What's the biggest risk you've ever taken? Did you fall flat or did you succeed wildly?

Each of us has a risk vs. reward threshold in careers and in life. For some people, asking for a raise or volunteering for additional responsibilities can seem like a risk. For others, like my friend Harriet, biking solo from Vancouver, Canada to the Mexican border was an acceptable risk for the adventure payoff. I fall somewhere in the middle. To many of my friends and colleagues, the decisions I've made--such as moving to Russia without speaking the language or knowing a soul, and my decision to leave a comfortable, stable, and well-paying position to start a company in an industry I knew nothing about (healthcare)--were huge risks. But I was able to evaluate and de-risk these decisions by applying a simple formula that I've used for my whole career.

To evaluate whether a risk is worth taking, it's important to examine your core: where and how this risk will stretch you, and whether you actually want to stretch in that direction. You'd better want it, because risks and stretch goals require resilience, passion and effort, and failure is always a possibility.

My risk evaluation formula uses a simple analogy: imagine you are a rock-climber, either on a rock-face in the beautiful wilderness or an indoor climbing gym. As a rock-climber you are always keenly aware of where your four limbs are: your footholds and handholds are what keeps you on the wall.

Assuming your ultimate goal is to climb up that wall, you can do that only by moving one limb at a time. Move two limbs, and you'll need to have super-human core-strength to stay attached to that wall. Move three and you will most likely fall off the wall and need to start over again. But when you have three limbs holding the wall, you have a strong foundation from which you can stretch one limb to a new location that gets you closer to the top.

When I moved to Russia to run a $400M business for Microsoft, I had three positions of strength: I understood the company, the products, and my role. The stretch was that I did not understand the specifics of the market (the Russian customer, culture and language). While this may seem like too many points of stretch, it wasn't. Knowing how the company worked and how to market and position the products were my strong foundation. I knew I could learn the culture and local market, and some of the language. Plus I figured that if it didn't work out, I'd have some good stories. It did work out: we managed to grow the business during an economic crisis and develop a market for legal software in a country that had 98% piracy. Plus, I made lifelong friends and have some excellent stories, but you'll have to buy me a vodka to hear those.

The same can be true for my decision to start a healthcare technology company. Between my cofounder Mike and I, we have the foundation to build and market great technology products. We both have prior startup experience. We actually met at a startup that Microsoft acquired in 2001 and we have worn many hats in the software world. What we didn't have was experience in the healthcare industry. (Similar to the situation with Russia, we didn't know the specifics of the market or the language.) We built the company on these strong foundations, and continue to stretch and take risks based on early success like awards from Mayo Clinic and HIMSS and successful clinical outcomes from a Boston University study.

If you're considering a move or a change of any kind and it seems risky, try to evaluate it using this rock-climber method:

1. List your points of foundation.

Do you have at least 3? Are they strong points?

2. Determine what you are reaching for.

Do you believe you have the strength and resilience to get there? Do you feel conviction about going in this direction?

3. Imagine what will happen if you fail or fall.

Is this something you can live with?

4. Reach for the new goal.

If you succeed, look for the next one. If you fall, get back on the wall.

Good luck, and let me know how it works for you.
Anne Weiler is CEO and co-founder of Wellpepper, a clinically-validated and award-winning platform for digital patient treatment plans. She cofounded Wellpepper in late 2012 with Mike Van Snellenberg to address issues in communication and continuity of care after a personal experience when her mother was released from 6 months in the hospital with no instructions and a month for a follow up visit. Anne's expertise spans concept to go-to-market for technology startups and established businesses. Prior to Wellpepper, Anne was Director of Product Management at Microsoft Corporation. She joined Microsoft in 2001 with the acquisition of Canadian web content management company Ncompass Labs.