How I Found True Success: The Big Realizations of a Satisfied Entrepreneur

A rich man with no money is still a rich man, but a poor man with a lot of money is still poor. What do personal goals have to do with your business? According to one entrepreneur -- everything.
July 16, 2015

One of the biggest realizations I have had as an entrepreneur is that I am more successful when my personal and business goals are both aligned and directly reflected in my business. My co-founders and I carefully invested a lot of energy into crystallizing our personal and professional goals before we even began to lay out the ideas that created our current venture, IMM, a digital advertising agency.

We talked about our life goals, business philosophies, work styles and what attitudes we wanted to bring to the office every day to be successful. We shared dreams about how financial freedom would impact our lives for the better—including our future individual net worth goals. We even wrote aspirational dividend “checks" to ourselves to be “cashed" at a future date. By working backwards from our desired experience and outcome, we made sure that our business delivered daily fulfillment. You'll be more successful in the long run if your business is set up to serve you.

These five key insights helped me measure success not only in terms of the enterprise value generated, but also in the happiness created along the way.

1. Hit pause on your ideas and develop a deep understanding of why you are starting a business.

Is starting a business the culmination of a lifelong dream? Are you frustrated by the ups and downs of working for someone else? Did you suddenly wake up and realize you've been living someone else's life? How much money do you want to make and over what period of time?

It's crucial to have a healthy relationship with money, and understanding this can have a tremendous impact on what you do for a living. I have colleagues who have decided they don't need a lot of money to be successful and happy. They save a lot, live well beneath their means and seek fulfillment in things that don't require much money. They tend to be the ones we would consider “lifestyle" entrepreneurs, those who are less focused on generating large scale wealth, and therefore structure their businesses so they can, for example, live in a vacation destination or dedicate some time each day to a leisure activity, like surfing.

On the flip side, I also know millionaire investment bankers who work 80 hours a week, yet live paycheck-to-paycheck to fund their aspirational jet-set lifestyle. Although your goals and values will continuously evolve, it's hard to measure success unless it's been well defined. Understand your goals prior to identifying a business idea and then look for ideas that will help you achieve them.

2. Have an honest conversation with yourself about what your day-to-day work experience will be.

Can vision alone sustain and inspire you during the leaner early stages? Do you like working long hours? Are you energized by working with customers? Office politics? Managing others? Travel? You may be surprised by the answers. Some of the happiest and most successful people I know have found true wealth by embracing their honest answers to these questions and fearlessly building a business or career suited to who they truly are versus who they think they are supposed to be.

A senior colleague aspired to lead a venture-funded technology company. She was on the verge of accepting the CEO role at an adolescent firm with a bright future. This company needed a field general, a strong manager who would be heavily involved in the day-to-day. When this experienced professional took the time to visualize the details of what her typical day would be like, she realized she was more fulfilled by strategy than management.

Crucially, she also realized that she had been telling herself that she had to be a CEO. She refocused her priorities and today is a very happy and fulfilled strategy consultant—with zero direct reports.

Sometimes what we tell ourselves isn't what plays best to our strengths. Be honest with yourself and you'll avoid situations that may look like success on the surface but can ultimately lead to unhappiness.

3. Don't be driven by fear of loss.

My grandfather once said, "A rich man with no money is still a rich man, but a poor man with a lot of money is still a poor man." If you continually inhabit a place of scarcity, nothing will ever be enough. You may find that you are making money, or driving your team, out of fear of being personally poor—and either way, you will never have true wealth. You'll either be perpetually unfulfilled or you will squeeze the success out of your business.

I have also watched a number of companies lose clients because they were overly focused on not losing the business, instead of fearlessly doing what was needed every day, such as telling their clients what they needed to hear as opposed to what they wanted to hear.

A number of years ago we were required to re-pitch against several much larger companies in order to keep a client. The loss of their business would have had a significant impact on our young company. I asked my client if they were open to us retaining the business. The answer was yes. I asked my team if they still had heart for the client's business. The answer was also yes.

With that in mind, I quickly drafted strategic, staffing and financial plans that accounted for the loss of the client's business. I made my peace with the worst possible outcome – the loss of our largest client. Then I went back to my team and told them that we wanted to win, and to go all in—as if they had nothing to lose. We were instantly more relaxed, more creative and ultimately more successful. In the end we won, but I feel as though the real victory was the freedom we derived from letting go.

4. Remember that 90 percent of business success is determined by execution, not the initial idea, and that execution is a team sport.

Your business idea will evolve—if not fundamentally change—over time. People are your most valuable asset. They make those good ideas great, not the other way around. So make happy people your primary product. Recruit, train, inspire and empower the absolute best team you can attract. Invest in your people and they will reward you with a scalable, self-replicating meritocracy.

5. Practice your award acceptance speech.

Before you can be successful, you must feel successful. To feel successful, you have to dream about it, visualize it and celebrate all the little wins along the way. Allow the feeling of future success to become just as sustaining for you as your startup vision is for your team, clients and investors.

Photo: Shutterstock