Why Feeling Comfortable Is a Bad Sign

If you’re happy where you are in business, that’s a clear sign it’s time to reinvent.

Comfort is our worst enemy. Though I’ve long suspected this to be true, a recent conversation with an entrepreneur I know in Fort Worth, Texas, brought it all home for me.

As the founder of The Starr Conspiracy, Bret Starr has spearheaded a first-of-its-kind strategic marketing and advertising agency that has grown remarkably since its inception in 1999. Starr grew up without the comfort of financial security, and he says one of the biggest benefits of starting out that way is being emotionally comfortable when you’re financially uncomfortable.

As a person in charge of a brokerage, you may feel you have a lot to lose, but Starr says it’s only when we make decisions from a place of having nothing to lose that we’re free to be creative, take risks, and reinvent. That lesson is true on an individual level and on a business level; being willing to be uncomfortable puts us in position to thrive.

However, this isn’t about being reckless. In fact, it’s quite the opposite. Brokers who can become comfortable with discomfort are able to operate on a totally different plane by eliminating dependencies and rebuilding a sustainable model.

To Starr, eliminating dependencies is one key to positioning yourself for growth. That means that the very agent you think you can’t live without is the one you must learn to live without. Often, the “hero” on your team is high maintenance and lowers the morale of the team. When you put yourself in position to be dependent on one top producer, you lose your freedom. Parting ways with anyone who lowers the morale of the team is a good long-term investment.

Eliminating dependencies allows you to build a sustainable model of shared risk across multiple valuable team members. Starr recently came to this point in his own business. He told me in an interview that he thought to himself at the time, “If we don’t change something big, we are going to work ourselves to death and have nothing to show for it.”

They decided to transition to what’s called a flat organization — one that requires little management, where the team collectively decides how work gets done. This is not a common approach in advertising agencies and no one knew if it would work. Making a drastic change with a successful business is risky and Starr did it at a time when they all had a lot to lose. He and his team knew it would either destroy them or position them for greater growth over the next 10 years. Though they had some touch-and-go moments, it all worked out in the end.

Reinvention is necessary in any life, on both a personal and organizational level. Starr advises that if you ever look around and think you are as far as you can go in the situation you’re in, it’s time to get up and look further. If you’re serious about being an entrepreneur, you’ll should also expect this attitude from the major influencers in your life. Keep company with people who pull for you and pull you up to that higher plane. If you’re not surrounded by people with the attitudes, behaviors, and beliefs of successful people, remove yourself from the situation.

Conflict is uncomfortable. But oftentimes challenges and conflicts are exactly what we need because they force us to dig deeper and find something better than the status quo. That’s where we find that sweet spot that allows us to do and believe and achieve what doesn’t seem possible. It’s where underdogs triumph and deep-seated traditions and beliefs change. It’s where life happens.

The only way to thrive is to operate without fear. The disruptions and discomforts in our lives can catalyze a complete transportation. It’s scary as hell. But it’s also where the magic happens.