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Life Lessons

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Weather the Storm with Small Wins

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!

Living in the Present

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.

Everyone Needs Downtime

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!

Like It or Not, Times Change

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.

Not Recognizing Greatness Hurt Me

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!

What Will Your Epitaph Say?

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?

Sometimes the Universe Doesn’t Like Your Plan

I caught up with a founder who shared his recent lessons learned. The pandemic forced him to shift his in-person educational events to Zoom. The lack of personal interaction initially concerned him. He worried about his customers not being able to interact and build relationships. In the end, he didn’t have a choice, so he decided to make the best of it. Soon, he realized he had an unexpected chance to capture content. He recorded the Zoom sessions and is building a content library and supporting marketing materials. He will offer the content to future customers as well as those he has now.

His story reminded me why he’s an entrepreneur. His positive attitude helped him adapt to a bad situation. Because he sees his glass as half full, he recognized an amazing opportunity and took advantage of it. I loved his outlook and approach. In the end, he exceeded his pre-pandemic expectations.

Sometimes the best-laid plans go awry. It happens to all of us. You did everything you were supposed to, but it wasn’t meant to be. Some things are out of our control. But these hiccups don’t determine whether we ultimately succeed or fail. In my opinion, perspective and response do. How we respond to adversity is 100% within our control. Our response is usually a reflection of our perspective. If we believe the cloud we’re under has a silver lining, chances are we’ll find it.

Next time things don’t go as planned, don’t fret. Consider what you can do to make something good happen.

What I Learned About My Motivations

What motivates an entrepreneur is important. The journey is tough and full of emotional highs and lows, and it usually takes many years. The right motivations help you make it to the finish line. Yesterday I wrote about my why, which is one of my motivators as an entrepreneur.

I’ve noticed a few things about my motivations over the years. I can have more than one at a time. But one—my why—always dwarfs the others. It’s usually the only one that I have strong convictions about. Historically, I’ve been happier with decisions based on it. I call it my one-to-one rule, and it simplifies my decision-making and how I move forward. When I’ve made decisions to satisfy more than one motivation, it just hasn’t turned out as well.

My motivations change over time. I originally was passionate about helping automotive consumers because I was a car enthusiast (still am). Now, it’s helping entrepreneurs (small and medium-sized businesses). Why? Material things matter less as I mature. I still love cars, but not as much as I love people. These days, I’m motivated to help people I can relate to.

Motivations are important. They helped me stay the course during my entrepreneurial journey. Do you know what motivates you?

Action Drives Change

I recently had a conversation with an aspiring entrepreneur. She’s passionate about an idea and has the technical training to execute it. She asked my opinion on various things, which I happily gave. But she still wasn’t quite sure what to do next. I asked, “What’s the single most important thing you can do right now?” She named something. I suggested she start by taking action on that one thing.

As we talked, I thought about my journey as an entrepreneur. Early on, I was full of ideas and didn’t know where to start. When I was working with others, we could talk endlessly. Sometimes the sheer number of possibilities felt paralyzing. Indeed, sometimes I was paralyzed. Over time, I learned that one thing matters: action. It was action that would change a situation. It was action that would turn my vision into a reality. It was action that would separate us from others. At a certain point, I had to stop talking and start doing.

That lesson took me years to learn, but I’m glad I did. Taking action on something, even when the way forward isn’t 100% clear, has been my key to progress. It changed my life.

I’m encouraged by the positive conversations we’re having as a nation about race and police brutality. They’re overdue and they’re helping us gain the understanding of one another that we so badly need. As you have these conversations, consider asking yourself a simple question after each one: “What action am I going to take now?”

What 90 Posts Have Taught Me

Today marks my ninetieth consecutive day of sharing my thoughts in posts. (I previously described how this started.) I recently spoke with a peer about my experience. He’s considering doing it too and wanted to ask me a few questions. By the time we finished chatting, I had had an epiphany: I understand things better when I share my thoughts widely.

I tend to think deeply about things. I try to understand by identifying connections that aren’t obvious. I used to ruminate and perhaps talk with one or two people very close to me. That approach was flawed. It didn’t help me achieve my ultimate goal: understanding.

It was a mistake to not share my thoughts or to do so only with a few like-minded people. I avoided opening up to others with different perspectives who would test my thinking or point out my blind spots (we all have them). I wasn’t really trying to understand, because I wasn’t talking to people who would be likelier to disagree with me. Naturally, I saw things only through the lens of my life experiences. My reality. I would come to understand an issue, or think I did, but since I looked at it only from my own narrow angle, I ended up missing things.

Sharing my thoughts broadly invites feedback. It sparks great conversations—opportunities for me to listen. I get glimpses of other people’s realities. I see things from their angle! I’ve learned that truly understanding something means getting as close as possible to a 360-degree view of it. The more people I talk to who are different from me, the closer I get to that goal.

Sharing my thoughts daily has illuminated all of this. Sometimes my initial thinking is wrong. (Whose isn’t?) When I share my thoughts with the world, I’m inviting others to help me acquire true understanding. Each person bridges a gap in that 360-degree circle.

I didn’t envision understanding things better as a benefit of sharing when I began posting every day, but it is, and I’m thankful for it.

I encourage everyone to share their thoughts more widely. It doesn’t have to be through writing; do it in a way that works for you. When you get feedback, listen. You’ll understand things much better.