How To Succeed By Taking Risks

February 23, 2019

This week I was having lunch at a local restaurant when I met a gentleman who was sitting next to me while having drinks. He was a tall, professional looking gentleman wearing a Peter Millar golf shirt and an Apple iWatch which has quickly become America’s understated symbol of affluence.

From his appearance I could tell he was accomplished. We soon began chatting and I learned that he was recently laid off from a large real estate company. He drank longneck bottles of Bud as he pondered his next move. He was standing at the crossroads of either finding a new job or taking the leap to set up his own shop.

It was apparent from our discussion he was full of trepidation about his upcoming decision. As an entrepreneur now on my second company (, we discussed why there was really only one decision that he could make and that was to set up his own shop, but he still had his reservations.

Taking a risk is inherently never an easy. Self-preservation and avoiding danger are genetically coded into our DNA. Not to mention the fact people try to avoid change at all costs. There are very few individuals who have succeeded greatly in life without taking some form of risk.

From explorers to industrialists, history books are packed full of stories of their exploits and successes. The United States was built by people willing to risk absolutely everything to create what is arguably the greatest nation the world has ever seen. A place where an individual’s success is measured largely by their efforts and how great a risk they are willing to take to achieve their dreams.

As we continued to talk I shared stories of my own experiences about the risks I have taken and joys of going it alone. In the majority of cases I’ve seen people take risks when their current situation has become unsatisfactory or intolerable. Taking the risk to start a new venture is often prompted not by the desire to enrich oneself but to do something more fulfilling and meaningful.

I could clearly tell that the gentlemen was conflicted by the differing advice he was receiving from his trusted advisors and family, each one with sound reasons both pro and con. The reality is the conditions For taking risks will never be perfect and a clear sign from the heavens will never come.

There is one sign that I have found that will help you realize whether you are on the right track or not. Whenever you are nearing a decision on starting out on your own inevitably opportunities will crop up that appear to be the safer and smoother route. These “opportunities” should be recognized for what they are, distractions that will keep you from your goal and achieving your true potential.

For me my “distraction” came in 2006 just when I was starting out on my own. I had been referred to an ad agency in California (which is one of my favorite states) that was looking for someone to run a major car account they had just won. Not only did they want to hire me, but they also offered to help my wife land a job at a major pharmaceutical company. I would have made significantly more than I would have hoped to make in the first few years of my start up. It was also one of if not the hottest ad shops in the country. After discussing it with my wife and a lot of soul searching I declined the offer and ran my own company for the next 13 years.

By no means am I suggesting that taking risks in business or life should be entered into lightly. The very reason you are even contemplating taking the risk is because you have honed your craft to a point where you believe enough in yourself and your abilities to provide real value to your clients and customers.

“If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.” -Henry David Thoreau

Taking calculated risks means doing the necessary research and obtaining the buy-in from all key stakeholders to help ensure success. This effort starts at home. If you are anything like me the risks you take not only affect you but can also have a profound effect on others. It’s important to get everyone on board because chances are their risk tolerances are far lower than yours. If they aren’t brought in from the beginning it can cause strife. Strife is the last thing you need when you’re pounding it out trying to run and grow your business. Home should be your sanctuary and your support structure will be just as important if not more so than your customers.

Throughout the ups and downs my family has stood by me because they bought into the mission and who wants a dull life anyway?

Nothing good is also ever easy, but if you believe in yourself and take the time to fully understand the risk you are taking in actuality you really have very little to fear.

I have often found that running your own venture is actually safer than working for others. This is evidenced by the downsizing experience of the gentleman who sat next to me at lunch. In your own venture you can at least see the punches coming. You might still get hit, but you have the ability to duck or protect yourself from the blow better than if you were working for someone else. The gentleman in the restaurant had run an incredibly profitable division for years and walked in one day to a pink slip.

When done authentically risk taking can become like an addictive drug each time getting a little easier to take. The freedom of being able to chart your own path and help clients the way you want without silos or the burdens of office politics can be exhilarating. Risk taking is not without its challenges but I will guarantee one day you will look back and wonder what took you so long to take the risk in the first place.

Here are a few tips I’ve learned along the way:

1. Secure The Home Front — Take the time to discuss your plans with your spouse and family so that they understand exactly what your are embarking on. Keep the lines of communications wide open so that they can come to you with questions/concerns. If possible give them a role in the new venture.

2. Build The Team — Assemble the very best team you can to help advise you along the way. The 3 most important advisors you’ll need will be your accountant, lawyer and banker. Sure you can set up LLCs and bank accounts online, but when the proverbial crap hits the fan you’re going to need someone to talk to for help.

3. Rainy Day Fund — Most new ventures take a minute before they start generating real and profitable revenue. Your bills won’t stop. As a part of your calculated risk taking equation make sure you build up a war chest and trim expenses where you can. If your venture is sound and your faith strong the money will come.

4. Level Your Horizon — It is critically important that you remain level and even keeled. There will certainly be periods of extreme highs and lows throughout the entire process. The secret is to remain grounded and view each challenge as an opportunity to grow and learn from. You can overcome anything as long as you don’t give up and keep working towards your goals.

5. Have Fun — Life is too short not to!

And remember… “Winners never quit and quitters never win.”

Good luck!