Ahead of my appearance at the risk-taking lunch club for Rachel’s List with the awesome Monica Davidson from Creative Plus Business (insert fangrrl sounds here), I’m getting my nerd on and deconstructing my relationship to risk, how I get ready to take a risk, and how I keep my nerve steady in the moment.
This is how I get ready for risk-taking and what I do to prepare
Planning to take a risk
Taking a calculated risk is different from running up to the world with Muppet arms flailing. This is where planning comes in.
You don’t have to do a lot of planning to ground an idea or calculate if it’s a risk worth taking.
Two one-page models I use all the time are:
- BOER – Background, Objectives, Execution, Result
This overview helps me figure out what I’ve observed, want to change, how to do it, and what I predict or want the outcome to be.
- WOOP – Wish, Outcomes, Obstacles, Plan
This evidence-based model helps articulate all kinds of change. It includes a contingency and easily scales from daily planning to quarterly.
Making some mindset choices
Believe me when I say:
A risk needs to be inspiring
If you don’t believe in it, your audience have no hope. Joy, curiosity, a yearning for change, excitement, well channelled anger or frustration, something emotionally charged and fuelling the process must exist for a risk to be worth taking.
Accept it is an experiment
All risk is an experiment or a practical test of a hypothesis, not your next destiny. Keep it light, lean, and emotion-free. Overattachment leads to sinking copious amounts of time, money, and labour. And that makes it too hard to walk away.
Use what you’ve got
Waiting for the right time, a big bank account, a cast of thousands, some major educational shift, all the dominoes to line up – this isn’t risk-taking. It’s an excuse for inaction. Scale your idea to match your position right now – and plan expansion with more resources, budget, talent, etc if the beta stage is successful.
Move your arse
Risks and change are pretty time sensitive processes. If you labour too long, someone else will have spotted the same hole in the market and decided to fill it. The pace should also be part of what keeps you accountable to the process.
Find other risk-tolerant creators
Sadly, a lot of people are risk averse. Seeing you change or take a risk can frighten the crap out of them.
As Seth Godin explains, people are “looking for an easy way to keep things the same. They’re uncomfortable with the tension change brings and will conceal that fear with objections that feel like thoughtful feedback. It’s not.”
You need risk-tolerant connections to inspire you.
Risk-tolerant people:
- Have a balanced perspective. If you are a fan of Myers-Briggs, think people who are in the centre or on the Perceptive side of the scale (as opposed to Judging)
- Are adaptable and flexible. You might grumble, but you’re OK to adjust your sails and move the idea or attitudes to match prevailing conditions
- Mix optimism with the practical. Anything is possible with the right planning and action
- Welcome experimentation. It is OK to leave refinement for another day because you’re learning by getting the idea out there
- Aren’t afraid of failure. Nobody wishes for failure, but risk-tolerant people don’t freeze at the possibility. And after a brief recovery, can usually view failure as the price of growing and shipping things
Even if you need to work at it yourself, working alongside risk-tolerant people is incredibly inspiring and refreshing.
Practice the art of adaptability
Adaptability will be the hottest skill in town in 2025. And the best way to get comfortable with it (IMHO) is to practice adaptability by taking calculated risks.
To take calculated risks, that means:
- Creating your own projects, ideas, and self-directed challenges
- Celebrating small changes and incremental progress
- Digging into research, play, experimentation, strategy, and planning
- Identifying what negative self-talk is holding you back
- Challenging negative self-talk with self-compassion
- Opening yourself up to more and more feedback
- Preparing for contingencies with a Plan A to C
- Understanding what perfectionism costs you. And uncoupling from it
- Learning by doing
- Working on your coping skills and making self-care a priority
- Not making fun of other people’s mistakes so you’re kinder to your own
- Entering situations where you’re not assured of success and going for it anyway
- Learning to love words and phrases like I quit, no, I don’t know, and I failed
And above all else, don’t take your ideas or yourself too seriously.
Curious to find out more?