What No One Tells You About "Betting On Yourself"

On paper, “betting on yourself” sounds exciting.

It even gets romanticised.

It’s the story we love to hear, of someone leaving the safety of the known, going all-in on their dream, and coming out on top.

Yet there’s a big part that gets left out.

When you bet on yourself, you’re also holding all the risk, all the responsibility, and all the uncertainty. There’s no safety net to catch you. No boss to shield you. No one to pick up the pieces if things go wrong. It’s completely on you to figure everything out.

If it works out, then the win is yours. If it fails, so is the loss.

With that, comes a weight of pressure you can’t just take off.

A weight that doesn’t just exist in your mind, you feel it in your body.

And some days, it can feel like a lot to carry.

When betting on yourself feels heavy

This morning, I woke up in a mental fog.

A few money pressures in the background. Work projects feeling a bit scattered. Some ulcers in my mouth from pushing things too hard and feeling a bit run down. And overall, not feeling my usual spark to attack the day.

It’s not the version of myself I like to show the world, but it’s the reality today.

And I think there’s something worth exploring here.

Because if you’ve ever tried to build something meaningful on your own, you’ve probably felt this too.

What it really means to bet on yourself

I first bet on myself at 23, when I decided to become a professional poker player.

No regular income. No savings account. No one to cover my rent if I had a bad month. Just me, my bankroll, and my ability to perform under pressure.

It was the ultimate gamble, not just with money, but with my identity. Every day at the table was a test of whether I could keep my cool, adapt to new challenges, and survive in a game that doesn’t care about your feelings.

At 29, I did it again. I walked away from the familiarity of poker to start a coaching business. I left behind something I was good at and understood, to step into something uncertain and unproven. I didn’t have a blueprint. I didn’t have a safety net. I just knew I couldn’t keep playing the same game forever.

And now, at 37, I feel like I’m standing at that edge again. This time, the leap is into sharing my ideas, my reflections, and what I find valuable with the world. Writing, creating, speaking — without hiding behind the safety of a niche. It’s exposing in a different way.

I don’t know how other people feel when they bet on themselves, but for me, it always comes with pressure. A weight in my chest that says, You have to make this work. That nobody’s coming to save me. That I can’t afford to drift for too long, to have too many off days, or to fall behind.

It’s a tension I’ve carried through each chapter of my life. Sometimes it fuels me. Sometimes it drains me. But it’s always there.

And maybe that’s the real cost of freedom.

The solitude of the solo path

Most days, I love it.

I love waking up and knowing I’m in charge of my day. I love walking into my office, making coffee, and sitting down for a morning of deep work. No one telling me what to do. No meetings I didn’t choose. No limits on what I can create.

That freedom is the reason I chose this path, but it’s also what makes it hard.

When you’re the only one in the room, there’s no colleagues checking in, no deadlines being chased by a group, no shared adrenaline before a launch. There’s just you, your thoughts, and your own willingness to move things forward.

Often, that’s empowering and I feel like the captain of my own ship, steering toward something I’ve chosen.

Other days, it’s like rowing alone in still water, just me and the oars, wondering if I’m still heading in the right direction.

Setting your own goals and deadlines

One of the challenges I often face, is that without a boss or colleagues, there’s no one to disappoint but myself.

On good days, that’s liberating — I get to set the vision, choose the priorities, and decide what matters most. But on the harder days, it means I’m also the only one holding myself accountable. When I’m tired or feeling off, it’s easy to move my own deadlines.

I can tell myself, I’ll get to it tomorrow. And in the moment, it feels harmless. But those small delays can quietly stack up, almost without me noticing. It’s not until I zoom out and look at the bigger picture that I realise the drift.

And that’s when the thought creeps in, that "I’m behind where I thought I’d be."

When the drive isn’t there

The truth is, no matter how much you love what you do, there will be days when the drive just isn’t there.

It doesn’t matter how big your vision is or how much freedom you’ve created for yourself. Some mornings you wake up, sit down at the desk, and feel like you’re dragging your feet through mud.

Motivation is seasonal, it comes and goes without warning.

There are weeks where I feel like I’m sprinting, ideas are pouring out of me and progress is building on itself like a snowball rolling down a hill. And then there are weeks like this, where everything feels slower, heavier, like I’m now pushing a boulder up a steep hill.

The temptation on days like this is to wait until you feel “ready” again. But I’ve learned that waiting can be dangerous. One slow day can turn into two. Two into a week. And suddenly, you’ve lost the momentum that took months to build.

The key I’ve found for me, is to show up enough on the low-energy days to keep the wheels turning. It might not be a breakthrough day. I might not feel inspired. But if I can move the needle, even slightly, I’m keeping myself in the game.

And that’s more important than anything else.

The illusion of falling behind

When my energy is low, it’s not just the work that slows down — my mind starts playing tricks on me.

I begin comparing where I am to where I thought I’d be by now. I think about other people moving faster, building bigger, achieving more. And it’s easy to convince myself that a quiet week means I’m somehow falling behind.

The problem is, that’s not reality, it’s just the story my mind tells when progress feels slower than I want it to be.

Zooming out always shows a different picture. One off day doesn’t erase the months of momentum behind me. One slow week doesn’t cancel out the consistency I’ve built over years. But in the moment, it’s easy to forget that.

It's easy to mistake a dip in energy for a decline in capability.

That’s why these stretches can be so dangerous, not because they actually derail you, but because they can make you believe you’re already off track. And when you believe that story, you start acting like it’s true.

For me, this is when I pile on extra stress and pressure that isn't helpful.

Re-anchoring to the big picture

When I strip away the noise, I know why I’m doing this.

It's not to tick boxes or endlessly chase performance metrics.

I'm here for three things:

• Growth: to keep evolving as a person.

• Connection: to share ideas and moments with people who resonate.

• Contribution: to leave something behind that matters.

These act as my compass. And days like today, when the weight feels heavier, are the exact days I need to remember them most. Because the truth is, these slower, messier days are a vital part of the journey.

They’re the resistance training of the creative path, the moments that build resilience and deepen my commitment.

When I look at it that way, I realise I’m not off track at all.

I’m just training a different muscle today.

Choosing the next step, not the perfect step

So what do you do on days like this?

I’ve found it’s best to stop trying to engineer the perfect plan or wait for the perfect mood. Instead, the goal is simply to choose the next step, and take it.

It might be small. It might not look like much from the outside. But if it’s aligned with where I want to go, it matters.

Today, for me, that step is writing these words. They may not be my most polished, but they’re the best I’ve got today. And they’re proof that I showed up. That I kept moving, even when it would’ve been easier to let the day slip away.

Later I’ll go to the gym and see what my body can do. I probably won’t hit any personal bests today, but I’ll get the reps in.

Then I’ll focus on recovery, get an early night, and be ready to get after it again tomorrow.

Anyone can start, few keep going when it’s heavy

Betting on yourself means carrying the full weight when things get rough.

Some days will feel light and full of momentum, others slow, heavy, and uncertain. The fog, the uncertainty, the pressure, the self-doubt — they’re all part of the deal.

This is what betting on yourself actually looks like.

It's not all big wins and perfect days. It’s taking full responsibility when no one’s watching, owning the quiet stretches, and staying in the game when it would be easier to quit.

I've realised that for myself, isn’t about having endless confidence or constant inspiration either.

It's about trusting the process enough to keep showing up, even when I don't feel like it. I know that if I can take one step forward on the days I feel at my worst, then I’m not falling behind at all.

I’m actually right on track.

Adam