Entrepreneurship Is a Mental Game

I was asked to give my input on a program being developed to help diverse Atlanta entrepreneurs. I’m excited about the program and can’t wait for it to launch. The creators asked me a tough question: “What mental challenges do founders face?” The fact that they’re thinking about this and wanting to help founders address these challenges is encouraging.

Here are a few things I shared:

  • Release – Founders should understand the one thing they enjoy and need outside of work to be the best version of themselves. It could be exercising, playing video games, attending sporting events or live concerts, or anything else. Whatever your thing is, make it a priority so you’ll have a mental release.
  • Imposter syndrome – Founders are constantly in environments and situations where they feel they’re unqualified and unprepared to handle whatever’s going on. They often fear failing or being exposed to others as a fraud. This is normal and usually unfounded. Most people know entrepreneurs have gaps but still root them on. Not because they’re perfect or have all the answers, but because they have the courage to try to do something great.
  • Benchmarking – Founders will sometimes compare themselves to their peers. This is a mental trap. Everyone’s circumstances are different. Timing also plays a huge role in success. Just because someone else is succeeding and you aren’t doesn’t mean you won’t ever. Be happy for them and know your time will come.

There are lots of other mental challenges, but these are a few that I think many founders have had to overcome. Entrepreneurship is a mental game. Going into the game knowing what to expect can . . . well, be a game changer. Entrepreneurs will be able to be more proactive than reactive during their journey. I’m excited to hear that diverse founders will get help with the mental side of entrepreneurship!


Weekly Reflection: Week Forty-Three

Today marks the end of my forty-third week of working from home (mostly). Here are my takeaways from week forty-three:

  • Optimistic – I’m not sure how 2021 will play out, but I’m optimistic. I’m hopeful that we’ll begin to trend in a positive direction. I know the country’s problems won’t be resolved overnight, but it appears we’re pointing the right way.
  • Work from home – I may soon return to working exclusively from home. I’m not excited about this, but it may be the prudent decision.
  • Year of change – I’ve had a few conversations with people close to me who are considering making big changes in their lives. This year, 2021, may be a year of change for a lot of people.
  • Groove – It’s been hard for me to settle into a good working rhythm since the holidays. I’m hopeful that next week I’ll have my groove back.

Week forty-three was a short week because of the Monday holiday but otherwise pretty normal (well, what passes for normal these days).


Journeys Don’t End, They Cycle Around

Today I met with a successful entrepreneur who recently sold his company. He shared his views on the entrepreneurial journey, which he sees as an evolution. I totally agree. My attention was caught by his term for one stage of the journey: “rebirth.” After you have the idea, build the company, exit the company, and overcome the post-exit phase (i.e., separate yourself and your identity from the company), there’s another phase. He views it as the beginning of a new chapter, which will be different for every person. It’s the “Now what?” phase.

I’ve never heard it articulated this way, but I agree with him. When you’re focused on something for a long period of time and then it’s gone from your life, there’s a time of transition. A time when you think, “Now what?” I think rebirth is a natural part of everyone’s (not just entrepreneurs’) evolving life. Parents whose children have left home. Anyone recently retired. Someone recently laid off. People who are widowed or divorced.

Rebirth can be uncomfortable, even deeply painful depending on the circumstances, but it’s also an opportunity. A chance to steer your efforts in a new direction and grow in a different way.  A renewed existence of sorts. A do-over. Whatever journey you’re on, it won’t end; it will just cycle around.



Time is often called the great equalizer. You can’t buy, sell it, or trade it. Everyone gets the same 24 hours a day. The only thing you can do with time is manage it. As a youth, I was often reminded of this by elders, but it didn’t resonate with me. It wasn’t until I was a founder that I learned how managing time effectively can change your trajectory.

When I was asked recently for my views on this topic, I shared a few habits and tricks I’ve adopted over the years. Here they are:

  • Mortality – I use this Chrome extension to remind me how much time I have left to live. It’s a (yes, somewhat morbid) subtle daily reminder to not waste time.
  • Weekly reflection – I reflect on the past week in blog posts, numbering these weekly posts so I can keep track of the weeks. I started doing this early in the pandemic to track how many weeks I’d been working from home, and it morphed into a broader reflection. Here’s a recent post.
  • Schedule – I try to think about what types of activities I want to work on each workday. I’ve blocked out time for certain things and I use this technique as a guideline and reminder about what I should be focusing on.
  • No – I say not to a lot of things to protect my time.
  • Time vs. money – When I have the option of paying (a reasonable amount) for something that saves me time, I normally decide to pay. I figure I’m going to pay in time or in money. I can make more money, but not more time. I understand that I’m fortunate to be able to make this choice and that not everyone is. I appreciate my good fortune and don’t take it for granted.

These are some things I’ve learned and adopted over the years. I understand that they won’t work for everyone, and I’d love to hear how others manage their precious time.  


Learn by Extending a Helping Hand

I’ve been listening to a friend talk about a deal he was considering. It was a big real estate deal, something I’m not experienced in. I didn’t have a stake in it, but I decided to help in a way that leveraged my strengths. I’m a numbers guy, so I built a crude financial model to help clarify the worst-case scenario. We talked it over and he shared his insights on what the model was saying and things it didn’t account for.

Today, I learned that the deal fell apart. Not the outcome we were hoping for, but I realized that supporting my friend had been a great experience. First, it always feels good to contribute to someone else’s success. My assistance wasn’t material (in my opinion), but every little bit helps when you’re trying to do the impossible. Second, helping my friend, who’s experienced in a space that I consider a future area of interest, was a terrific opportunity for me. I learned a lot, fast, from the combination of his wisdom and my own research.

If you’d like to learn about an area or gain some experience in it, try to find a way to offer your skills, free of charge, to someone knowledgeable. Give back by helping a friend or colleague . . . learn about something that interests you . . . it’s a win–win!


Done Is Better Than Perfect

I’ve been working on a project for a few weeks. My vision was to use the most advanced tech to make it a success. I wrote down what I was trying to accomplish and began researching. Ideas for solutions came from others along the way. But my vision slowly deflated. To my surprise, my dream technology doesn’t exist. When I talked to people who live the problems I was working on, I learned they’re using manual workarounds or legacy tech. The more I dug, the more frustrated I felt.

I was forced to accept that the perfect solution I envisioned isn’t possible. So, taking a step back, I reviewed my goals for this project. This reset my perspective. I was reminded that I was looking for the solution that best checks certain boxes—it doesn’t have to be perfect. In the end, a legacy technology was the best option. It’s not slick (in fact, it’s clunky) or cutting edge. But it efficiently does what I need done. I embraced it and wrapped up that part of the project.

I was reminded of a common start-up mantra: done is better than perfect. Sometimes the best solution isn’t glamorous. It just works.


Great Questions Can Lead to Great Outcomes

Decision-making and quick learning are keys to success. If you can learn quickly and apply your new knowledge to improve your decision-making, you’re more likely to achieve your goals. As I thought more about how I’ve observed others learn, another pattern emerged: great questions.

Whenever I meet with successful people, they ask me great questions. I often leave meetings thinking about things that had never before occurred to me. They usually don’t tell me what to do, but nevertheless they have a huge impact on my decision-making.

Great questions don’t always have to come from other people. In difficult situations, I’ve had some tough conversations with myself. I’m capable of asking myself tough questions! Where am I failing? Why am I doing this? What’s my biggest fear for this project? Answering such questions honestly has clarified things and helped me make better decisions and push through.

Great questions can lead to great outcomes. If there’s something great you want to accomplish, consider putting yourself in position to be asked great questions.  


It’s OK to Change Your Mind as You Learn

Decision-making is one of the main responsibilities of leaders (all leaders, not just entrepreneurs). When you lead a team, others look to you for guidance. Making decisions that affect only you is one thing. Knowing that you’re affecting other people’s lives is quite another—and it makes decision-making more difficult.

I’ve had the good fortune to spend time with great entrepreneurs, and I’m always curious about how they approach decision-making. From what I’ve seen, everyone’s style is different and there’s no wrong way to go about it. However, I’ve noticed one pattern: they’re not afraid to change their mind. I didn’t know what to make of this at first. Was it indecisiveness? Lack of focus? Eventually, I figured it out: none of the above. They were learning. They allowed their thinking to evolve based on new information. They were unafraid to admit they’d been wrong and change their mind.

Some people struggle with making decisions that affect other people. And rightly so. There have been times I’ve worried about making the wrong decision, and I still struggle with it from time to time. Over the years, though, making decisions has become easier. I remind myself that they usually aren’t set in stone, and it’s OK for me to change my mind. It’s even OK to admit that I was wrong!

The next time you have to make a decision that affects others, make the best decision you can with the information available to you. That’s all anyone can expect of you. And remember: it’s OK to change your mind as you learn.


Weekly Reflection: Week Forty-Two

Today marks the end of my forty-second week of working from home (mostly). Here are my takeaways from week forty-two:

  • Schedule – I thought about my schedule in 2020. There were some things I liked about my schedule but others I didn’t. I’ve adjusted it a bit and am blocking off bigger chunks of time. I’ll see how this works and finalize something at the end of the month.
  • Community – I’ve been thinking about community and talking to people about it more. It’s top of mind for people personally and professionally. It’s a real problem—that is, lack of community in this pandemic age is a problem—that people are actively trying to solve in a safe way.  
  • Founders – I enjoyed my conversations with founders this week. Their energy and passion was refreshing.

Week forty-two was a steady week. Looking forward to celebrating (virtually) the MLK holiday on Monday.  


Timing: A Big Factor In Success

Today I spoke separately with an investor and a founder who both mentioned how timing beyond their control had an big impact on them.

The investor has been at it for many years. When he started raising his first fund, it was tough because his thesis didn’t resonate with many people. Today that same thesis is popular and has allowed him to raise his latest fund quickly.

The founder has been solving a painful problem for years. When he began, his target customers weren’t open to a digital solution (yes, industries like this still exist). The pandemic has forced them to adapt, and they’re readily using his digital solution.

These two people haven’t changed what they’re doing. They’ve stuck to the same script. The difference is that the timing is right—the market now values what they’re doing.

Make no mistake. Timing is a big factor in success. It may not determine success, but it heavily influences it. Unfortunately, people are usually at its mercy. Everything can be right except the timing, and there’s not much you can do about it. We can’t control timing, but we can be aware of it and act accordingly. I’ve seen founders know they were on to something big but also aware enough to know the timing wasn’t right. Some of them chose to spend their time and energy on something else. Others worked on perfecting their solution until the timing was right. I’ve seen both approaches lead to success. The key was awareness, which allowed them to make proactive decisions that factored in timing.

The next time you’re trying to do something, ask yourself, “Is the timing right?”


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