“When things go wrong, it makes my mind wander to why I am doing this. Am I really cut out for this? Am I happy? Is this what I want? We tend to forget why we started on this journey in the first place.” 

For us entrepreneurs, it is crucial that we find time to evaluate our lives. Being an entrepreneur can be a stressful and all-encompassing endeavor. Many entrepreneurs have started their venture only to look back and say, “Where did my life go?”

The Wrong Time to Evaluate

There must be time (often with a glass or two of bourbon) for you to reflect, think about the big picture and evaluate your personal goals. Not having this time to reflect can be damaging. The problem is, entrepreneurs often feel compelled to investigate their personal life only when the shit hits the fan—at the busiest, most inopportune moments in the middle of the business day. This is precisely the time not to do it.

When entrepreneurs feel overwhelmed, the gears come to a stop. Running in quicksand becomes walking in quicksand, and then sinking in quicksand. When this happens, for some reason it causes many of us to use this as an opportunity to evaluate our lives. Maybe because we’ve come to a grinding halt, we think it’s time to ask:

What am I doing? I have no life. I never sleep. I don’t talk about anything but this business. Everyone thinks I am crazy. I never go out. I haven’t been on a date in months, my wife/husband/children are going to forget my name soon, I’ve forgotten what the outside of my office looks like. My friends have given up on me.

Meanwhile, work piles up like a multiple vehicle car crash and your employees or your cat (if you’re working solo) begin to wonder what’s going on.

If we gave every entrepreneur truth serum and asked them how often this occurs, the answer would likely be: “at least once a week.” Regardless of how often it occurs, it most often occurs “right after getting punched in the face for ten rounds.” It almost never occurs when things are going well. Have you ever evaluated your life after you close a deal? I doubt it.

The Negative Implications

If you choose to evaluate your life during the most challenging times or in the middle of your day, it can become debilitating.

• Wasted Time and Energy. First – it consumes significant time and energy. When thoughts about the meaning of life arise, they distract us from the tasks at hand—the tasks that advance the business and make the issues of the day improve. More importantly, it consumes energy that would otherwise be used moving the business forward. These thoughts are not easy ones and they tend to bring up a variety of sensitive subjects and emotions. These feelings easily overwhelm and it’s impossible to stay present and attend to your business, while simultaneously evaluating the meaning of life.
• Bad Decisions. Second – these thoughts are often reactive and emotional and result in bad decisions. When the pressure hits you, it is hard to be objective. The grass seems greener, well, everywhere else. If you are venting, it can be harm- less. If you are making decisions and acting, it is a problem. You can’t evaluate whether to fight, and how to fight the fight, when you are still in the middle of the fight.

The Right Time to Evaluate

While you shouldn’t evaluate the meaning of your life every day, you must put aside time to do it on a regular basis. Otherwise, you fall victim to the momentum of daily activities and obligations without asking yourself, “Am I happy?” For years, I didn’t do this.

But not asking yourself periodically whether you are happy can lead you down a path of doing what you do today because you did it yesterday. There are always changes you can make. Bring in more capital to enhance your team. Change your role. Sell your stake in the company. You always have choices.

Set aside a time for two hours every other weekend either alone, or with someone you trust who is not involved in the business. You want to reflect when no one is watching. This is a time not to be on stage and to be candid with yourself about where you are.

During this time, ask yourself the following questions:

• Happiness. Am I happy? Even with the challenges, am I enjoying the journey? Do I get fulfillment about the progress we are making? Do I get excited when we win a customer, hire an employee or finish a project?
• Sacrifice. Is the pressure and strain worth the sacrifice I am making? Be candid with yourself about the sacrifices you are making. They may be personal or financial or the opportunity costs of not doing other things. There is nothing wrong with sacrifice, as long as that sacrifice feels worth it to you.
• Doing Things You Like. How can I remove myself from the parts of the business I am not good at or I don’t like? Understanding the parts of the business you are not good at or that you don’t like are important to growing your business. This is also important for you. These are the elements of your day that are draining you. Identify these parts and use this time to think about how to remove them from your day now or in the future.
• Do I Want to be CEO? Do I want to be the builder or the visionary? Do I want to be CEO? I know your first reaction: “How dare you ask me this question? After all that I have done to get here, now you don’t want me to be CEO?” At first, this is an uncomfortable question. Of course, you want to be CEO—you built it. However, being the CEO of an early stage venture is more about building the foundation of a business and managing its daily operations, than it is about your vision. The CEO must do all of the following and more:
  • Set the priorities of the company
  • Align the organization to those priorities
  • Ensure that the company is properly funded
  • Inspire people to stick to the vision
  • Clearly communicate to the various constituents of the business.

Ask yourself, “Given the parts that you enjoy, and the ones you don’t, and the parts that you are good at, and the ones you are not, is there a role that would be fulfilling but different from being the CEO?” Once you get over the shock of the question, you might realize there is a role for you that isn’t the CEO, but that is more fulfilling. It might allow you to get back to your vision, help the company, and remove you from the pressures of a job—CEO—that you are not sure you want.

This is a subtle perspective shift but one that can have a real impact. Taking the time to check in with yourself is critical. But you can’t fight the fight and evaluate your life at the same time. Set a time for yourself every two weeks to check in and take stock of yourself. When the thought creeps into your head in the middle of the day, resist the temptation to address it and wait until your designated time. Put it on your calendar and never miss it.