5 Tips for Taking a Leap (With Minimal Fear)

There have been a few times in my life when I’ve done something that prompted people around me to either call me nuts or sigh with jealousy and ask how I did it.

The first time was shortly after graduating from college, when I moved from Michigan to Washington, DC without a job – and within six months found myself in a job that ended up providing a gateway to a fulfilling career path. The second time was near the end of my 20’s, when I walked away from a successful career to live in France for a year without an income, attempting to write a draft of a novel. And most recently it was at the beginning of this year, when people learned I was leaving a company I adored to start my own business.

I’ve reflected on those experiences and tried to summarize the nuggets that other people seem to want to know when they ask how I did it. Here goes…

1. Make big leaps, not blind leaps. While each of these moves marked a pretty huge shift in my situation, none of them were spontaneous. Months of planning went into each one so I had done what I could (in advance!) to limit the risks.
2. Create a nest egg to live off. Part of that planning involved squirreling away money so I knew I could afford the leap. I’ve always made a point of not buying something I couldn’t afford, and part of every paycheck I’ve ever earned has gone toward both savings and retirement. When contemplating a radical change, I saved up not only for the adventure itself – but also for re-entry in the event that it didn’t work out.
3. Create a roadmap. While I didn’t know how it would turn out (and still don’t!), I headed into each of these situations with a goal for where I wanted to end up, and some mile markers to watch for along the way to ensure I was staying on the right path. It’s a lot easier to leave the traditional path if you have a destination in mind – and a narrative that will work regardless of how it all turns out.
4. Trust your safety net. Think about it – you probably have an incredible network of friends and family who have supported you and helped you arrive at this place in your life. These same people are going to do everything they can to help you succeed – or get back on your feet if you fail – in your new venture. The leap doesn’t seem as big when you know you have people to catch you.
5. Know your worst-case scenario. I tend to be a contingency planner by nature, so I can’t help but imagine all the various ways a plan can go wrong. Each time I made a leap, I’d think through the absolute worst outcome – and still decide it was worth it. In almost every case, the worst case is ending up broke, unemployed and facing potential debt. But here’s the thing: I know myself and I’d never let it get that far. I’d bail and find another job – even if I was overqualified to do it – to establish a cash flow if I needed to. And even if I DID have to bail, chances are I would’ve learned a ton in the process of failing, which would’ve made it all worth it.

Finally: we’re all a lot luckier than we realize. There are so many things that COULD go wrong each day and don’t. We don’t stay home from work because we MIGHT get hit by a bus or MIGHT catch the flu from a co-worker. So why do we let other “what-if” scenarios stand between us and our dreams?