Managing risk without losing direction

This week I am straight back into action after an incredible two weeks away on a goal-board trip to the Galapagos Islands in Ecuador.

Everything was incredible. We snorkelled with every fish I could imagine (even sharks!), watched sea lions sleep on every surface they could find, and saw both giant tortoises and baby sea turtles. Add in the 7-hour time difference and lack of Wi-Fi, and it became the forced complete switch-off I didn’t realise I so desperately needed.

To get to Ecuador, and then the various islands, we flew a lot. Mostly on smaller planes and often in unpredictable weather (we were pretty lucky with it but naturally still saw a couple of storms).

One of the small propellor planes we flew on!

Some flights were in full sunshine. Some in pouring rain or thick cloud.

We had two flight delays due to storms.

And as a personal first for me, one flight even had an aborted landing just metres above the runway, where they climbed back up, circled, and came back down for a smoother second try.

I slightly lied about the complete switch-off from work, because on the latter flight in particular, I found myself thinking how this is exactly what running a business feels like.

We’re all flying in different weather.

Sometimes it’s calm, sometimes it’s chaotic. Sometimes you can see miles ahead, but other times, I for one feel like I’m just having to trust my gut with what risks to take and when.

Turbulence is a certainty in both flying a plane and running a business. So rather than telling yourself you can avoid those patches altogether, it’s really all down to how you manage the risks that come along.

With the art of flying through uncertainty, there’s a difference between taking a risk and understanding risk. The founders who grow sustainably are the ones who know when a cloudy patch is just clouds, that will be worth it to get closer to the final destination, or when they’re hiding a mountain you could crash into.

Pilots will know what’s on the other side of a cloudy patch.

When I now work with founders who want to launch something new, be that a service, a pivot, or a rebrand, there’s often hesitation. Not because they lack the ideas or the ability to execute, but because they don’t yet know how to assess the risk in front of them.

Conversely, in one of my past corporate world jobs as a Design Manager, part of my role was to prioritise the different ideas we had from the business to grow our digital channels and build our strategy and 5-year roadmap accordingly. There’d be plenty of big asks that came through with no risk consideration, just an idea that someone was personally invested in and big financial backing from their department. We’d call these the “JFDI’s” (just f-ing do it requests), so it became a whole new part of my job to explain why we probably shouldn’t. They were at the opposite end of the spectrum from underestimating the risk.

So rather than trying to become “braver,” I want to invite you to become better at assessing the flight conditions.

I’ve been reflecting on the core questions I use, with both myself and my clients, to manage risk in a more grounded and strategic way. So if you’re considering change, this is for you.

The reward

Every risk carries a possible reward, but we rarely stop to define what that actually is. Too often, founders try to define that reward as something vaguely optimistic, like “it could really grow the business” or “it might attract new clients”, but when you’re evaluating risk, you need to get specific.

What would success look like, not just for you, but for your customer?

What’s the tangible reward for taking this leap, and does it connect to what you actually want for your business long-term?

For example, a creative coach once told me she wanted to launch a group programme. On the surface, it seemed a smart idea that was scalable and could have a greater impact per her hour. But when we unpacked her motivations, she realised the real reward she wanted was deeper relationships, not more people. Scaling down, not up. The risk of launching this new service wasn’t worth it, because the reward didn’t match the outcome she actually wanted. It wasn’t going to get her closer to her future goal, and likely could’ve ended up being something she resented doing.

When you clarify the real reward, for your customers, your business, and your future self, you immediately see whether the risk is worth flying through.

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The scale

Not all risks have to be all-or-nothing.

Sometimes you can’t see what’s beyond the clouds because you haven’t climbed high enough.

But you can sometimes test the journey first. (Am I pushing the plane analogy too far yet? I will keep going).

If you’re launching a new service, can you offer it as a limited beta to a handful of existing clients?

If you’re planning a new course, can you test one module or a related workshop first to see if people respond?

If you’re developing a product, can you order a small run before committing to stock? Or launch in one colour way rather than your planned three?

The same principle applies internally. Before overhauling your entire website, test a new messaging direction on social. Before hiring a team, trial a freelancer or automation to see what support you actually need.

There are so many different services I myself have had ideas for. I easily could’ve jumped straight into trying to launch them all, but over the years I’ve instead trialled launching a related freebie, beta service, or even just posting an IG story poll to get some feedback. Some of the ideas I thought were my absolute best were instead met with crickets. Which might have been a bit of a blow at the time, but also a complete relief that I hadn’t poured even more energy into something that wasn’t going to pay off.

Yesterday I was on a strategy call and used the analogy of a skydive (apparently I’m really loving the whole flight thing at the moment). In my first and only skydive, I was supposed to jump from 12,000 feet. But there was a thicker sheet of cloud that the expert physically attached to me said we shouldn’t jump through, as he wasn’t confident about what was on the other side. So we went slightly lower and jumped from 10,000 feet instead. This was a blessing for many reasons, primarily because I was the most scared I’ve ever been, but also because we could then see the landing site clearly. (Or at least he could. My eyes were shut).

Proof that I did complete a skydive and my eyes slightly opened once the parachute was open!

The lesson wasn’t to abandon something completely when you can’t predict how it will turn out, but to adjust your plan. Do it in a slightly different way or launch it in a somewhat smaller scale at first to reduce the risk.

I still did the skydive, but we managed the risk accordingly and just did it at a slightly lower height.

The cost of standing still

We often frame risk as a threat. But staying still is also a risk we can underestimate.

Especially in today’s climate, markets are evolving and customer expectations are changing at a rate never before seen. If you never take a calculated risk, you risk irrelevance.

The key is to evaluate both sides of the equation: what happens if you do this, and what happens if you don’t?

For instance, a photographer I worked with kept delaying a price increase because they feared losing clients. We worked through their different service package mix and the maximum amount of money they’d be able to make each quarter, rolled up to yearly, with their current prices, and their business simply wasn’t sustainable. The risk of staying the same was greater than the risk of raising prices.

It took only a few months after them increasing their rates and re-designing their website to show up as the higher-value photographer their skills were reflective of, before they were attracting more aligned clients and stabilising their income.

Sometimes the fear of change masks the cost of inertia.

So zoom out, and ask yourself what’s the risk of continuing to fly the same route when the weather’s already changing?

Are you risking never getting to a new destination?

The goal

Every risk is, in essence, an experiment in achieving a goal. But sometimes, we fixate on the method rather than the mission.

Businesses take a lot of time to become ‘successful’, and in that time, it’s easy to lose sight of the north star you’re supposed to be aiming for.

I frequently see this with founders who come to me thinking they need a huge new offer or a rebrand to grow. But often, they’ve lost sight of the true goal of their business. No longer knowing what they’re actually trying to achieve, meaning they can’t evaluate if their shiny new idea is the best way to do it.

Going back to the creative coach I worked with, they’d told themselves their goal was to reach more people, and felt that launching a group programme was the best way to do that. However, when we delved deeper into their strategy, we discovered that what they truly wanted from their business was to establish deeper relationships with higher-value clients. Launching a group programme isn’t going to get them any closer to that.

Instead, it turned out to be more of a re-positioning piece. Redefining themselves in their coaching market and honing in on their real target customer, with messaging and a website that helped them to align with this person.

This is where I bring in my ROOTS framework. Whenever you work with me on your business strategy, we go deeper into your business to make sure you can confidently answer these. But these are the five core questions I encourage you to ask yourself before making any major decision:

• Relevance: Does this resonate with my current audience and market?

• On-brand: Does it reflect my identity and positioning?

• Outcome-focused: Will it drive the change I want?

• True: Is it authentic to me and my values?

• Sustainable: Can I deliver it well over time?

If you can honestly say yes to all five, you’re in safe flying conditions. If not, you might need to adjust your course before takeoff.

Set your business up for safe flight conditions.

The sustainability

The sustainability of an idea is often the area that’s most overlooked, and subsequently, the biggest reason for failure.

Even if an idea works, it’s not a success if you can’t sustain it.

A one-off marketing campaign, for example, might require an intense push but then it’s done.

Starting a newsletter, on the other hand, demands weekly consistency. Launching a course means ongoing support, feedback, updates. Hiring a team means management, communication, payroll.

None of these are “wrong”, but each carries a different kind of risk that needs to be evaluated.

We’re often so quick to consider the monetary cost of an idea without evaluating the cost of lost time, energy, attention, or alignment. When the latter can be much more detrimental.

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I recently caught up with another freelance friend who launched a digital product with the goal of generating passive income. They’d put on their sales page that they’d provide feedback on the completion of this product, thinking it would be a nice way to make it more worthwhile and that this could start conversations with people who could be converted into clients. Except they’ve found themselves answering daily support questions, taking calls with people who they quickly realise have no intention of paying for their services, and ultimately losing time they could be spending on paid work.

If something can’t genuinely be maintained without compromising your focus elsewhere, that’s a big risk to take.

Rather than only assessing if something will work, make sure you evaluate the cost of it working out. If it is a success, is that success sustainable?

Managing risk through your business design

Managing risk is ultimately a design choice. The goal should always be to design your business in a way that naturally absorbs uncertainty. Where you know how to make decisions, assess opportunities, and stay ahead of the constant weather changes.

That’s what I help founders do inside the Business Blueprint: define their direction, purpose, and positioning so every future decision can be filtered through clarity.

But if you’re not looking for a full strategy session yet, here’s how you can start building that resilience yourself:

1. Define your north star.

Know what you’re working towards and what “success” looks like for you. When you know the destination, it’s easier to decide which risks are worth taking.

2. Understand your customer deeply.

If you understand their genuine needs, fears, and desires, you can determine which ideas will truly resonate with them.

3. Know what success looks like.

Picture everything going perfectly, and then reflect on where that will take you in 5 years. Is that a place you want yourself and your business to be in? Is it sustainable, both financially and emotionally?

4. Build feedback loops.

Don’t fly blind. Gather customer feedback, track results, and adjust early and frequently.

5. Treat failure as data.

Not every attempt will land smoothly and that’s fine. Sometimes you might need to abort the landing so you can learn and try for a smoother attempt the second time.

Back on that small island runway, after the aborted landing, I remember the quiet on the plane. We all shared glances at each other and nobody spoke for a few seconds as we were quickly climbing back up into the air. Then the pilot came over the speaker, calm and clear, to tell us it was “not possible to land yet, but everything is fine. We’ll be doing a loop and then landing again.”

That’s all it took. There was then no panic or drama, just an informed decision.

Running a business will always involve uncertainty. But you can train yourself to read the signs, adjust your altitude, and decide which risks are worth taking.

The goal isn’t to avoid turbulence. It’s to build confidence that you can fly through it.

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And if you need help, let’s work together!