In April 2008, our family was expecting our second child. The mortgage crisis was about to blow up the global economy and my wife was nine months away from having her job and our health care benefits disappear. That was when I chose to take the biggest risk—and ultimately the best decision—of my career.

I had a pretty good resume at that point, but I had decided I was ready to set out on my own. I convinced my wife it was a good idea to take out a home equity loan so I could launch a website on airport parking, of all things.

By the time we had invested more than $150,000 of our own money into the site, our son was born, but we’d also lost my wives’ steady income and health benefits and the economy was in the toilet. Luckily, the business had taken off.

Whether you’re playing blackjack or making life decisions, taking calculated risks is a huge part of being successful. Business lore is littered with exciting tales of entrepreneurs putting it all on the line, but the most overlooked piece is what happens before that. Without the proper preparation, they generally don’t make it.

Regardless of the path you end up choosing, I suggest three steps to put yourself in a position to take advantage of opportunities when they come along.

1. Focus on building skills early in your career.

Every financial professional preaches the power of compound interest. The earlier you start saving, the more time you have to accumulate wealth. The same thing applies to building skills in your career.

For me, that meant working with smart people at interesting companies where I could learn. There were multiple times that I gave up a little money or a title to put myself in a situation where I thought I could learn more.

By the time I was thinking about starting my own business, I had a strong base of skills underneath me. That allowed me both to assess my risk and execute my vision.

2. Be cautious with your spending.

How would you feel doing a trapeze act for the first time without a safety net? It’s exactly the same with your personal finances and career moves. Almost all great opportunities will involve some financial risk, so it makes a big difference if you’ve built even a small financial safety net.

The best way to do this is to manage your expenses. When I bought my first brand new car, I didn’t buy the most expensive car I could afford. Instead, I bought one with hand-cranked windows, no radio or speakers, no air conditioning and a manual transmission. It ultimately helped provide a little bit of cushion to take monetary risks elsewhere.

3. It’s okay to be afraid to make a leap—just do it anyway.

There’s a rope swing on the side of a lake at our favorite vacation spot. You have to clamor up some precarious rocks, step out onto slippery tree roots and then brace yourself to jump.

Once you get up there and look down, it’s kind of scary. But when you leap out, it feels great: the air rushes at you as you pick up speed, there is a moment of weightlessness when you let go and then the sound changes as you plunge into the brisk water.

It’s the same thing when you’re starting a business or taking a career risk. It wouldn’t be a risk if you weren’t afraid. But once you’ve done it, you look back and wonder why it took you so long to jump!

Erik Budde is CEO of RothIRA.com and TraditionalIRA.com. These sites offer plain and clear explanations of important retirement planning tools, helping consumers plan for their future and invest in the most tax efficient manner possible.