I was terrified, but I was comfortable.

That was the way it felt almost 30 years ago when I started my first company. I was gainfully employed, making an extraordinary salary, had all the perks and privileges of an executive position in a thriving company at the age of 27, and yet I knew it was not the place I was meant to be. But I was terrified by the prospect of the uncertainty in breaking out and following my passion and my dreams. I knew what I wanted to do, I just didn't know how it would work. I could make the business plan show anything I wanted it to show, but that didn't make it real.

A battle was raging between my heart and my head; passion against logic, and logic was winning.

"I also realized that while I might forgive myself for ignoring logic, I'd never forgive myself for ignoring my heart."

Security made sense. The economy was in a horrid recession. Every ounce of my intellect told me I should stay put, stay exactly where I was, be safe. Most of my closest friends thought I was nuts to consider building my own business when I had so much going for me. There was too much risk, too many unknowns, I didn't have a track record as an entrepreneur; all that and dozens of other really good reasons.

But it wasn't about logic, it was about making a decision that I knew I needed to make and one that I'd never let myself off the hook for not having made.

I realized the risks, but I also realized that while I might forgive myself for ignoring logic, I'd never forgive myself for ignoring my heart.

All of the agony ended when I finally stepped into my boss's office one late summer's day and handed in my resignation. He was shocked and asked me where I was going. I made up a story about having investors backing me on a new venture. I couldn't take one more person telling me how foolish it was to strike out on my own in the midst of one of the deepest recessions in decades when I had a virtual guarantee of security where I was

"...it wasn't about logic, it was about making a decision that I knew I needed to make and one that I'd never let myself off the hook for not having made. "

Amazingly, the minute I stepped out of his office all of the terror, fear, trepidation, ambivalence, and doubt just disappeared. It all ended in the instant I decided to take that first step. I often tell people agonizing over starting a business, or life's exceptionally tough decisions, that making the decision is the source of 99% of their agony, not what lies on the other side of the decision. Once you commit yourself to a path it's absolutely crystal clear what you need to do, you figure out how to do it, and then you just do it. Just make sure it's what you really need to do!

That's where it get tough. The simple truth is that life's really important choices are rarely black-and-white. Most often they span infinite shades of gray. But when indecision creeps in, when the path forward is shrouded in fog, only one question really matters. What will you truly regret not having done.

In my experience the path to figuring that out is not that hard. You can chart it out by asking yourself these five questions whenever you're making a life-changing decision like starting your own business:

  1. Do you want to do this or do you need to do this? The Difference between want and need is an important one. What we need is deeply rooted in our values, ambitions, goals, and beliefs. What we want is imposed by context, social constructs, and peer influence. Be sure you are making the decision based on need.
  1. Will you truly carry the regret of not having done this? Only you know what you will ultimately hold yourself accountable for. First be honest about your needs and then make a decision to either pursue them with no holds barred or be able to live with having let them go.
  1. Are you being held hostage by the fear of the decision rather than the goal? We often wrap ourselves around the axle of the decision as though it were the goal. The decision is just the gateway to the goal. There are some things that you can spend a lifetime analyzing and weighing and still not come to a decision based on the facts, because the facts lie on the other side of the decision, not in the past. Get over the fear of making the decision and it's amazing how clear the future becomes.
  1. Have you thought through the worst and best possible scenarios on each side of your decision? This is a tough one because the truth is that you will never really know what the best or worst outcomes are until you experience them. But go through the exercise and figure out what the most likely best and worst outcomes are. Then Decide if what you want to do is maximize the upside or minimize the downside. If what you really want to do is minimize the downside and play it safe chances are you'll never decide. Great, you just made a decision by default.
  1. Is it YOUR decision? Lastly, be sure that the decision is one that YOU want to make. You'll never be at a loss to find well-meaning colleagues, friends, and relatives who are generous with their advice about what you should do. But it's your business, your life. All too often we end up making decisions to please others. While advice is abundant you're the only one who has to live with and is accountable for your decisions.

If you answered that you NEED to do this, that you'll carry the REGRET of not having done it, that you don't want to be held HOSTAGE by fear and the past, that you want to maximize UPSIDE, that you are making YOUR decision, then congratulations, your decision is clear.

Now all you have to do is actually make it!