Today I spent time reflecting on 2020. I read old writings, emails, and text messages. I looked at pictures and news articles. I wanted to digest everything that’s happened this year personally and at a macro level. There was so much to absorb that it was bit overwhelming. I had lots of plans that I scrapped. I wasn’t too thrilled about that but didn’t have much choice. On the flip side, some great things happened that were complete surprises. After all this, I had one big takeaway: Life is iterative and plans go awry. Adjust as necessary.

This was a challenging year, but I feel like it was a year of growth for me. I’m happy to close out 2020 and looking forward to 2021!

Tomorrow’s the last day of 2020, and what a year it’s been. I can’t celebrate New Year’s Eve like I normally do, so I’m thinking about how I want to spend the day. This will likely end up being one of the most eventful years of my life, so I think I’m going to spend time tomorrow reflecting on it. So much has happened that I want to go through and digest it all before I close the chapter. I’ve had a lot of highs and lows this year, so I’m curious how the exercise will turn out.

How do you plan on closing out 2020?

I had a conversation the other day with an entrepreneur (let’s call him “Ed”) who was frustrated with his business partner (“Phil”). Ed is extroverted and focused on the big ideas. Phil is introverted and detail oriented. Ed’s frustration is rooted in feeling like Phil hasn’t been supportive of some of his ideas.

I came to the conclusion that these two are the perfect match. They balance each other’s weaknesses and together are a well-rounded team. The difficulty is Ed’s perspective on the situation. He can’t forget times when Phil has disagreed with ideas he felt strongly about.

Ed and I went through some of their most successful initiatives of 2020 and the role each person played. I pointed out how each of them contributed and how unlikely each success would have been without both of them. Sure, some ideas didn’t pan out, but the ones that did were successful because of the partnership.

In my opinion, in this partnership, Ed has more to be happy about than unhappy about. He just needs to adjust his thinking. Does he want to play team ball or beef up his own stat line? Partnerships are difficult. Sometimes you get your way and sometimes you don’t. In the end, it doesn’t matter as long as you end up wearing the championship ring.

I listened to an exchange the other day that resonated with me. A former entrepreneur who couldn’t get his idea off the ground was talking to a friend.

Former entrepreneur: I used to think I had to be the leader or the ideas guy. I’m starting to realize I’m happier executing someone else’s vision. I like being on teams.

Friend: Really? You always wanted to start your own thing.

Former entrepreneur: I think I just thought that because I was supposed to.

The self-awareness of this person and the circumstances that led to his growth struck me. He has embraced being better suited to be a good team member than the leader. That’s a tough pill to swallow for anyone with an entrepreneurial mindset.

Entrepreneurship is demanding. For many people, it doesn’t work out. If you’re considering it, just know that even if your idea doesn’t fly, it won’t be the end of the world. You’ll learn a lot from making the attempt, and that growth will be priceless. It may be the very reason for your future success.

I had a conversation today with a friend who’s also an entrepreneur. He has a consumer-facing business. He told me about a difficult customer who has unrealistic expectations on a shoestring budget. I had this exact same situation many times in the early days of CCAW. We tried to work with customers who had tight budgets and priced our products aggressively. In the end, we accomplished our goal of attracting more customers. What I didn’t realize was that some of them weren’t a good fit for our business. The time and energy required to service these new customers skyrocketed. Many of them were unprofitable and impossible to please.

As CCAW grew and we had more resources, we developed a more sophisticated pricing strategy and implemented it in a dynamic pricing engine. The strategy was aimed at attracting customers who wanted a fair price but also wanted high-level customer service. These customers were OK with paying a little more for peace of mind. Over time, our data told us they were also more agreeable and easier to work with when unavoidable circumstances arose (e.g., bad weather). We ended up building a large profitable business by targeting this type of customer.  

When you’re starting out, you’re figuring out how to solve a problem in a way that people are willing to pay for. Once you do, it’s worth stepping back and thinking about whom you want as customers. You can’t be everything to everybody. All revenue isn’t good revenue. If you’re intentional about the customers you want to serve, you can steer clear of those who aren’t a good fit—who, frankly, are more trouble than they’re worth—and build customer loyalty.

Yesterday was a unique Christmas, to say the least. Many people couldn’t get together with friends and family the way they usually do. There was a silver lining, though. I assume because they couldn’t do “Christmas as usual,” lots more people reached out to me than normally do at Christmas. I had some great phone conversations and FaceTime calls that I really enjoyed.

Christmas may be over, but we’re still in the holiday season. If you think about someone, reach out. I’m sure they’ll appreciate the gesture. Who doesn’t like being reminded that someone cares about them and is thinking of them? You never know: you might just make their day!

Merry Christmas!

I hope everyone had a safe and healthy holiday!

Tomorrow is Christmas, my favorite holiday. The one I most associate with spending quality time with family and friends. It’s also a reminder that the year is coming to a close. Over the past few years it’s become more significant to me, and I completely unplug and stop working from Christmas Eve through New Year’s Day. This allows me to be present with family and friends.

It’s been an eventful year. Many people have experienced unimaginable pain and suffering. I hope that tomorrow can be the bright spot of 2020 and everyone is able to enjoy the holiday.

Merry Christmas and enjoy your downtime with the people you care about!

Today I had a conversation with the leader of an innovative company. They had a really cool technology and counted some well-known organizations as customers. Unfortunately, the pandemic caused their customers deep distress and made their business model unsustainable for the foreseeable future. Though he did everything in his power, he wasn’t able to right the ship. I was struck by how upbeat this leader is. He seems at peace with the fact that the company won’t survive. He’s not dwelling on their bad luck. Instead, he’s making sure his team is treated fairly and has a safe landing.

Sadly, there are far too many of these stories this year; 2020 will go down as one of the most challenging years ever for many founders and other leaders. When you’re in the midst of pain, it can sometimes feel paralyzing. While we’re still grappling with everything that happened this year, it’s important for leaders and team members to remember this: painful periods always pass. Look for the light at the end of the tunnel instead of dwelling on the fact that you’re in a dark tunnel. Tough situations have an end, and you should train your energy on getting to it. Once you’re there, you can take as much time as you want to reflect.

Every founder I know has had to endure bad situations. Over the years, I’ve been humbled by mine. (Some were downright awful.) Each time, I tried to keep a positive attitude and focus on getting through the situation rather than dwell on its dreadfulness. Some of them resolved quickly, while others played out over the better part of a year. Either way, focusing on getting to the end was one of the biggest reasons I was able to weather the storm.

As we approach the end of 2020 and look to an uncertain future, just remember: In the end, it’s going to be OK.

I caught up with a buddy today to discuss an opportunity he’s evaluating. He said he knows he says yes to too many things, often too quickly, and that he’s looking for another perspective before deciding. I’ve known him for years, and I agreed with him. His self-awareness impressed me and made our conversation about his opportunity more substantive. I realized that he and I are opposites, which is likely why he called me. I quickly say no to most things and am slow to say yes to things I’m interested in as I evaluate them.

Being self-aware is difficult but valuable. It helps you understand the areas you can improve upon (your weaknesses) and those you should lean into (your strengths). My conversation today was a timely reminder that in 2021, I want to do a better job jumping on good opportunities that interest me. My habits won’t change overnight, so my plan is to recruit the perspectives of people who recognize good opportunities and are good at saying yes quickly.

I’m glad I connected with my buddy today. Our opposite styles are complementary, which is valuable to both of us. In the end, we agreed to balance each other in 2021. I’m looking forward to that!