Why courage matters more than confidence

This is the final piece in my three-part series on navigating career transformation with clarity, curiosity, and courage. If you missed the earlier parts, start with clarity and curiosity.

Most people wait to feel confident before making a big career move. They want to feel certain they're capable, worthy, ready. So they take another course, read another book, do more research, and then, most often find themselves exactly where they started – knowing more but feeling no more ready than before.

But while confidence is a belief, courage is a choice. You can't always believe in your abilities especially when you are feeling confused or sensitive, but you can make the choice to act anyway. Each time you choose courage, you create proof of your capability. Every action becomes evidence that you can handle uncertainty and do hard things even when you don’t feel ready. 

If you're waiting to feel confident before making your move, you might have to reframe how you think about confidence. Courage comes first and confidence is what you build along the way through repeated actions.

Career change invites reflection and deep analysis, but too much time in your head can become a trap. There are two ways to get stuck in thought, and both keep you from moving forward.

The first is overthinking. You take the same thoughts and turn them over until they split into a hundred smaller questions. Should I stay in this company or go? What if I make the wrong choice? What if I regret it later? What if this is actually better than I think it is? The analysis becomes so overwhelming that doing nothing at all feels like the safest option.

The second way you get stuck in your head is daydreaming. You imagine a happier life, picture yourself doing something else entirely, working on things you actually care about, spending your time in ways that fill you up with energy and inspiration. Daydreaming makes you feel creative, expansive, and hopeful, but it also keeps you from action as you dismiss those aspirations as unachievable, or just dreams.

Both daydreaming and overthinking have their place. You need to connect to those deeper desires and be true to yourself about what a meaningful life could look like, and you want to be anchored in reality and make plans based on what you need. But at some point, you have to move from thinking to doing, because when you stay in your head too long, both overthinking and daydreaming start to feed the same thing: fear.

Perfectionism is one of the biggest blockers. As Thomas Curran writes in his book The Perfection Trap, perfectionism lives in our interiors via a lingering and unshakable insecurity about what we don't have, how we don't look and what we haven't achieved. 

The perfectionist mindset tells us that we need to wait until we've figured everything out. But "I need to prepare more" is usually just fear in disguise. You're scared to put yourself out there, so you keep preparing as an excuse not to act.

Then there's the sunk cost fallacy, the idea that you should continue investing in something because you've already invested so much, even when it no longer serves you. Economists will tell you this is irrational thinking. The time, money, and energy you've already spent are gone whether things stay the same or they change. What matters is what you want moving forward and whether your current path will get you there.

The sunk cost fallacy almost got me. I spent over a decade working in startups, building skills, a network, and a career trajectory that made sense to everyone around me. The logical move would have been to keep going and leverage what I'd already built. But I didn't want to keep going. Just because I'd invested years into something didn't mean I had to keep doing it when it stopped feeling right. Those years weren't wasted, I still use what I learned and my network continues to support me, so what I have built over the years is helping me grow in my current phase.

There's also the fear that you're too old to start over, which needs no explanation. You are never too late to start building the life that you want. There are plenty of examples of people who found success later in life. Take Nobel and Pulitzer Prize-winning author Toni Morrison, who wrote her first novel, "The Bluest Eye," at age 40, while she was working at Random House as an editor. She won her Pulitzer Prize when she was 56, and her Nobel Prize in Literature at 62.

These are all stories we tell ourselves to avoid the discomfort of change. They feel true because change is scary, but that doesn't make them accurate.

I love this quote from writer Anaïs Nin: life shrinks or expands in proportion to one's courage.

When you make space for courage in your life, you open yourself to growth, new experiences, and opportunities that weren't available when you were playing it safe.

In my work with clients, I've seen how this actually unfolds in the context of career change. It starts with admitting you're unhappy or telling someone you're thinking about a change. 

Then you take bigger swings: you tell your manager you want to focus on a specific project and work towards a promotion this quarter, you ask for the raise you've been wanting for a long time, you reach out to people whose work resonates with you and ask if they'll talk to you about their path. 

Eventually, you're ready for moves that once felt impossible—leaving your job to start your own business, going back to university to study what you've always wanted to, building the creative project you've had on your mind for years.

And while the path looks different for everyone, the common thread is this: acts of courage compound.

You start with something that feels manageable, prove to yourself you can act despite fear and discomfort, and that fuels your next attempt.

Your self image shifts from ‘I am someone who gets stuck in fear’ to ‘I am someone who acts despite it’.

Over time, what felt impossible comes within reach because you've trained yourself to move forward without feeling fully prepared. This is how you build real confidence, not by waiting to feel ready, but by acting and letting the evidence accumulate.

Anne-Laure Le Cunff talks about this approach in her book Tiny Experiments. Instead of committing to massive changes or announcing a new identity, commit to learning through small experiments. 

Pick something that scares you a little, something you've been avoiding. Decide on a short timeframe, maybe a week or two and do the thing. 

Notice what happens, pay attention to how it feels and what you learn, then decide what to do next based on what you actually learned rather than what you feared might happen.

What I like about this experimental approach is that you can frame everything you do as a learning opportunity, rather than success or failure, and this removes the pressure of needing to get it right.

Nobody can build courage on your behalf. You have to do it yourself, one action at a time. But having support and structure makes the process far less overwhelming. 

If you're ready to move from thinking about change to actually making it happen, I work with clients over three months through the pillars of clarity, curiosity, and courage. We create a roadmap together that turns your intentions into momentum. If you’d like to explore working together, schedule a free discovery call.