Early in my founder journey, I had an overwhelming feeling that I had to have all the answers. I felt like it was expected of me. Whenever the team asked a question, especially about direction, I thought I should know the answer. I worried that they would lose confidence in me if I didn’t. As I worked with suppliers, it was the same. I felt like I had to have an answer or they would look at CCAW differently. Even when speaking with entrepreneurial peers, I felt the same self-imposed pressure. It was ludicrous.

As I settled into running a company and leading a team, I became more self-aware (partly through reflection on failures and partly from people pointing out my shortcomings). I realized there were things I was really good at and felt confident answering questions about. Other things I was inexperienced in or just plain bad at, and I wasn’t well equipped to answer questions about them. As I matured, I stopped trying to come up with a good-sounding answer that would let me squirm out of the corner I was in when the true answer was “I don’t know.”

Those three words are simple, powerful, and scary all at the same time. They’re scary because you’re admitting you have a knowledge gap. This can feel uncomfortable (it was for me), but it helps to think of saying them as acknowledging that you’re human. They’re powerful because they signal self-awareness, confidence, and honesty, and they give you the opportunity to learn something. And they’re simple because . . . well . . . they’re only three words.

Nowadays, when I’m asked about something outside my wheelhouse, I usually admit my ignorance (I still slip up, though). I try to turn it into an opportunity to learn. Usually I say something like, “Honestly, I’m not sure, but I’m actively seeking different perspectives on this. I’d love to hear yours.” People will tell me what they think, which adds to my fund of knowledge. Or they’ll admit they don’t know either, which reassures me that I’m not the only one.

When I speak with entrepreneurs now, I try to tell them what I wish someone had told me early on. It’s OK to not know. In fact, it’s normal. You’re human and no one expects you to have all the answers!

At CCAW, I was always thinking about making the company better. How can we make our customers’ experience better? How can we make it easier for our vendors to do business with us? How can we use technology to improve internal operations and make life easier for our team members? It was a relentless decade-long quest to be better. It definitely worked. We built an amazing company and some pretty cool technology. Admittedly, I pushed extremely hard (sometimes harder than my team thought I should!). In my mind, there were all these ways we could be better and I wanted to attack them! I wanted us to reach our full potential.

One day I had a conversation with my mom that put things in perspective. She reminded me of where it all started and who helped me. In the early days of CCAW, I stored product at my parents’ house (and other places too). My mom constantly asked me, “When are you going to get all these boxes out of my house? This isn’t a warehouse, Jermaine!” My parents lived in Louisiana and I was in Atlanta (or wherever EY had dispatched me for the week). I used spreadsheets to track the product I was storing and manage customer fulfillment. When we sold product, I would get on the phone and coordinate with my Dad to get it to customers. The stuff was heavy and bulky. He usually made time to ship stuff after working a grueling day in the sun at a refinery. Without his help, there’s no way I would have been able to get CCAW off the ground. I’m super appreciative of that help—and of him for putting up with me.

That conversation with my mom stopped me in my tracks. I realized that instead of focusing all the time on making improvements, I should recognize how far I’d come and how other people helped me get there. At the time of that conversation, we were probably doing around $7 million in annual revenue. We had built a completely automated system that fulfilled hundreds of daily orders from dozens of warehouses nationwide. Yes, there were still warts on the business, but it had come a long way.

From Mom, I learned that things will never be perfect and there will always be things you can improve. It’s important to remember to acknowledge how far you’ve come and the people who helped you get there (thanks Dad!).

How far have you come? Who helped you along the way?

After I published yesterday’s post, I remembered another question from Friday’s Q&A session that stood out to me:

How do you push through when you’re having a bad day?

Someone who asks this in an open forum is probably seriously struggling with the issue. And there are probably ten more people experiencing something similar but suffering in silence. For this reason, I felt it was an important question to take seriously. I answered it Friday during the session, and I’m addressing it again in this post.

The most important thing for entrepreneurs to understand is that they’re human beings. They’re not superhuman or indestructible. They experience the same emotions as everyone else. And like everyone, they have bad days. It’s OK to have an off day. In fact, it’s normal. When entrepreneurs have an off day, they should be honest with themselves and acknowledge what they’re experiencing. Sounds simple and maybe even stupid, but it’s important. Being honest with yourself is the first step in dealing with a bad day.

Then you can be honest with others. I’ve written about this: support systems are critical to entrepreneurial success and mental wellness. Bad days are one reason that’s true. If there’s someone you trust to act as a sounding board, you can talk with them to work through what happened, and why. Such conversations often help you let go of the troubles of the day and move forward.

Even if you’re having a bad day, stuff still needs to get done. Retail stores don’t close because the staff is having a bad day. You won’t have sympathy for your HR department if your paycheck is late because someone had a bad day. What things do you have to get done, regardless? Create a system under which you’ll be held accountable. There are lots of easy ways to do this. Email updates are a simple approach with numerous benefits. Another effective tool is a daily team huddle or stand-up meeting. Any of these can unlock the power of accountability. I credit accountability for some of my more successful periods. Avoiding it is a huge mistake that many early entrepreneurs make (I know I did).

Everyone has bad days. The key is to recognize one and take steps to turn it around in time to prevent a bad day from turning into a bad couple of days or a bad week.

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!