I shared my transition to venture capital the other day. Since then, I’ve talked with several people about the details. (I’m happy to share, listen, and help however I can.) I’ve noticed a pattern. A lot of people are contemplating or already going through serious life transitions. Professionally, personally—you name it; big changes are happening or on the horizon for many folks. The pandemic surely plays a big role in this. The abrupt change forced us to experience something different. Many are now considering what parts of this change they want to make permanent. And I’m sure there are a host of other reasons too.

I personally think the key to navigating change is being adaptable. Don’t get me wrong; I’m not saying to go wherever the wind takes you. I personally try to evaluate and then embrace the change and make it work for me (if that’s possible). I’ve learned to not make the past my baseline. Instead, I try to accept my current reality, which, admittedly, is sometimes easier said than done. All this helps me to adapt in a way that works for me.

Regardless of how you go about navigating change, be adaptable and do it in an way that works for you. And remember there are lots of other people considering or going though something similar. You are not alone.

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 a conversation with a friend. He’s questioning himself even though he’s successful. Are my peers passing me up? Should I be striving for more? Why don’t I have the life others have? He’s comparing himself to people who appear to be more successful.

When I was building CCAW, there was a time in 2011–2012 when I compared myself to other founders and kept score. Am I growing as fast as my peers? Who will reach $1 million in annual revenue first? Why didn’t I think to do X? Why haven’t we implemented Y? This period was short-lived. I thought through things and realized the following:

• Industry – CCAW operated in an industry that resisted change. And I bootstrapped the company, so we had to be capital efficient. Leaning on partners to warehouse products and fulfill our orders was a capital-efficient model. We were attached to their hips for better or worse. We had lots of great ideas but couldn’t execute them without partner buy-in. Our growth was heavily affected by our partners’ willingness to embrace change. They often did so only slowly, after years of conversations.
• Gaps – My peers all had different backgrounds. Some came from entrepreneurial families. Some had worked in startups before. Others were starting their second or third company. I was from a family of folks who worked for other people, I’d worked in the corporate world, and I was building my first company. They had entrepreneurial knowledge gaps—I had chasms. It took time to learn what I didn’t know, so my path to success was longer.
• Outside looking in – You never know someone’s full story. Their life may look great, but they could be in debt up to their eyeballs or miserable in myriad other ways. Lots of people fake it till they make it (or don’t make it). It’s foolish to make yourself unhappy by comparing your life, which you know well, to someone else’s facade.

I learned early in the CCAW journey to focus on what was right for my company and me. I acknowledged that my background and circumstances were different than those of my peers. Some things I would never do, or I’d do them at a slower pace. And that was OK. I supported and congratulated my peers on their accomplishments. I tried to focus on our successes instead of dwell on the things we hadn’t accomplished. Life is better when you see the glass as half full.

Comparisons are bad for your mental health. Unfortunately, many people compare themselves to others at some point. If you find yourself falling into that trap, give yourself credit for your accomplishments and recall Teddy Roosevelt’s wisdom: “Comparison is the thief of joy.”

Today I caught up with a family member. One of the things we talked about was my habit of posting daily. Bob asked how long I’d been writing, how long I planned to write, and why I had decided to write every day. I told him that I’ve been writing for four months and that I plan to do it for at least a year (hopefully much longer) and explained my reasons. I get asked these questions a lot. Most people say, “That’s nice to know,” and the conversation moves on. Today was different.

Bob shared how my posts have affected him. I really enjoyed the feedback after writing every day for months with little idea of whether I’m doing anything other than whistling in the wind. Bob said he reads my posts every day on LinkedIn’s app. LinkedIn doesn’t provide stats on article impressions or views, so this was news to me. And he said that he has shared some of my posts. With no stats, I had no idea if I’d gotten any shares. Then he told me how my weekly work-from-home posts have helped him manage better. Those are the posts in which I track how many weeks I’ve worked from home (sadly, it’s been eighteen), describe my main observations during the week, and summarize my takeaways. I assumed this post didn’t resonate with others. It was designed to force me to reflect every week and be aware of the pandemic’s impact on my mental state and to be my “easy” post for the week. I thought it would bore people.

I found out that Bob has enjoyed my reflections so much that he’s borrowed the idea. He now reflects about things himself, both alone and with his team. They have a standing virtual conversation that’s become the highlight of their week. They share personal and professional thoughts and open up about their mental state. It’s become a substitute for lost water-cooler talk and brought the team closer.

My conversation with Bob was eye-opening, to say the least. Never in a million years would I have guessed that my posts had helped a team connect. Or that anyone reads them every day. When I began writing, it was to give back and help others by sharing my experiences and thoughts. I reflected on what I’d learned after 60 days. Today, I learned more. Bob helped me understand the reach of my writing and the impact it can have. I’m glad my posts add value to others’ lives, grateful for the experiences and opportunities that I’ve been blessed with, and encouraged to continue writing.

Next time you’re considering doing something positive for others but aren’t sure if it will be helpful . . . do it anyway. You could end up having a much bigger impact than you ever could have imagined!

I’ve been working with an entrepreneur for two months. She’s a developer with an app idea who could never find time to create an MVP to test her idea. We settled on a weekly cadence: she would email a group of advisors about her progress and ask for assistance if she needed it. The plan was simple but gave her the encouragement and accountability she needed to execute on her idea.

All was well for the first six weeks. In week seven, the pandemic affected her personally. She wasn’t able to focus and stopped sending the updates. She had stopped working on her app altogether. This was a huge red flag to me.

After hearing about everything she was juggling and her desire to make the app a reality, I made a recommendation: focus on one thing you can accomplish in a day or two. It doesn’t matter how small it is—it can be anything that moves you closer to your goal. Repeat every few days. The idea was that she could continue making progress while dealing with other responsibilities, and she’d have wins she could celebrate.

Sometimes even the best plans go awry. Life happens. It’s just the way the world works. At CCAW, there were many times when I felt like everything was going wrong at once. It was paralyzing and discouraging. Over time, I learned a few things:

• Focus on what you can control. Don’t dwell on things outside your control.
• Figure out how to keep making some kind of progress in small chunks. Celebrating small wins can change your perspective and give you a much-needed spark.
• Talk to credible people about what you’re experiencing. Keeping your feelings bottled up isn’t healthy. You’ll find that other people have been through similar things and can convince you there’s light at the end of the tunnel.
• No success story is up and to the right all the time. There’s always a period of struggle. This too shall pass.

The next time life prevents you from accomplishing your goals, find one small thing you can do quickly. And do it again in a day or two. Small wins will help you weather the storm!

I’ve always been in the habit of asking myself a question: am I doing what I need to be doing? Lately, I’ve struggled to answer it. I usually compare what I’m doing today to what’s worked for me in the past. In recent months, I’ve compared what I’m doing today to what I did before COVID-19. I lifted weights four or five days a week to release stress and stay healthy. I traveled by plane every few weeks to maintain existing relationships and build new ones. I went to the office every day to focus on work. I ate out often because I was busy.

When the past is my baseline, the answer is no, I’m not doing what I need to be doing. It’s not that I don’t want to do these activities. I do, but I’m just not comfortable doing them in this environment. That got me thinking about my approach. Should the past be my baseline?

The world has changed so much over the last few months. Many things that were commonplace aren’t viable today. I decided that using a comparison that isn’t feasible doesn’t make sense. In fact, I think it’s unhealthy.

I’ve started to ask myself a different question: am I doing what I need to be doing in the current environment? I no longer use the past as a baseline. What matters is whether I’m getting what I need in the best way possible given the current reality. For example, I need to relieve stress and stay healthy. I’m not comfortable going to the gym, so weightlifting is out. Instead, I’m running outside. Well, it rains pretty often, so I don’t consistently run four or five days a week. Two or three days is more realistic. Since I’m not as active, I now eat home-cooked meals to keep calories down (take-out is full of them!).

Is running two or three days a week what I’m used to? No. Does it give me the same results as my old workout? No. Are running and eating home-cooked meals what I need to be doing now to stay healthy and relieve stress? Yes.

I realized that benchmarking my life against the past was doing myself a disservice. I couldn’t fully embrace the present—which, after all, is all I’ve got—because a part of me was always holding on to the past.

Next time you’re grading yourself, consider thinking about what you need now, in today’s circumstances. You may realize you’ve been shortchanging yourself.

I spent over a decade building CCAW. The journey was pretty crazy—filled with extreme highs and lows. I didn’t realize the value in taking time away. I worked five years straight before taking a one-week vacation and around eight or nine years before taking a two-week one. It took people close to me encouraging me to take time off and feeling mentally and physically exhausted.

On vacation, I didn’t look at work unless it was an absolute emergency. I made sure to communicate this to the team to set expectations.

I hadn’t realized how wound up I was. Time away brought this into focus. I worked out regularly, so I had a physical release, but this was mental. It took me longer than it should have to relax and enjoy my downtime. Working on something intensely for so long had slowly changed my mental state and I hadn’t realized it. Time away let me reset mentally and relax.

It’s common knowledge in my entrepreneurial circles that sleep is a challenge. A fair number of us don’t sleep soundly because our minds are racing. Waking in the middle of the night becomes the norm. We learn to function on suboptimal sleep. I slept much better on vacation, recharging mentally and physically.

I come up with many of my best ideas and solutions to nagging problems when I’m away from the business (like some people say they do in the shower!). I’ll be thinking about something else and an idea will pop into my head. I jot it down so I won’t keep thinking about it. Over the years I’ve noticed that when I get things out of my head, my subconscious mind uses the bandwidth in creative ways.

My experiences with time away are probably extreme, but I share them so others can learn from them. You may think there’s no good time to be away from your business, but sometimes that’s exactly what you and the business need.

I hope everyone enjoyed their downtime this holiday weekend!

Today I had a conversation about change. Sarah is experiencing significant change, like everyone, as a result of COVID-19. She’s feeling a lot of angst. She wanted to know how I’m dealing with virus-related changes and what I’ve learned from navigating change over a decade as an entrepreneur.

The first thing I noticed is that Sarah rejects change. She fights it if she didn’t initiate it. She will change eventually, but only after the pain of not doing so is unbearable. But change can be caused by something out of our control (like a pandemic). Fighting against something you can’t control wastes time and energy. The world doesn’t care what we think. We can either accept change and get on with things or struggle against it and endure anxiety, or worse. Regardless, the change keeps happening.

I also noticed that Sarah sees most change as an obstacle. That’s her perspective, for whatever reason, and it affects how she copes. It would help her to realize that while change is inconvenient, it opens up new possibilities. Thinking about them instead of dwelling on present discomfort can illuminate opportunity.

I view change as inevitable. The world is constantly evolving. That has always been true and it may be the only thing that will never change. With that perspective, I try to embrace most change. Doing so has allowed me to take advantage of some great opportunities and spared me avoidable stress.

The next time you experience change (now, maybe?), consider accepting it and focusing on the opportunities it presents.

One thing I didn’t do well early in my career was recognize greatness quickly. Someone close to me had to point it out (much later, typically). People . . . opportunities . . . accomplishments—it didn’t matter. For whatever reason, I wouldn’t see it as soon as other people did. And when I did, sometimes it was too late.

During my journey building CCAW, I realized that I didn’t recognize greatness quickly. I didn’t like this about myself and decided to change it. My knowledge gap was my first issue. I tackled it by reading widely in areas I deemed important personally and professionally. This gave me a baseline. When something was superior to that baseline, I could readily identify its greatness. My personality was another obstacle. I tend to be laid back and have blind spots when it comes to people. I can’t change how I’m wired, so this was more challenging to solve. I learned to ask the opinions of colleagues or friends who deeply understand people when I encountered someone I wasn’t sure about. Their observations helped me recognize when the person was great. Not the most scientific approach, but it works for me.

Not being able to recognize greatness hindered me in a few ways. It slowed my decision making, so I missed out on some great opportunities. And I didn’t allocate the appropriate time and resources to great people and opportunities.

Times change. Today I had a conversation with a buddy about an investment I made that has done well. He asked how I knew the company would succeed before other people did. I told him that I quickly recognized its uniqueness because I’ve seen lots of companies in the space and done lots of reading about the space. This company’s performance was rare when I baselined it against what I usually see. I believed this company was great and invested in it confidently.

Some opportunities really do come along only once in a lifetime. Learning to know them when you seem them can be life changing!

Years ago I read a post by Steve Blank that stuck with me. Steve is a serial entrepreneur, author, and professor at Stanford, Berkeley, and other schools. He’s a very credible person when it comes to entrepreneurship. Today I thought about the post and read it again. It’s titled Epitaph for an Entrepreneur, and it reflects on his entrepreneurial journey. In it, he shares things he learned about balancing his personal and professional lives.

One thing I took away from it was Steve’s evolution from a philosophy of “live to work” to one of “work to live.” I can relate. When I started CCAW, I went all in. I worked lots of hours and didn’t have much time for anything else. It was success or bust. Work was my life. Well, CCAW was successful and now I’ve entered a new phase. Not quite the same as Steve’s, though. Now, I work to help others be successful. My hope is that they will do the same when they can, creating a flywheel of sorts over time. I also work to enjoy experiences and time with people I care about. Tomorrow isn’t promised, so we have to make the most of today. I guess I work to live now—or at least I’m moving toward it.

Steve’s post is insightful and thought-provoking. It shows how the entrepreneurial journey (and life for that matter) evolves over time.

This life isn’t practice for the next one. Steve decided that he would prefer his epitaph to say, “He was a great father” rather than “He never missed a meeting.” What will your epitaph say?