Risk can make anyone uneasy, but it's also your path to incredible growth. We've pinned seven potent techniques to sharpen your risk-management skills, helping you confidently play any hand life deals.
UPDATED: September 29, 2025
Find yourself avoiding risk? It may be blocking you from the very doorway to your biggest wins.
For many of us, the risks required to advance in our careers can spark anxiety and can become a major stumbling block. However, the more you develop your appetite for risk, the more confidently you'll navigate uncertainty and leverage calculated chances to hit your goals. As our founder, Jenny Just says:
“You have to take risks (risks with an S) and make bets sooner rather than later – not just because those bets might pay off, but because you won’t learn if you don’t.”
Ahead are seven tried-and-true strategic plays to boost your risk-management prowess.
1. Map Out Outcomes & Probabilities
The first step in commanding risk is understanding it. Minor risks, like buying a lottery ticket, can be mathematically analyzed to gauge their efficiency: What are the chances of winning, and what’s the potential payoff? If the expected return is below the cost to play, it's not a smart bet.
However, many risks aren’t so black and white. Perhaps you’re eyeing a cross-country move to realize your dream of living beachside. Such a massive shift in your social circle, living arrangements, and work life can feel jarring. Instead, try envisioning the end-state.
Consider the spectrum of possibilities: At the negative extreme, the new area could fall flat, requiring a costly, inconvenient move back. The best-case scenario? You thrive, living your best years with a tan and perfect beach wave hair. Then there’s the middle ground, where novelty and small improvements make the upheaval of your big move just worth it.
Economists and game theorists call this reverse induction. Poker and chess players routinely think about the simplified scenarios they want to reach at the end of the game, then make early moves that set them on that path. It’s about seeing the finish line before you even start the race.
2. Win, Even When You Lose
The best risks? Ones where coming close still feels like a victory. Negotiating your pay at work is a prime example. If you make a compelling case for your value, your boss might not give you everything you ask for, but they’ll likely increase your salary. That's a win.
If the risk has a binary outcome, reframe failure as a stepping stone. Applying to a selective graduate program can feel deflating if you think about wasted time if you don't get in. Instead, envision the future regret of never putting yourself out there. If rejected, you'll still grow, and you’ll certainly gain peace of mind from trying your best.
Top poker players use this strategy when bluffing. By semi-bluffing—choosing bluffs that could improve to a strong hand—players have multiple paths to success. A semi-bluff can either force an opponent to fold a currently winning hand, or potentially become the best hand later to win a large pot. It’s about turning "if" into "when."
3. Divide & Conquer Your Risks
Many intimidating risks can be sliced into smaller, more manageable steps. Thinking of a career switch? Start with coffee chats with peers who’ve made the leap. Then, build skills for a competitive resume. Interview for a new position before leaving your current job. Accept an offer that retains some familiarity—location, function, or industry—and make the full transition later when you're truly ready.
This risk segmentation doesn't just create an achievable to-do list. It can also serve as your strategic hedge, giving you an out if you discover early that the risk isn't worth it.
Poker players manage risk aversion by dividing their total capital into many smaller game entries. Each entry is a controlled, uncorrelated risk within their overall portfolio. While one instance might not work out, the law of averages suggests smart, repeated risks will trend toward a favorable result.
4. Talk it Through with Your Tribe
To get in the right mindset for risk-taking, lean on your trusted circle for a sanity check. If you're nervous about making a job switch, for example, consider asking a friend or mentor what they'd do. There’s immense reassurance in gathering diverse opinions. It’s easy to doubt yourself, but tough to doubt the collective wisdom of your group.
From hedge fund managers to poker pros, the best risk-takers stand on the shoulders of giants to gain decision confidence. Support systems are crucial for smart risk-taking, not just for strategy, but also to talk down any doubt that might surface.
5. Separate Your Self-Worth from the Outcome
It's human to tie your identity to achievements. But when risk results affect your self-worth, you're less likely to take those necessary future chances. Instead, detach yourself from the outcome. Evaluate your risk purely on whether it was a strategically sound move.
Poker teaches players to accept that some days, a win just isn’t in the cards. In tournaments, you might only win prize money around 15% of the time. Over the long run, results show your ability. But after a single loss, you learn that luck plays a hand, and you can focus on what was in your control: your decisions.
Let’s sketch a scenario: You’ve called in favors at work to present your product ideas to key stakeholders. Presentations can feel like extensions of yourself. But your pitch's result might hinge on many factors: stakeholders distracted by urgent issues, the right idea at the wrong company development stage, or even a presentation style that clashes with their preferences, despite charming others.
There's so much outside your control; beating yourself up over the results of a calculated, well-informed risk doesn't change the outcome or help inform how you approach future risks. Instead, approach it as an opportunity to advance your decision making skills. As long as you prepare your best, everything after that is simply part of the play.
6. Leverage Commitment Devices
Commitment devices are clever tools to give yourself extra incentive to pursue a desired risk. Want to ask your partner to move in? Give a friend your favorite accessory—AirPods, jewelry, a watch—and tell them not to return it until you’ve had the conversation.
Often, just knowing they'll need to explain their thought process is enough of a commitment device to course-correct their play. Many poker players fix mistakes by recording hands in a tracking database and reviewing footage with a peer. Common issues like impatience, passivity, or lack of focus can improve dramatically.
Commitment devices counterbalance irrationalities, sweetening the pot when you take risks. The beautiful thing about smart risks? Take enough of them, and you'll see the long-term benefits, rewiring your brain to instinctively embrace them.
7. Play Poker
The ultimate sandbox for experimenting with risk-aversion strategies is the poker table. Every decision involves evaluating the risk of betting chips against the reward of winning more. You’ll develop a keen eye for when opponents are bluffing or holding a strong hand, then decide if you should bluff them back. Poker touches every facet of risk evaluation, from capital allocation to acting under uncertainty.
Your Strategic Uprising
We've laid out the plays, now it's your turn to ante up. Consider these risk intelligence strategies your blueprint for and embracing calculated chances like a true strategist. It’s time to bet big on yourself and claim your power, both at the table and in life.