Early in my journey building CCAW, I kept a notebook. I wrote everything down. It was a catchall of sorts for whatever was on my mind. Projects I was considering. Daily priorities. Problems I was trying to solve. Meeting notes. You name it. I recently came across one of these journals and spent time reviewing it. That particular one is about seven years old.

Reading it reminded me of many long-forgotten details. I got a glimpse of my entrepreneurial thought process back then. I laughed as I read some of the entries. Some of the challenges I considered big at the time paled in comparison to obstacles I would face years later.

Entries detailing the pros and cons of big decisions I was considering were very revealing. They gave me insight into the way I made decisions then. With the luxury of hindsight, I enjoyed evaluating my former self. I was spot-on about a few things, in the general vicinity for a lot of things, and way off the mark (i.e., wrong) about a ton of things. Looking at my notes, I can see where my logic was flawed when decisions didn’t turn out well. And why it was sound when they did. I can see that my thought processes evolved. I was learning and making better decisions.

As CCAW grew, I stopped writing in my journals. I got really busy, and trying to keep up with a notebook annoyed me. I started using the notes app on my MacBook and iPhone instead. I really regret that. I wish I’d kept writing in my notebooks. And I should have taken more time to review and reflect on my entries. I think that would have supercharged the evolution of my decision making.

If you’re an entrepreneur or are considering entrepreneurship, consider keeping a notebook and reviewing it periodically. You just might accelerate your growth!

Whenever I chat with someone, I enjoy learning about their background. It’s easier to connect if we find we have something in common. Over time, I’ve started to pay attention to something else: I want to understand their journey. I know it sounds odd, so let me explain.

People take notice of where someone is in life—what they’ve accomplished. It’s thought of as evidence of many things. The person is working in ABC position, so they must be of X intelligence or Y caliber. It’s believed to predict the degree of success they’ll reach. There may be some merit to this, but I think there’s a better indicator of future success. How far someone has traveled, metaphorically speaking, to reach their current position is more informative, in my opinion.

For example, Bob and John both graduate top of their class from the same prestigious university. They both receive employment offers from top-tier firms. Most people would think Bob and John having the same odds of success. I disagree. I would like to understand the journey each of them has taken.

Bob attended great K–12 schools. His parents are alums of his college, so he networked with other alums and faculty before he even got there. He joined the same fraternity as his father and chose the same major as his mother. He interned at a company where his mother had worked. He graduated with a stellar GPA and job experience.

John went to public schools with inadequate resources. He doesn’t have any college graduates in his immediate family, so he chose his university by researching those with strong programs in his desired major. He learned about the admissions process and got to know admissions officers by attending conferences in high school. He didn’t join a fraternity. He learned everything about his future profession through his coursework. He networked his way into an internship via career fairs. He too graduated with a stellar GPA and job experience.

Bob and John are at the same place professionally, but John traveled further to get there. He had far fewer resources. John and Bob will both go on to do great things, but I’d bet on John. Given adequate knowledge, relationships, and capital, John has the potential to go further faster than Bob does.

How far someone has come can be a strong indicator of future success. The determination that has served John well so far isn’t likely to go away.

Next time you’re evaluating someone, find out more about their journey. The information you glean may be revealing.

I caught up with a fellow entrepreneur today. We talked about the obstacles we overcame and how our large gaps slowed our progress. We both come from great families, but they’re not entrepreneurial. Not being exposed to entrepreneurship meant we had knowledge gaps. We didn’t know anyone who had the knowledge we lacked or who could open doors to decision makers, so we had relationship gaps. And our families aren’t rich, so we had capital gaps. Because of these gaps (I call them the big three), it took both of us two or three times longer to achieve success than it might have. We’re thankful we made it, but it was a long, rough journey. Now that we have the knowledge, the relationships, and some capital from our first companies, we could build another one much faster.

We also talked about different ways we can help emerging entrepreneurs who are where we were years ago—early in their journey and hampered by the big three. In my opinion, both of us are perfectly positioned to help. I think entrepreneurs with a desire to give back could be amazing investors. Entrepreneurs turned investors can fill the big three gaps and also empathize. They truly understand what early entrepreneurs are going through because they’ve walked in those shoes. Other investors can offer some of this, but the combination of all of it is rare, which is why I believe entrepreneurs can make terrific investors.

Of course, entrepreneurs must learn the nuances of investing in companies to do it successfully, but assuming they do, they’re ideal accelerators of the success of newbies.

If you’re an entrepreneur stymied by the big three, consider reaching out to an experienced entrepreneur in your space and asking them to invest in you!

Today marked the end of my twenty-fourth week of working from home (mostly). Here are my takeaways from week twenty-four:

• Teamwork – I was reminded of the value of working as a team. No one person can be good at everything. But combine people’s individual strengths, and you’ve got a team that is! (Well, good at everything important to you, anyway.)
• Pace – The pace this week was closer to normal.  Busier than I planned, but slower than the past two weeks. I was more intentional about whether and when I scheduled meetings.
• Time blocks – I began blocking out chunks of time on my calendar to focus on bigger things. So far so good. Mornings are still my most productive time.  

Week twenty-four was a good one. No major takeaways this week.    

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

I’m always hearing aspiring entrepreneurs talk about how uncertain they are. They don’t know what they don’t know. They don’t know where to start. They don’t realize it, but this is normal. Uncertainty is a consistent part of the entrepreneurial journey (and life for that matter). Seasoned entrepreneurs will be the first to tell you they’re constantly encountering things they don’t know, questions they can’t answer.

Uncertainty itself won’t hold you back. Lack of action because of uncertainty will. Action is the foundation of entrepreneurship. Getting things done is what sets entrepreneurs apart from the rest of the population. Entrepreneurs don’t just talk, they do something. Do they have a perfect plan for what they’ll do? Usually not. Do they fully understand what they’re tackling? No.

Certainty is as rare for entrepreneurs as it is for everyone else. There’s no clear path to their goal. The way is fuzzy if they can see it at all. But successful entrepreneurs do a few things well to mitigate uncertainty. They determine the direction they want to head. You hear people talk about the vision entrepreneurs have. That’s because they describe to people where they want to be. Next, they start walking in that general direction. They don’t need a smooth or clear path; they just need to know they’re headed the right way (and have a little faith). Something funny happens: the path and the destination become clearer as time passes and they keep moving.

This weekend, I was chatting with someone and he said something that stood out to me. He was talking about starting a new venture. As you can imagine, the pandemic adds a whole new layer of uncertainty. There are lots of things he doesn’t know, but he knows one thing for sure. “I can’t do nothing.” He hit the nail on the head.

If you want to do something great, don’t let uncertainty stop you in your tracks. Keep walking, no matter how small your steps have to be.

Today I had a conversation with a buddy about reflection. He’s thinking of reflecting more and learning about various ways to reflect. He’s looking for the one that suits him best. I’m a huge fan of reflection. Experience is important, but it’s reflecting on that experience that contributes to wisdom. I wasn’t aiming for this when I started writing earlier this year, but my daily posts have become a form of reflection.  

Here’s what I’ve noticed:

• Thinking – Coming up with a topic every day is hard. I’m forced to replay the entire day in my mind. What did I work on? Whom did I speak with? What did I read? I look for the most important thing and then think about it more. I consider it from different angles, do a bit of quick research, mull over relevant past experiences . . . whatever comes to mind. I try to connect less obvious dots and better understand my experiences. I usually (not always) uncover a nugget that becomes the foundation of my post.
• Writing ­– Creating the post is an important part of my daily reflection. It crystallizes my thoughts. It’s one thing to have thoughts in your head. It’s quite another to articulate them logically in writing. Writing helps solidify my learning.  
• Compounding – Identifying the most important thing that happened every day and making small adjustments in my opinions, beliefs, or decision-making is effective. The effect of compounding lots of small changes over time is huge.
• Frequency – I’ve found that daily reflection is ideal for me. The rhythm is perfect. I only have to think back 24 hours. If I had to reconstruct a week or a month I’d be bound to overlook something worthy of reflection.

My approach to reflecting probably won’t work for most people, which is understandable. If you’re interested in the idea of regular, intentional reflection, I encourage you to test a few approaches to find the one that works best for you. It’s something simple that can have a powerful impact!

Today I had an interesting conversation that opened my eyes to a new problem. I was speaking with an entrepreneur who understands transportation better than most. It’s evolving rapidly. I’ll use myself as an example. I used to drive to work every morning like everyone else. And I’d drive on weekends and evenings to check things off my to-do list. Then, a few years ago, I began walking or riding a scooter to work. On weekends I’d use Uber to meet friends. I’d drive to run errands only if I couldn’t walk or take a scooter. My car became only one of many viable transportation options.

As the use of scooters and car sharing surged, infrastructure (roads, sidewalks, street signs, etc.) and planning didn’t change much. Scooter riders had to choose between sharing roads with cars and sharing sidewalks with pedestrians. In fairness, lanes were added in some parts of Atlanta, but not broadly. And it became common for traffic to be held up as Uber or Lyft customers began or ended their rides. Places like the airport and malls made changes but, again, changes weren’t evenly adopted.

As the disconnect between transportation and infrastructure was explained to me, I was amazed. There’s a huge opportunity to bring them back into alignment. Doing so—correctly—could change how we commute forever. Changing physical infrastructure isn’t the likely path—using software and other tools to rethink how we use infrastructure is.

The pandemic has inserted an additional variable into this problem, which isn’t yet fully understood. I believe transportation will change as a result of the pandemic, but I don’t think transportation and infrastructure will be brought back into sync. The pandemic will only increase the disconnect.

The entrepreneur I was speaking with today has a great handle on this problem and a creative solution in mind. I can’t wait to see it in action and find out what effect it will have on transportation.

Today I had a great conversation with an entrepreneur about training. He noticed while working in corporate America that retention is a big problem. Companies spend tons of money educating their employees. They want to introduce the latest and greatest thinking to help their teams be the best they can be. Unfortunately, the employees don’t have time to apply what they’ve learned. More than 90% of knowledge is lost because it isn’t revisited promptly.

I’ve personally experienced this many times. I attend a conference, read an article, or watch something online. The information is great, so I’m excited and can’t wait to put it to use. Then I get back to everyday life. The materials stay bookmarked on my computer or filed in a binder. Usually, I never look at either.

Retention isn’t a new problem, but I think it will become more top of mind for company leaders. With so many people working independently from home, I think companies will be rethinking not only how to promote retention of training but also how to deliver it effectively.

The entrepreneur I talked with has a great idea for a solution and I’m eager to see the customer feedback once he launches an early version of his product.  

Steve Jobs was a great entrepreneur who made a huge impact on society. He changed human communication globally and ushered in a new technological wave. People often refer to his reality distortion field (RDF) when describing his work style and discussing why he was able to achieve such great success. Steve had vision and translated it into successful products. He did what most entrepreneurs aim to do, but at a larger-than-life level.

Entrepreneurs are innovators. Part of innovating is figuring out how to make the impossible possible and convincing others to believe. In some instances it works out. In others it doesn’t. When it works out it’s joyous and amazing. When it doesn’t, it can be crushing, and this is when  it’s more important than ever for entrepreneurs to step up. The team needs it.

I’m not Steve Jobs, but I’ve had my RDF moments. I had a vision for my company, but there were huge obstacles. I convinced our team we could figure out how to push through them. I give them credit for believing and supporting me. Unfortunately, some of those obstacles were insurmountable and we failed. I failed because I underestimated the challenge.

Acknowledging these failures and taking ownership as the leader were some of my biggest learning moments. It was painful and something I hated doing, but I did it anyway. I didn’t realize it at the time, but this was invaluable. By acknowledging my shortcomings, I showed the team that it was OK to not be right all the time. I noticed that when I opened up about what I missed or got wrong, others chimed in with what they’d learned from the experience. It started a reflective team conversation. I view reflection as critical to gaining wisdom.

I also apologized for my shortcomings. My team put so much into these efforts that it was devastating when they didn’t pan out. The apology acknowledged their efforts but also helped us move past the experience as a team. Apologies are simple, but they can be powerful. They can quickly remove the tension from situations.

If you’re working with others on something and it doesn’t go well, consider acknowledging your part in the failure. It’s likely to be painful but also an amazing growth and bonding opportunity!

Adapting has been top of mind for me during the last few months. The world has experienced monumental change in a short time. I’m constantly thinking about how I should adjust to my current reality.

During a conversation last week, Tom shared a professional realization. He has long believed that great partnerships lead to success in his line of work. Therefore, identifying great partners is crucial. He has always established relationships with and evaluated potential partners through in-person interaction. That approach served him well for over a decade. He had a lot of success working with some great people he got to know face to face. Relationships are still key in his world, but in-person dealings aren’t an option anymore. He has to find partners in a new way. He’s actively looking for ways to identify and evaluate partners virtually.

As I reflected on the conversation, a few things jumped out at me. John’s former approach was highly effective but also highly restrictive. He was limited by geographic boundaries. Sure, he could travel and whatnot, but there’s a realistic limit to how often and how far he would travel. I’d imagine there are lots of great people he never considered over the years because they weren’t near him.  

The pandemic has upended life as we knew it, but humans are adaptable and I think it could lead to many amazing things. One in particular strikes me at the moment: opportunities may no longer be geographically constrained. Learning to build relationships, evaluate others, and collaborate virtually could be a game changer. Eliminating spatial boundaries could help spread opportunity more evenly. Qualified people at a geographic disadvantage could have an equal chance to get in the game. The ripple effects could be huge, reshaping our workforce and the economy.

We’re in the early phases of adapting. Lots of questions still must be answered. But the more I think about the potential of virtual work to remove boundaries, the more excited I get. This is a difficult time for everyone, but it could result in seismic change that has a long-lasting positive affect on society.