wait, is this really it? And look, growth doesn't mean you have to be constantly busy or stressed. It doesn't mean you have to hustle 24-7 or never rest. Growth just means you're intentionally moving towards something you care about. You're learning, you're evolving, you're asking yourself what's next. And when you stop doing that, when you stop asking that question, that's when you start settling. So that's what I'm asking you. Because here's the thing life doesn't wait for you to feel ready. Life doesn't wait for you to have it all figured out. Life just happens. And if you're not intentionally choosing growth, life has a way of making the decision for you. A layoff, a burnout, a missed opportunity, a wake up call. So don't wait for life to force change. Choose growth before you have to. Now I want to be clear about something because I don't want you to hear this and think I'm telling you to quit everything after six months or start a new business every weekend or blow up your life every time you get bored. That's not what I'm saying. What I'm saying is regularly ask yourself that question. And if the answer is yes, stay. If the answer is no, but you're working towards something, stay. But if the answer has been no for years and nothing is changing, maybe it's time for you to try something different. Because life is not about finding one thing and staying there forever. It's about continuously becoming a better version of yourself. Better skills, better habits, better relationships, better opportunities. And if you're not intentionally growing, you're unintentionally settling. Growth begins the moment comfort stops making your decisions. You know what's funny? I've been thinking a lot about Sylvia lately. About what would have happened if she had asked herself that question, am I still growing here? Maybe she would have stayed at the company. But maybe she would have also started learning new skills, building a side project, exploring other options. And when that meeting with HR happened, maybe it wouldn't have been so devastating because she would have had other things going, other paths, other possibilities. Maybe she would have stayed, maybe she wouldn't, we'll never know. But I do know this. The people who thrive aren't the ones who never change. They're the ones who keep evolving. They're the ones who try things, who experiment, who are not afraid to look back and say, you know what? That didn't work. Let me try something else. And I think that's the real difference. It's not about having it all figured out. It's about being willing to figure it out as you go. So don't settle because it's comfortable. Experiment because growth requires movement. But here's what I hear a lot. People say, yeah. That sounds great, but what if people think I'm crazy? What if I try something and everyone judges me? What if I fail and look stupid? What if I waste my time? And I get it. Those fears are real. But let me tell you something. People are not judging you as much as you think they are. You know why? Because they're too busy worrying about what you think of them. Everyone is so caught up in their own lives, their own insecurities, their own problems. They don't have time to sit around analyzing your career moves. And the people who do judge you, they're usually the ones who are not doing anything themselves. So if someone is giving you a hard time for trying something new, ask yourself, is this person living the life I want? If the answer is no, why are you listening to them? Okay, but what about failure? What if I try something and I'm terrible at it? Then you learn you're terrible at it and move on. And that's actually valuable information. Because now you know. You're not sitting around wondering, maybe I would have been great at that. You tried it, you were not, you moved on. And you can move forward with clarity. And here's the thing about wasting time. People say, but what if I spend six months on something and it doesn't work? Okay, but what if you spend six months doing nothing? And you're in the exact same place you are now? At least if you try something, you learn. You build skills, you meet people, you figure out what you don't want. Time spent learning is never wasted. And look, I know there is this fear of commitment too. What if I start something and then don't finish it? So what? You don't have to commit to something forever just because you tried it once. You are allowed to start a business and shut it down. You are allowed to take a class and realize it's not for you. You are allowed to move to a new city and move back. Trying something doesn't mean you're signing a lifelong contract. It just means you're curious. And yes, sometimes you're going to look silly. And I remember when I first started this podcast, I had no idea what I was doing. I didn't know how to edit the audio, I didn't know how to structure an episode. I'm pretty sure my first few recordings sounded like I was talking into a tin can. But you know what? I did it anyway. Because looking silly is the price of growth. Every single person who has ever done anything interesting has looked ridiculous at some point. They've stumbled, they've made mistakes, they've tried things that didn't work. But they did it anyway. And here's what I've learned. The people who have the best lives are not the ones who never tried. They're the ones who are willing to look stupid. And if you're sitting there right now thinking, but I don't know what to try, try something that moves you toward the person you want to become. Seriously, just pick something and try it. Because you're not going to figure out what you want by thinking about it. You're going to figure it out by doing it. And yes, some things will not work. Some things will be a waste of time. Some things will teach you exactly what you don't want. But that's still information. That's still progress. And that's still better than sitting in the same place wondering what if. Okay, before we wrap up, I want to leave you with three things to think about this week. Three simple actions that can help you stop settling and start growing. This week's direction challenge. One. This week, run one experiment. Apply for the job. Sign up for the class. Start the side project. Reach out to someone you've wanted to connect with. It doesn't have to change your life. It just has to teach you something. Because here's the thing: the goal is not success. The goal is information. Number two, upgrade one skill. Pick one skill that will still belong to you five years from now. Maybe it's AI. Maybe it's communication. Maybe it's public speaking. Maybe it's sales. Maybe it's learning another language. Companies can take away your title. They can restructure, they can lay you off, but nobody can take away your skills. That's what I learned from watching Sylvia's story. Your security is not in a job. It's what you know. And finally, number three, ask yourself one question. This Sunday, sit somewhere quiet. Leave your phone inside and ask yourself. Am I still growing here? Not whether you're comfortable, not whether it's familiar, not whether it's easy. Am I growing? That's the question. That's the one that matters. See you in the next episode of From Drift to Direction. Thank you.