(Re)building the courage to take risks in your thirties

On making bold moves when you have more to lose

According to psychologists, the world is made up of two types of decision-makers: the satisficers and the maximisers.

If you’re a satisficer, you make decisions swiftly and rationally, objectively calculating the pros and cons, then choosing the path that neatly slots into your logic-based criteria.

But for the maximisers—oh, if only life were that easy. Maximisers want to make the best decision they possibly can. They don’t just weigh up the pros and cons in front of them, but think about how the decision will affect them in the future.

Will they wake up in a cold sweat tonight, having opted for an oat flat white over an iced matcha latte? 80 years from now, rasping on their deathbed, will they wring their hands because they didn’t buy those shoes?

Unsurprisingly, maximisers may struggle with regret—dwelling on the roads not travelled, plagued by a sense of failure at not having met their (probably impossibly high) standards.

The fact that I named my coaching business More To Life and this Substack Messy Work will give you an indicator into which camp I fall (the agonising one).

The mess

According to Google AI (a fountain of wisdom), maximisers can be characterised by:

• Taking a lot of time to make decisions, or even suffering from decision paralysis

• Experiencing more regret and dissatisfaction with their choices

• Comparing themselves to others

• Being perfectionists

• Reporting lower levels of happiness and self-esteem

Whereas satisficers:

• Make decisions quickly

• Are more content with their choices

• Are less reliant on other people’s opinions and external validation

• Settle for “good enough”

• Trust their gut

I’ve been reflecting on this dichotomy in the context of risk, which—as I shared in my last post—has been on my mind lately.

Being in your late twenties or early thirties is a time that’s filled (and often fraught) with change. A time where we shed old skins and become all over again. A time when we are presented with big decisions, all of which carry an inherent risk, sacrifice or compromise—whether we are prioritising growth over familiarity, or finally succumbing to stability and security.

Yet I’m noticing (from my own, my peers’ and my clients’ experiences) that, in a cruel twist of fate, all this decision-making can coincide with a waning tolerance for risk. Put simply, we are not as young, carefree and fearless (and perhaps, naive) as we used to be.

Having conducted extensive and statistically sound research (lol), I can report that 100% of voters in my poll agreed that their risk tolerance had changed with age:

“When I was 18, I took off for a summer alone in Germany for language practice and didn’t think anything of it. Now, I’m in two minds about booking a week’s solo holiday!”

“I have absolutely felt some hesitancy creep in! And it's almost like I don't recognize myself.”

“Hard relate to this! No problem moving country and starting a new job (especially when I was younger), but why do risks taken with the heart feel the scariest?!”

Make it make sense

I wrote about this in my first ever Substack post, but a combination of factors can influence our aversion to risk as we age:

1. Our own life experiences - It makes sense that the more storms and knocks we weather, the more cautious or even cynical we may become. Of course, the inverse can also be true—sometimes, the beauty of heartbreak or loss is that it makes you brave, leaving you wide open to whatever changes or opportunities come your way.

2. The structure of our brains - As we age, grey matter shrinks in certain parts of our brains, which has been linked to increased risk aversion.

3. Global crises, natural disasters, silly men, etc. - to quote my previous post:

At this specific moment in time, the world is a very uncertain place. According to the Financial Times, “over the past 60 years the west has begun to shift away from the culture of progress, and towards one of caution, worry and risk-aversion”. So perhaps it’s not just biology at play; we’ve become existentially risk-averse.

Again, this makes sense: our comfort zones offer us protection. And there are times in our lives when we really need to prioritise that (like a global pandemic).

In 2020, after the loss of my dad to COVID, a lockdown and a two-year stint in a stressful job, I had to unlearn a lot of my Type A habits and consciously not try, giving myself the time and space to heal.

4. The feeling that we have more to lose - this is an interesting one, as I think it can be both a truth (for example, when you have bought a house, committed to a relationship, or are responsible for someone else’s wellbeing) and an illusion (when it comes to things like reputation, pride or the permanence of our decisions).

What then, is a thirty-something (or sixty-something) who’s feeling a bit stuck or dissatisfied, but increasingly risk-averse, to do? It leaves us with a lot of big questions to work through.

Firstly, how do we know what we really want?

Secondly, if we decide to go after it, how can we be sure it will be worth the risk?

And thirdly, how can we find the courage to take that risk?

The work

Call me defensive, but I think Google AI’s take on satisficers vs maximisers paints too crude a picture of aspirational decision-making.

I think there are lots of advantages to being a maximiser: curiosity, thoughtfulness, strong research skills (we’re the friend who always knows the best place to eat/drink/shop/take a naked laughing aerial yoga class), self-awareness, and a commitment to making this one life as good as possible.

Maybe, we maximisers are actually better at taking risks—driven by that conviction that there’s always more to life, we’ll take bigger gambles (even if it takes a while to get there).

But, especially as we age and our identities take on new meanings, perhaps we need a little more help reconnecting to that courage. So how do we answer those questions?

1. How to work out what you really, really want.

I’m almost certain I have used this GIF before

They say that envy is a good indicator of what you really want. And to a point, I agree. That professional nemesis you love to bitch about? Maybe they’re just living out your fantasy.

But I think envy gets a bit more misleading in our thirties—a time that’s rife with grass-is-greener moments. All around us, our peers are taking different paths. Showing us all the different people we could be.

A dog owner, home renovator, spouse, or parent, giving into domestic bliss and gentle, rhythmic security. An adventurer, a traveller, an expat, swapping London’s grey skies for broad European boulevards, arid deserts, or palm-tree-lined islands. An freelancer, an entrepreneur, a founder, saying hell no to corporate life and working on your own terms. A winemaker, a writer, an artist, a therapist, retraining to do something with purpose, or finally pursuing our life’s dream.

When we’re presented with all these options, it’s hard to know whether these pangs of wanting will lead us to truth, or an illusion. Whether there is something deeper calling you, or whether actually, you’re content just as you are—because there’s nothing wrong with living a calm, steady life. Or a changeable, spontaneous life.

We’re fed so many messages about how to create meaning in our lives, but often it boils down to the small things—the interaction with the barista that kicks off our day, or the phone call with the friend who just gets us.

So how do we know what will really make us happy? How do we separate our own dreams and desires from what we’ve internalised?

In my coaching practice, I like to say that there’s no magic formula—all we can do is get clear on our foundations. And there are tonnes of helpful exercises you can do on things like values, strengths, vision-setting, or temperament.

But something I come back to a lot in life, which I think is so helpful in various contexts, is learning the difference (and the dance) between instinct and intuition.

What I mean by this is that instinct tends to be a physical, animal reaction—our nervous system telling us fight, flee, fawn, or freeze. Whereas intuition operates on a soul, spiritual, or core Self level.

Both give us important data about the right move to make. For example, I have been in many an anxious-avoidant relationship pattern when my through-the-roof anxiety was a good sign that this dynamic wasn’t working. But it was always my intuition that prevailed, and made me leave that relationship. In this situation, my instinct felt like anxiety and stress. But in the moments when I listened to my intuition, I felt calm, strong, and free.

I think if we can tap into that intuition, we won’t go too far wrong. Because when we follow that source of truth, there is no such thing as “failure”.

2. How to weigh up risks.

Of course, most of us can’t quit our well-paid jobs and potter around in a bookshop for the rest of our working lives (sigh).

While there’s a lot of discourse about bullshit jobs, finding your purpose, or even being consciously unemployed right now, much of the self-help/motivational content out there delicately sidesteps the issue of privilege and financial freedom, i.e. your ability to travel the world in an upcycled van depends on a variety of economic, cultural, and physical factors (and hey, no shade—I’m someone with the luxury to think about slow business).

So let’s take our head out of the idealistic self-development clouds for a second and think about your basic needs.

It might help to map this out either on the above pyramid, but what are the non-negotiable things that make you feel healthy, safe and supported?

For example, your home, your relationships, your pets, your gym membership. And what other higher needs might come into play? For example, one of your values may be independence, which you’re not willing to trade (see: half-joking fantasy to quit your job and become a tradwife).

And on the flip side, what are you prepared to risk? Failure? Pride? Now, this is where it gets interesting—where some of those things you think you’re not willing to risk are actually illusions. It’s time to probe your limiting beliefs.

3. How to pluck up the courage to take a risk.

I’ve a few coaching exercises up my sleeve here. One is to draw a series of concentric circles on a piece of paper, and map out your comfort zone, with activities or ideas you find really easy in the middle, and creeping degrees of scary in the outer layers.

It can be illuminating to see these things written down. Perhaps you notice themes and connections between the things that do or don’t terrify you—does your cautiousness show up in the financial, or the physical? Is there a recurring fear of being seen across each layer? And from here, how can you start to play with the limits of your comfort zone, practicing the art of risk one step at a time?

I also really loved this tool from Elise Loehnen’s Substack, Pulling The Thread, as a way to explore and challenge the inner critics/voices of doom that can hold us back (referred to here as ‘Part X’):

1. Close your eyes and think of something in the future that scares you, or that you’re worried might happen.

2. Write down the Part X predictions. Write down everything you expect to happen as a result of whatever it is that scares you.

3. In a couple of weeks, read your predictions to see if any of this stuff really happened.

4. Sometimes Part X will be right; often Part X will be wrong. The point is not to convince yourself to be certain that Part X is always wrong, but to reveal that you don’t know, and that Part X certainly doesn’t know, what’s going to happen.

Of course, this speaks to the reality that none of us have any control or certainty over what the future holds. That question, of how can we be sure a risk will be worth it, is one we can never answer—we just have to do it anyway.

But coaching psychology aside, I’ve realised one of the things that makes taking risks in our thirties so difficult is that we don’t always have role models to follow.

We see the big, magical transformations sold by coaches and “gurus”; the flashy, pinch-me success stories splashed across centrefolds. But not the hard slog or the gut-wrenching sacrifices—even the regrets or failures—behind-the-scenes.

Because of this, I’m toying with an idea for a new Substack series that lifts the lid on what it really means to take a big risk. So if you’ve got a personal story—whether you’ve sold all your possessions to go and live in a Buddhist monastery, or, like Piper Ratliff, decided it’s not for you—I’d love to feature you.

I haven’t been able to stop repeating everything in Victoria Ratliff’s Southern drawl since I started White Lotus Season 3, is it just me

Drop me a message, and I can share more.

In the meantime, what’s the smallest (or even biggest 😉) risk you could take today?

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About me + Messy Work

If you’re new here, it’s lovely to have you. I’m Lucia, a writer and coach trying to answer some big questions about whether there’s more to life—and celebrating the mess along the way.

If you’d like me to write to you every couple of weeks (ish), pop your email below and I’ll be in touch.