The Sheila Botelho Show: Business Strategy and the Inner Work of Leadership

Why Do I Suddenly Feel Like I Can't Do the Thing I've Already Proven I Can Do | EP 619

Sheila Botelho | Business Strategist

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0:00 | 14:52

Years ago I ran two corporate events, fifty people each cycle, without a shred of doubt. A handful of years later, trying to do something similar in my own business, the exact same task felt daunting.

This episode is about what actually changed, and why the fear you feel around something you've already proven you can do usually isn't telling you what you think it's telling you.

Full show notes, transcript, and chapters at sheilabotelho.com/619

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A Memory Of Easy Confidence

Sheila

There's a memory I go back to often from years before this business existed that still teaches me something every time I think about it. In this episode, I am taking you back to two events I ran a long time ago, 50 people each over two days, and to the very different feeling that showed up years later when I tried to do something similar on my own. I've built through two entirely different chapters now, one with a team and a budget behind me, and one without. And I know the difference in my body. I'm walking through exactly what that difference taught me about where confidence actually comes from. So stay with me because if you've felt this way before, perhaps you've called it something else. Hi, welcome to the podcast. I'm Sheila Botelho, and I believe true success is built from the inside out. I want to take you back a number of years to a version of me who could plan and deliver a two-day event for 50 people without breaking a sweat over it. And I want to sit with that memory for a little while today because I think it's teaching me something that I'm still learning from, even now. Now, this was years before this business existed, back when I was doing corporate event organization, the kind of work we're selling and delivering an event of that size was actually just part of the job. And I ran two of these events, each one over two full days, and each one holding 50 people in arounds in the room. And I remember the feeling of it so clearly because it was such a specific kind of confidence. I wasn't nervous. I wasn't circling the same three worries at two in the morning. And I moved through the planning of those events the way you move through something that you've already proven that you can do, checking off logistics, making calls, solving problems as they came up, and all of it with a kind of ease that I only fully appreciate now. And looking back at it from where I'm standing today is a little different. So I wanted to slow down on this because I think this is the actual heart of what I'm talking about

Skill Plus Scaffolding

Sheila

today. And that is that confidence was not only coming from my own skill, it was coming from everything around my skill. I had a team. If something needed to happen that wasn't my strength, someone else on that team had it covered. And I could delegate it without a second thought. I had a corporate account behind every decision, which meant the financial risk of the whole thing was never sitting on my personal shoulders alone. If a vendor needed to be paid, if the room needed to be bigger than we'd planned, if something had to be fixed at the last minute, there was an entire structure absorbing that weight. I could go talk to my CFO. It was fabulous. I was skilled and I was also held. Both of those things were true at once. And at the time, I don't think I could have told you how much of my confidence was actually the second one.

When The Same Work Feels Daunting

Sheila

Now, let me take you forward a handful of years into a very different season of my life. I had my own business by then. And I wanted to do something similar: a gathering, people in a room from my team in the business I had grown with my husband. The kind of experience I knew how to build because I'd built it before, more than once, very successfully. And what I felt sitting with that idea was not the same steady confidence from years earlier. Truly, it was daunting. All of a sudden, something that I'd already proven I could do felt like it was sitting just out of reach. And honestly, it was so strange to sit with that because I had to literally talk to myself because I hadn't lost the skill. I knew how to plan an event like that. I'd done it so many times. And for large groups of people. So why did the exact same task on paper feel so different in my body the second time around? And here's what I eventually understood. And I think it's one of the more useful things that I can hand you today for where you may find yourself. The daunting feeling wasn't about capability at all, it was about infrastructure. In the corporate version of that story, I had a team to delegate to. And in this new version, it was just me. In the corporate version, there was an account absorbing the financial risk. And in this new version, every dollar and every decision was mine to carry. The skill obviously hadn't gone anywhere, but what had disappeared was the scaffolding that used to hold a piece of that confidence for me in the background the whole time.

Fear Often Signals Lost Infrastructure

Sheila

And that's why I'm talking about it. Because many of us are carrying skills forward from an earlier chapter. And it can be so easy to forget that. Maybe it was a corporate career, maybe it was a role inside someone else's company, someone else's team, someone else's budget. And when you step out on your own and you try to do the thing you already know how to do, the fear that can show up can be misread almost every time. People assume it means they've lost their nerve or that they're not actually as capable as they thought they were. And truly, I don't think that's fully what's happening. It may be that the scaffolding changed and the skill is being asked to stand entirely on its own for the first time. So I want to talk a little longer about this because this applies far beyond event planning. It's just an example I pulled out of the air. And I want you to hear how wide this actually can reach. This shows up when a corporate leader who ran a department of 20 people steps into consulting for herself and suddenly can't imagine handling client work alone, even though she managed far more complexity than that inside of her old role. It also can show up when a founder who built one business inside a supportive partnership goes to build a second one solo and finds themselves doubting decisions they used to make in seconds. It shows up for the brick and mortar owner who once ran a location backed by a franchise system, and every process already was built up. And now they're opening something entirely on their own with none of that structure standing behind them. It shows up for the licensed professional who spent years inside a firm's infrastructure, malpractice coverage, an admin team, a referral pipeline already built, now hanging their own shingle and feeling the ground shift under decisions that really they've made a thousand times before. Truly, it shows up anytime that the invisible skill stays exactly the same while the invisible support underneath it changes shape without anyone noticing. And because the support was invisible in the first place, we just don't think about it. Most people never consider it when their confidence disappears. They look at the skill instead and they start to doubt the wrong thing entirely.

Build For Your Current Reality

Sheila

So once I understood that about myself, everything shifted in how I approached building something new. I stopped trying to recreate the corporate version of that confidence, the team, the account, the built-in safety net. Because chasing that felt like waiting for permission that was never going to arrive the same way twice. And instead, I started asking a different question entirely. What does this actually need to be given what I actually have right now? Not what I used to have, not what would make this feel exactly as safe as it did back then. What does this specific version built by me on my own resources actually need to be to get started? And that question changes everything about how you build. It means the event, the offer, the gathering, whatever it is you're building, gets designed around your current reality instead of a borrowed one. And it gets simpler in the places that need to be simpler. It gets more honest about what you can hold on your own. And it stops depending on infrastructure that isn't there anymore to prop up your sense of being capable. And something I find so interesting is that the confidence that comes back after that shift is actually even sturdier than the one that I had years ago because this version belongs entirely to me. Nobody delegated a piece of it to me. Nobody's account was softening the risk behind the scenes. It was mine, all mine, built from the ground up. And that means it doesn't disappear the next time the scaffolding changes again because there isn't any scaffolding left to

Ownership Matters More Than Scale

Sheila

lose. There's something else worth naming here, too, about the several events that I ran back then compared to what I'm doing now. Those corporate events were excellent. And they were also, in a sense, not fully mine. I executed brilliantly inside a structure someone else had built and funded. And what I'm building now and have been building is even though on a bit of a smaller scale than they were doing, it starts entirely, start to finish in my mind. And it moves forward in a way that those events were never designed to move forward. I used to think that bigger automatically meant better, more resourced, more impressive. And now I don't think that anymore. Big is great, don't get me wrong. I just think that ownership matters more than scale to me right now. And I'd rather build something smaller that's completely mine than something larger that's still borrowing its foundation from somewhere else. There's this kind of pride that comes with the corporate version of success. And it's well-earned and definitely worth holding on to. There's a different kind of pride that comes with the version that's entirely yours, built without anyone else's safety net underneath it. And I think founders and visionaries can really understand this. I've come to trust that second kind more because it doesn't depend on anyone continuing to hold up their end of a structure that I never controlled in the first place. So if you're standing in a moment like this right now, looking at something that you've technically already proven you can do, feeling a version of fear you can't quite explain, given your own track record, I invite you to ask the same question I had to ask myself. Is this actually about capability? Or is it about the structure that used to be standing behind me? Those are two completely different problems. And only one of them requires you to doubt yourself. The skill was always there, and it still is. What's being asked of you right now is to build a new kind of confidence, one that isn't borrowed from a team or an account or anyone else's structure, one that belongs to you because you built it with your own hands from your own mind, in whatever form your current resources actually allow. And that version takes longer to arrive at, but it can also hold really strongly.

Rebuilding Confidence With The Right Support

Sheila

And I'll say one more thing about this because this is the part that matters most for perhaps where you may be standing right now. Building this new kind of confidence is not a solo project either. Even though I'm saying it's yours, this is your business. You know, it belongs entirely to you once it's built. Truly, I found that through the same principle I talk about in every episode, these are the things that are important. Being witnessed, being reflected, being guided back to what I already knew instead of trying to white knuckle my way through it alone. So the scaffolding I lost wasn't a team that I could delegate logistics to. It actually became a different kind of support that I could create for myself. People who could reflect back to me while I rebuilt something that was mine from the ground up. And that is available to you too, whatever season you're standing in right now. I think about those two corporate events often. And I'm proud of them. I'm grateful for them. They taught me how to hold a room, how to manage complexity, how to deliver something at scale under pressure. And none of that knowledge has left me. What I've had to learn since is a separate skill entirely among many. And when those events never actually asked of me, because the structure around me was doing that particular job the whole time. And that is learning to build without that structure. It made whatever I build now genuinely mine in a way that nothing before it ever was. And I wouldn't trade that. Even on the days it feels like the harder path.

The Question To Ask This Week

Sheila

You don't need my whole story to get the value of this, but you do need to know that the fear you may be feeling about something you've already done before probably isn't telling you what you think it's telling you. Sit with it this week and see what changes. Truly, I invite you to find one place this week where fear is showing up around something you've technically already proven you can do and ask yourself honestly whether it's about capability or about a structure that isn't there anymore. Thank you for listening. I hope you have a beautiful rest of your week, and I will see you on the next episode.