When (and How) to Take Big Risks

This article is a summary of our Designing Tomorrow podcast, Season 2 - Episode 14. Season 2 episodes are conversations between Jonathan Hicken, Executive Director of the Seymour Marine Discovery Center, and Cosmic’s Creative Director, Eric Ressler. 

Taking risks can feel like a high-stakes game, especially when it comes to leadership in social impact organizations. But sometimes, the most significant growth opportunities come from the biggest bets. In this article, we explore when and how to take calculated risks in a business context, along with tips and reflections on how these choices can drive success.

The Personal Connection to Risk

It’s easy to shy away from risks, especially when the stakes are high. Let’s say you’ve recently taken up mountain biking after living in a world-renowned mountain biking area for nearly 15 years. One day, as you're navigating a particularly tricky section of the trail, you find yourself sitting at the top of a large rock, unsure of how to proceed. In that moment, you ask yourself: What’s the worst that could happen?

On one hand, if you successfully made it down the rock, you’ll feel accomplished. But on the other hand, a serious fall could set you back in terms of your personal life, health, and work. Ultimately — you decide to walk around the obstacle. There are some parallels here about taking risks in a business setting, particularly in social impact organizations, and when and how to approach those decisions. At Cosmic, some of our most important growth points have happened when we have taken a big swing, a big risk, or a big bet.

Risk in the Social Impact Sector

The social impact sector is not really known for being very risk-taking. Unlike the venture capital world, where failure is expected in the pursuit of one big success, social impact organizations often operate under tight budgets and the pressure to create immediate results. However, there are plenty of examples of moonshot initiatives within the sector that have paid off, proving that calculated risks can lead to exceptional outcomes.

In the venture capital world or the startup world, venture capitalists and startups know that nine out of 10 of their startups and ideas are going to fail. But they also know that probably one out of 10 are going to be wildly successful, and they do that calculation and they realize that it is going to pay off. There's a lot of discussion in this space around moonshots and these big bets versus just funding things that are already proven. 

Assessing Risk

But how do you know when and how to take risks in a calculated and constructive way for your organization? How can we develop a framework or a thought process or even just more of an intuition around how you might do this?

We think about risk-taking every single day. The way we define risk is the highest upside, knowing that there may be some potential, not just neutral results, but some negative results. We constantly look for the highest upside, the highest leverage activities to deepen our impact or to create a more financially sustainable organization.

Risks can come in all sorts of shapes and sizes. It can be new programs, new revenue streams, all the way down to putting out a new formatted email newsletter or trying a new line of pitching a membership to the people that are walking through our front door. Ultimately, it's about where the leverage is, where the upside is, and how that compares to the risk.

In some of the bigger risks that we've taken Cosmic, we tried to think about how we make those decisions and how we knew it was time to make those decisions. For many social impact leaders, this is something they've built over time as an instinct or a gut-level choice in certain ways. 

Build Risk-Taking ‘Muscle’ by Starting Small

Our risks started really small. In the early days of Cosmic, Eric, our founder, was working out of his bedroom. He was renting a house with a bunch of friends who were working restaurant jobs, and he was finding it hard to concentrate during the day when they were off work trying to get him to go surf and ride his bike. He was trying to get work done, and I realized, "Hey, this is not sustainable." 

He needed to come up with some kind of way to have some private, focused space. At the time, he saw an opportunity to get an office — it was actually just a desk in a co-working space. That was a very big risk for him because he had very little income. He was already struggling to pay rent. This was just added expense. But he knew that what he was doing was not sustainable, so he took that risk. 

That is probably the absolute best decision he’s made in his entire life because that led to so many opportunities and networking and really supercharged the business and made it what it is today. At the time, it was risky. But looking at the downsides, what he was doing was not sustainable. It was almost like a forced function that led to a risky choice.

The Time Will Come to Take a Big Swing

After about seven years of running Cosmic, we decided to focus only on social impact work, what we're doing today, and that was a very, very risky decision. But at the same time, we were in another kind of forced function where we were stalling out. We were not making progress financially. We were not making progress creatively, and we knew that we needed to change something — that needed to be something big. 

Luckily, we had some great advisors to help us with our positioning. We explored a lot of different things, and we mitigated that risk through research and through discussions with advisors. So we didn't just blindly take that leap of faith. We spent time looking at how we could de-risk this risky thing but still place a really big bet.

How to Think About Risk

If you're going to take a big risk, here are some tips to make sure that you're more likely to have that risk pay off and not fail.

1. Go Full Send

One thing we've learned about risk-taking as it relates to risky sports like surfing, climbing, and mountain biking that ‘s also very relevant to business, is that you've got to go full send. If you are going to take a risk, you cannot hesitate. The times many people get the most injured doing any of these sports is when they've hesitated. If you are getting tired and you're climbing and you do a move and you're not really quite prepared to fully commit, that's when things go wrong. 

That's also true if you're going to take a big swing or a big bet or make some kind of risky move. You've got to fully commit to that move, or that actually becomes more risky in the long term.

Bailing from a risk can actually produce really bad outcomes, especially in a business setting. If you're constructing a major pivot for your social impact organization and you've got a lot of the pieces in place and you start to roll out the new messaging or the new imagery or the new products, and you back off from that after a certain level of commitment, your audience may start to wonder what's going on there. It may start to lose trust. 

There is a real corollary in the social impact space to the sports one where if you're going to take a risk and you really want to go for it — you really have to go for it.

2. Be Clear on the Goals and Outcomes

If you're going to take a risk, you have to make sure that you're clear on the goals and the outcomes. Why are you taking this risk and what are you hoping to achieve through taking the risk? If you don't have that clear, first of all, you don't know how to prepare for the risk. You don't know how to de-risk it, and you don't know if the risk is paying off. So as much as this is an exercise in intuition, you still have to be able to tie the outcomes and the goals back with objective metrics or some kind of evaluation.

3. Communicate Clearly

If you are going to take a really large risk at your organization as an executive director or any kind of leader, one of the things that is absolutely critical is to be very clear with your communication with the rest of your team around why we are taking this risk and what you are hoping to achieve by taking this risk. 

Acknowledge that, "Hey, this is a risky thing that we're doing. This is a big bet that we're placing, but we're going to do it and we're going to fully commit to it. And here's why." 

Because if you don't do that and you do all that calculating in your brain or just silo that just to the leadership team, but you don't communicate that to your broader group of stakeholders or even your community, people might start to wonder what's going on. Clarity and communication are actually really important in any of these big moves.

4. Be Willing to Fail

If you're planning on taking a big risk or placing a big bet, you have to be willing to fail. You have to be willing to accept failure as not being a failure, but being part of the process of being risky and taking big risks and placing big bets. You have to be willing to learn from your failures and not take them too personally. Now, if all of your risks are failing, that is a signal that you are maybe not being very intentional or strategic with your risks, or maybe you're just not very good at the risks that you're taking, and you should recalibrate from there. 

But you have to be willing to write it off and move on and continue to move forward if some of your bigger swings don't end up paying off.

Developing the Risk-Taking Skill

Risk-taking is a skill that can be developed over time. This isn't a natural trait where people are born as risk-takers or not.

Start small. If you struggle with taking big risks, change up something about how you work or show up. Start with smaller risks that feel big to you and develop comfort there.

It's important to acknowledge that some risks require life circumstances and privilege that allow for them. A crucial piece of risk calculation is asking who will potentially carry the burden of failure. If it's just you and something you can handle, that's one thing. But it's unfair to place the burden of failure on someone else, especially if they haven't bought into those consequences. As you ramp up the size or significance of risks, it's really important to ask these questions.

The Perception of Failure

The perception of what failure looks like is often much larger than what failure actually looks like. Sometimes, in the fear and the uncertainty of what could go wrong, we build up and overplay it in our heads. 

When something even does fail, you realize, "Oh, that wasn't all that big of a deal. I was able to get through that." You're more resilient than you think you are when it comes to taking these risks and failing.. You’re more resilient than you think, and your ability to recover from setbacks can be a powerful force for growth.

In the social impact space, where failure can feel especially consequential, it’s essential to reframe failure as a part of the process rather than something to avoid at all costs. Sometimes, not taking a risk is the greatest risk of all.

People think playing it safe is safe, but playing it safe is often very risky, especially when building a brand, doing marketing, and investing in the things that help organizations stand out. You have to be bold and risky to break through and stand out as a brand today.

Maybe you're riskier with branding and marketing but not as risky with hiring or evaluating impact and other mission-critical areas. Where you apply risk has big influence on how risky you should be.

The social impact sector should be riskier in general, with a more constructive and healthy culture around failure. Not to the extent of the startup world where things get overly inflated and propped up by investors looking for 10x returns — that can go too far. But there should be more culture around embracing building in public, failure, and not seeing failure as failure.

The Risk of Inaction

When it comes to risk-taking, sometimes not making a decision is itself a risk. Maybe the world is changing around you, or the problem you're addressing is changing, or your audience is changing. Something is changing. 

Meet the Moment. Take a Big Swing.

Risk-taking in social impact work isn't about being reckless or chasing venture capital-style moonshots. It's about being strategic, communicative, and fully committed to the calculated bets that can transform your organization's impact and sustainability.

Risk-taking is essential for growth, innovation, and success, especially in social impact organizations. But knowing when and how to take risks requires careful consideration, clear goals, and a willingness to embrace failure. As you plan your next big move, remember that the biggest risk may be playing it too safe in a world that demands bold action from those working to solve our most pressing challenges.