An elder once told me, “You can have whatever you want, but you can’t have it all at once.” I didn’t appreciate the wisdom in that statement back then, but I do now. I learned how right he was from some painful experiences. People have a finite amount of time and energy, so accomplishing an infinite list of things at any given time isn’t realistic. Prioritization is the key.

Here are a few things I’ve learned about prioritizing over the years:

• Start with the end in mind – I first try to determine where I want to end up or at least the direction to head in. This compass helps me when I’m struggling to prioritize.
• Time sensitivity – If something is time sensitive or its window of opportunity is closing, I try to assign it a higher priority. Everything isn’t time sensitive.
• Things will drop off – Some stuff won’t make the cut and that’s OK. If I know something won’t get done because it isn’t one of my priorities, I try to communicate that to anyone else who’s involved.
• Small number of priorities – I do best when I have a list of three to five priorities. More than that and I’m less effective.
• Impact on others – I’ve caused and been on the receiving end of collateral damage when too many things are forced at once. When you don’t prioritize, others can be affected as much as or more than you are.

I’m still a work in progress. I haven’t mastered prioritization yet, but it’s become a little easier now than I’ve learned these things. I hope you’ll find them helpful too.

Today I had a great conversation with a founder friend that reminded me of something. The journey of a founder is an evolution. The needs and priorities of a founder will change.

Founders who build successful companies often end up selling them. What then? Many struggle to decide what they want the answer to that question to be. Do they start over with another company? Do they retire to a tropical island? Do they use their experience and skills to re-focus their efforts on giving back?

And it’s not just their professional lives—all aspects of a founder’s life evolve. I was 100% focused on CCAW as an early founder. I worked all-nighters and prioritized CCAW’s success above most other things. I don’t recommend that approach, but it’s what I did. As I’ve gained more experience, a lot has changed. I don’t do all-nighters anymore. My brain and body don’t respond to them like they used to. My priorities have also changed. Family and friends rank higher than professional success. And how I define success has even changed. I now think of success as helping others reach their full potential as opposed to building my own successful company. As I continue to live, I’m sure more changes will come.

Evolution is part of life. From my experience, it’s important for founders to recognize this evolution, embrace what comes from it, and adjust accordingly. I didn’t recognize that my needs and priorities were changing—I carried on with the same approach, the same habits. It took life slapping me in the face to change and make a ton of adjustments quickly. I wish that I’d taken time to regularly reflect on this and make gradual adjustments periodically. Now, I plan to reflect annually during the Christmas holidays. It’s a perfect time to think about the past year and the one coming next.

Founders should begin their journey with the understanding that who they are now probably isn’t who they will always be. This will make it easier to recognize their evolution, process it emotionally over time, make practical decisions, and implement changes gradually. Life never stands still!

I caught up with a good friend yesterday. He’s an entrepreneur who has attained what I consider to be an elite level of success. He said something that stuck with me. Business conquests are great, but they haven’t brought him joy. Celebrating life’s moments and sharing experiences with people who matter most are what truly makes him happy.

Entrepreneurs have a vision that they’re trying to make a reality. Often, they think about little else—and sometimes that’s not a good thing. For example, one of my closest friends once invited me to join him and another college friend on a trip to South Africa. It was an opportunity to see a special part of the world with people I’m close to. But I was so focused on making CCAW a success that I thought I couldn’t afford to take the time off. To this day I regret that decision.

I agree with what my friend said. For all the success I had with CCAW, it’s the moments with friends and family that I cherish most. If you know what brings you joy, don’t routinely sacrifice it to your work. Faced with a decision like mine, make it carefully. The opportunity to go to South Africa with friends—or whatever version of such an opportunity turns up in your life—may never come again. Even ordinary chances to enjoy a meal, a concert—whatever floats your boat—with your family or friends are gold. Yes, if you’re an entrepreneur, you must work super hard. But don’t sacrifice your relationships. Make time for what matters most.

Yesterday I caught up with a good friend who’s also an entrepreneur. He said he was recently asked, “What would you change or do differently?” We’ve both been asked this question for various reasons, so we had a great chat about it.

Things will inevitably get challenging during the entrepreneurial journey. Entrepreneurs will find themselves making important decisions based on imperfect information. Having lived this scenario many times, we agreed about what matters most:

• Everything happens for a reason. The reason may not be clear at the time, but there is one. Take time to reflect on what happened, and why, so you can apply what you learn in the future. What seems like a failure today could be a steppingstone to a decision that leads to massive success. Reflection and the understanding it engenders are key to improving your decision-making.
• Neither of us would change any of our decisions. We don’t second-guess them. We didn’t know then what we know now, and we stand by our decisions because we did the best we could with the knowledge and other resources available to us. Don’t continually relive the past. Focus on the future.
• It isn’t over until the clock reads double zero. Stay focused on getting the win. Sometimes you’ll make decisions that don’t pan out. That’s OK. Dust yourself off and get back in the game. Remember that it isn’t over yet and you can still make a comeback. If you win in the end, all your turnovers and air balls don’t matter anymore.

My conversation with my buddy was a great reminder for both of us that we wouldn’t change a single thing. As he so eloquently put it, “All windshield, no rearview mirror over here!”

Yesterday, I wrote about the insights Eric Feng shared during the Outlander Speaking Series. One of the things that really resonated with me was his answer to a question. For context, I asked him, “What’s one thing you know now that you wish you had known as a first-time founder early in your career?” Here’s his response: closing windows of opportunity. This has been on my mind all day today.

At CCAW, as at every startup, we always had a ton of things we were working on. Looking back, Eric is so right. I wish I had consistently prioritized opportunities based on their closing windows. Early on, we had an opportunity to be one of the first to offer a specific product category for online purchase by consumers. The market for this category is huge and it was primed for disruption. Being first mover would have required our full attention and fighting some battles to change an antiquated space. There were lots of technical challenges and we lacked a thorough understanding of the category and key relationships in the space. Big hurdles, but they were surmountable and worth the effort because of the size of the opportunity.

I chose to instead continue to focus on a product category that wasn’t growing but in which we had established relationships. Fast forward a few years: we tried to play catch-up in the high-growth product category—but we never did catch up. A competitor beat us to the punch and became a household name. That was a $250-million-annual-revenue decision. I should have pounced on the closing window of opportunity to be a first mover. I didn’t, and we paid the price.

Eric’s concept is simple and spot-on. It applies to everyone, not just entrepreneurs. Here’s an example that everyone can relate to: relationships. No one is immortal, so every relationship is a closing window of opportunity. I wish I’d spent more time with certain people who were in my life when I was young but who’ve since passed.

My mother reminds me often of something my grandmother told her: “Give me my roses while I can still smell them and sense the enjoyment they bring me.” I think Eric and my grandmother are loosely saying the same thing: some opportunities won’t be around forever. Be mindful of which ones are important, prioritize them, and make the most of them while you can—in all aspects of life!

Recently I was sharing with a buddy best practices I used to manage CCAW. Technology systems. Team alignment frameworks. How I structured my day to juggle my multiple hats. And we talked about how my responsibilities expanded as the company grew. When I finished, he seemed dazed. “Sounds like a lot to deal with,” he said. “How do I get the point where I can handle all that at once?”

As I rattled off all the things I did, I realized it was a lot. The days were packed and the to-do list was never-ending. CCAW was a ship and I was the captain, responsible for it sailing smoothly. With so many moving pieces that kept increasing in complexity, it was no small task to manage it all.

I was always busy. There was never a time when I was like ”Hmmm . . . I don’t have enough stuff to do; I think I’ll go find more to add to my plate so I can keep busy.” As the company grew, we were confronted with new challenges that forced me to rise to the occasion. It was uncomfortable, and each hurdle forced me to take on a little more than I thought I could handle. After years of this, my capacity was many times larger. I was able to handle much more than I thought I was capable of when I started CCAW.

My journey as a founder was one of gradual growth—over years—that came about because I kept being put in uncomfortable situations that tested my limits.

If you’re looking to do something great but aren’t sure if you have what it takes, know this: most people who were once in your shoes didn’t have “it” in the beginning. They grew along the way, and you can too!

When I was in the corporate world, the path was clear. You show up and do good work and you’ll be promoted. I didn’t have to put much thought into it. It was known. Chatting with a friend today reminded me that I had to unlearn this and take a different approach as an entrepreneur.

My first few years at CCAW, I worked hard. That hard work was rewarded with (in my eyes) marginal progress, and I was nowhere near where I wanted to be. I couldn’t see a path to get there, either. I’d applied what I’d learned in corporate America, but it wasn’t working very well. Our revenue was growing, but I was struggling in many areas. It felt like I was on a hamster wheel spending more time working in the business than on it. I was stressed and working a ridiculous number of hours.

I eventually decided to take a step back. I realized that I was hoping things would just fall into place. It wasn’t working out like that. I spent time crystalizing where I wanted to be and pinpointing what was preventing me from getting there. I realized that to reach my destination in a healthy way, I would have to be much more intentional. I would need to rebuild our operational foundation and change our pricing strategy. I estimated that it would take a few months and that our revenue would decline during that period.

The process ending up taking a year and reduced revenue almost 30%, from $688,000 to $485,000. It was extremely painful and I was scared. I wasn’t sure that we’d survive this self-inflicted pain. Vendors were asking why we weren’t buying as much and we faced a cash crunch. Ultimately, though, it proved to be the right call. We built a stronger operational foundation and were positioned for growth. The next year, annual revenue was $793,000 and the following year it surpassed $1 million. We were rolling. I was still stressed, but I felt like I could work on the business more and continue to grow.

My takeaway from this experience was that intentionality is powerful. If I want something, I need to articulate it clearly (to myself and others), put in time and effort, and align my decisions with what I want to make happen. That means that sometimes I’ll have to endure short-term pain to reach my ultimate destination, but that’s OK. I have to be intentional about what I do in the present to reach a particular destination. I won’t just miraculously end up there.

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.