How to Be Successful at Taking Risks

Getting ahead usually means putting something on the line, and that part rarely feels good. Fear around risk is ordinary. What changes the odds is the approach you bring to it. Pick your risks with some thought behind them, and the chance of a payoff goes up, whether the area you're working on is your career or the people close to you. The fear doesn't vanish, but it shrinks enough that you can actually move.

Start by giving yourself permission to dislike this. Most of us resist change because it drags us out of the familiar, and being nervous about that is simply how people are wired. There's some relief in realizing your reluctance isn't a personal flaw; plenty of others feel exactly the same. Just don't let that reassurance turn into an excuse to stay put. The point is to learn how to take risks and watch good things follow from them.

A risk is whatever makes you uneasy, and that definition is broader than people assume. Say the word and minds jump to the dramatic version: walking away from a paycheck with nothing lined up, or jumping out of a plane. In practice, a risk is anything that pushes past what feels safe to you. If you never wear dresses, putting one on for work tomorrow counts, because it sits outside your comfort zone. Spend a minute listing a few small ones you could try soon, just to get moving.

Begin tiny. Marching into the office to hand in two weeks' notice with no plan is not where a beginner should be. Dip a toe in first. Wear red lipstick. Shave off the beard. Skip the gym and go run at the park instead. Each of these is unfamiliar enough to register as a risk, and once you feel how freeing it is to do something off-script, the bigger decisions start to look less impossible.

Your imagination will fight you, so turn it down. Imagination is useful most of the time, but it also feeds a fear of the unknown, and the unknown holds plenty of good outcomes too. When you're weighing a risk, the mind drifts straight to everything that could go wrong. Push back on that. Quiet the catastrophizing and make yourself picture the upside instead. Leaving a job isn't a one-way ticket to unemployment; it can be the move that lands you work you actually like.

Big risks deserve a plan and a safety net. Spontaneity has its place, but a major life decision is better with a few protective measures built in so the gamble has room to work out. If the risk is finding a new job, hold onto the current one until the next is locked down. That old paycheck is the cushion in case the dream role falls apart, and it keeps you going until you're ready to bet on the next opening.

Work one risk at a time. If both your career and a relationship need a leap, choose which one to tackle first rather than juggling both. Stacking risks gets overwhelming fast, and that pressure tends to push people into bad calls. The real skill in using risk to get ahead is knowing which ones to take, how to go about them, and when the moment is right. Keep your attention on a single risk and you can actually plan all of that out, which is where the larger rewards start to become possible.

Rosemary Kitchen. Source: Motivation for Dreamers (2015), "Risk Taking: Take a Risk," retrieved March 19, 2015.