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Life Lessons

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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.

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Time

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.  

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Mindset Matters to Outsize Success

In my post yesterday, I shared my thoughts about success requiring not only luck (preparation + opportunity) but also the ability to recognize an opportunity and the willingness to act on it despite the risks inherent in doing so.

Today I had a chat with a close friend about people’s mindsets. We talked about how important mindset is to outsize success. Your mindset can prevent you from taking action when you get a lucky break—even when it’s staring you in the face.

I’ve noticed a pattern in the mindsets of people who’ve achieved big successes. They realize they could fail. The time and energy—not to mention money—they put into something could be all for nothing. Yet they don’t dwell on that. They accept it and focus on the upside potential. If everything goes right, how big could this be? They look for opportunities that have massive upside.

The next time you get a lucky break or evaluate an opportunity, be aware of your mindset. (In other words, think about how you’re thinking . . . something, it’s believed, humans are uniquely able to do.) Take a second to ask yourself: if everything goes right, how big could the upside on this opportunity be? The change in mindset could lead you to outsize success!

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Goodbye 2020

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!

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New Year’s Eve Plan: Pandemic Style

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?


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Opposing Perspectives

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!

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Close the Loop

Over the years, I’ve been humbled. I used to think I was superhuman—capable of doing anything. Now I recognize that I’m not good at everything, nor do I have the experience to navigate certain situations. I’ve learned to ask for help. Learning from the experiences of others has been invaluable in challenging times. If I’d done it more in those early years, it would’ve saved me tons of time and energy. I encourage early founders to learn from my experience.

Learning from others isn’t a one-time thing. It requires investing in and maintaining relationships. I’m a big believer in healthy relationships being bidirectional. As an early startup founder, it doesn’t feel like you have much to offer people who are sharing their wisdom with you. That may be true, but you can do one important that they’ll appreciate: close the loop. When you ask people for help or advice, follow back up with them to let them know the outcome. Good, bad, or ugly. They’ll appreciate the effort.

I sometimes fall short, but I do my best to close the loop. I appreciate and respect other people’s time, and I make sure to thank them when I close the loop. Simple to say, simple to do—but powerful. It will strengthen your relationships.

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Time and Space to Think

Yesterday, I shared what I learned from Inside Bill’s Brain: Decoding Bill Gates. I don’t watch much TV, but this was an insightful series. Today I’ve been thinking about Bill’s “think weeks.” He regularly spends a week alone in a cabin reading and thinking. The quietude and stillness give him an optimal environment for his best thinking, allowing him to distill things and solve complex problems.

Bill’s intelligence and ability to rapidly comprehend things have been remarkable all his life. (His siblings, coworkers, and wife all confirmed this.) And they’re at their highest level when he reduces his activity level and just thinks.

I started to wonder what environment allows me to do my best thinking. I usually need to get in the zone to think about complex things. Big blocks of time let me do that, and then I can concentrate and make significant progress on a problem. Once I see progress, I get excited and want to keep going. Interruptions or lots of activity around me are disruptive, so I try to be somewhere quiet and still when I need to get in the zone. I’ve also learned that writing helps me make connections and solve complex problems. It forces me to organize and communicate my scattered thoughts in a way others can understand.

This year has been challenging, to say the least. Like everyone, I’m ready for it to be over. In tough situations, I try to look for the silver lining. I believe life is about perspective and there’s always something positive; you just have to look for it. This year is no exception. Less activity and a slower-paced life because of the pandemic have given me more time to think than I’ve ever had. I’ve accomplished things I’ve been putting off for years (like blogging) and worked through some tough problems. Bill Gates does think weeks. I’ve sort of done a think year.

Bill Gates is a brilliant person who made an impact on society through entrepreneurship and is doing it again through philanthropy. I love learning from the experiences of people smarter than me, like Bill. There’s a lot to be said for his practice of taking week-long blocks of time to think. (If someone of his stature continues to prioritize this, there must be something to it!) I don’t have the luxury of doing think weeks, but I’ll work toward being more intentional about taking time to read and think in the right environment.  

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Unplug and Give Thanks

Tomorrow is Thanksgiving, a holiday that’s special to me. When I decided to quit corporate America and start a company, I broke the news to my parents over a Thanksgiving holiday. In the early years, the holiday was an opportunity for me to make progress on big projects. Eventually, though, it dawned on me what a terrible way of doing things that was, and I began enjoying the day with people I loved.

Unplugging was something I struggled with for a long time. I was worried about failing, so work issues were always racing through my mind. I eventually realized there weren’t many weekdays when I could mentally disconnect and learned to set work aside when they came around. Thanksgiving was definitely one of those days. I also found it to be a great time to reflect and give thanks for everything that had gone right that year.

Have a great Thanksgiving and enjoy your downtime with people you care about!

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What I Least Expected to Gain

I was talking with an early entrepreneur, who asked a great question. “What’s the most meaningful thing you gained from your journey that you least expected?” Now, I admit . . . I was totally stumped. I needed time to answer. I wanted to think about it so I could give an authentic response. Toward the end of our conversation, it came to me: friends who understand me and experienced the struggle too.

Being an entrepreneur is hard. You’re trying to do the impossible with limited resources. You’re pushing yourself and your team to the limit. It’s not something that most people understand or can relate to. I had a great support system of friends and family before I founded my company. I was able to talk with them about most things in my life. But when I became a founder, that changed. I was experiencing things they hadn’t and that they couldn’t relate to. After a while, I steered conversations with them away from work. My company was an outsized part of my life, so I found myself on an island without anyone to talk to who could relate.

I eventually connected with other entrepreneurs at a similar stage and this changed. All of a sudden, I could talk to people who got it. They were problem solvers facing the same challenges I was, and they had crazy visions that others in their life couldn’t understand. Over the years, those peers became wonderful friends. The friendship dynamics are hard to explain, but because we supported each other during some of our toughest times, the bonds are tight.

When I decided to start my company, I wanted it to be a success and I wanted to enjoy everything that came with it. I achieved success, but the thing that stands out more than that are the friendships I formed with other entrepreneurs. We come from different backgrounds, but we bonded over our shared desire to solve tough problems by building amazing companies. Companies can be bought and sold, but true friendships like these are invaluable.

If you’re looking to do something great (even if it’s not entrepreneurship), consider connecting with others who are traveling a similar road. No matter how great your accomplishments, the friendships you’ll build along the way will be priceless.

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