What I Learned in 2024

There’s a new saying that I’ve come to love: You Win or You Learn.

In 2024, I did a little of both. I started my own business in late February 2024 at the age of 49 ½. As I attended 50th birthday parties of my friends throughout the year, the most common discussion point was how many years they had until retirement. 

In the midst of year one of my new venture, these passing comments sparked a mix of thoughts for me.

During my best moments, I chuckled. “Retirement? Are you kidding? I’m so pumped for this new start!” 

In other moments, I thought, “What the hell am I thinking getting started with a new business at 50?” 

It was a massive year of learning for me - perhaps the biggest learning year yet. Here are the top 5 lessons I learned in 2024.

LESSON ONE: New is gonna bring some hard with it

When I started, I refused to buy into the conventional wisdom that starting a new business had to be hard. I wasn’t being cocky. I just think that sometimes we talk ourselves into things being harder than they have to be.   

When I got my first client 45 days in, my instinct was reinforced. 

But just because I had that taste of early success, I didn’t account for unknown challenges that hit me later in the year.

For the past 22 years, I had been part of two teams - one at a school (Pingry), and one at a business (Tenna). In those 22 years, I was blessed to meet a lot of great people, make a lot of great friends, and be a part of a lot of great teams. 

It’s incredible to have the freedom of your own business. But one of the lessons I learned was that at times, it can be hard as a team of one.

I DEFINITELY learned that doing something new will bring some element of hard with it!

LESSON TWO: Timing is everything

2024 also reinforced the lesson that timing is everything. With the benefit of hindsight, I recognize that part of the reason I was able to land my first client was incredible timing.

I was fortunate to meet the leadership team just a few weeks after starting my business.

I also happened to meet them just at the moment when they were considering options and resources were in place to accelerate their growth. 

Even better, building a sales development team was at the top of the list of levers to accelerate.

If I had met them six months earlier, the timing would have been too early.

If I had met them three months later, it likely would have been too late to work together.  

Now that I’m in receipt of this lesson, it also has helped me realize a few other things...

When people don’t respond, it’s often because the timing isn’t right. It has nothing to do with the quality of your service, your pricing, your tenure, your expertise, or any other explanation we concoct in our minds. 

It’s just wrong timing.

So the next logical question is…how do you know it’s the right time?

Taking the time to do my homework and learn more about my market helped me narrow my focus and understand more about which companies may be more receptive to a conversation. But the truth is, unless you’re on the inside, you’ll never really know the full picture. 

Which leaves me with this conclusion: 

The only way to make sure timing is on your side is to stay connected.

Despite the fact that most people won’t return your outreach via emails, calls, or LinkedIn messages, if you continue to to reach out, you will find your way into the “right time” a lot more often than if you settle for a passive approach.

LESSON THREE: Hang on loosely

Back when I was single in my 20s, I used to go on a lot of dates.

To clarify, I went on a lot of first dates - not too many second dates!

There were plenty of times I went on a date and wasn’t feeling it. But there were also plenty of first dates where I left with a ton of optimism about my future with that new someone.

So what did I do? I began to project the future.

I thought about the second date…the third date…the fourth date. Meeting my family. Future fun experiences I could share with this person. 

What usually happened?

Most of the time, there was no second date. And every time it happened, I was surprised, frustrated, and somewhat pessimistic about my prospects that I would ever find the right person.

Later in my 20s, I figured out a little more about who I was and what my calling was: teaching.  

Somehow, dating got easier. I didn’t focus as much on any individual date, and I began meeting more and more interesting people. Eventually at 29 I met the woman who would become my wife.

This year, I learned that lesson once again with my new business.

Initially, after every meeting, I would get really excited and fall in love with the opportunity. This is just my nature -  I get excited about the chance to help people and add value. 

But I also fell into the trap of getting really attached to each situation. In my mind, I pre-determined not only that the business would be won, but when and how it would be won. 

Naturally, when things didn’t go precisely according to my master plan of when and how everything was supposed to unfold, I got frustrated.

In August, a friend of mine, Brian Hemming, reminded me of a great way to look at opportunities in life. He shared wisdom from the old classic by 38 Special:

“Just hold on loosely

But don't let go

If you cling too tightly

You're gonna lose control “ 

This metaphor served me really well in the second half of 2024. 

It didn’t mean I cared about my business any less. Nor did it mean that I prepared any less for specific opportunities. It also didn’t mean that I would be any less present or focused when I got the chance to meet people. 

It simply meant that I exercised the discipline not to attach too much importance to any outcome.

I had to accept that I would do my best, and ultimately, I had to release myself to the reality of life that at age 50, I’m starting to accept: I can’t control everything. 

LESSON FOUR: You can’t do it alone

Building on lesson number one, I had some lonely times during 2024. When I look back at my life and think about how I operate when times get tough, my SOP is to go within. 

I challenge myself to carry the heavier burden, grind through whatever is in front of me, and keep my struggles to myself so that I can spare others from pain. I historically try not to talk about my own issues and challenges because I don’t want to bring others down, and I figure the less I speak of it and just bury it, I can overcome it.

This has served me well at certain times in my life. But I also realize that choosing this path has led to more isolation, prolonged problems, and ultimately, has slowed the ability to overcome some of my obstacles. 

By the end of 2024, I made a number of new friends who were also solopreneurs. This didn’t erase all the challenges, but it helped me understand that I wasn’t unique. I got great insights from guys who had more experience than me. I also had the chance to share my lessons with others who were just starting out and could benefit from my three months, six months, and eventually, nine months of wisdom.

2024 has highlighted my foolishness - once again - of trying to do it all myself. I’ve come to recognize the do-it-all-yourself approach is short-sighted, impractical, and even ego-driven.

I was reminded once again that if you want to do something you’ve never done before, you’re going to need all the help you can get in as many forms as possible. 

Once I accepted this truth, it became less about IF I should get help…but about WHO, WHEN, WHERE, and HOW I should ask for help. 

I am so grateful for all those who helped me - and will continue to help me - including new and old friends, family, former colleagues, and God above.

LESSON FIVE: Show Up

Technology connects us in ways that were unthinkable 30 years ago. From emails to texts to social media to virtual meetings, all these new modes are incredible ways to communicate.

When COVID hit in 2020, we adapted to a world in which we could operate virtually. This brought incredible benefits: increased efficiency by avoiding commuting time, widening our talent pool beyond the geographic limitations of an office setting, and enhanced potential work-life balance.

In time, there were also a few notable consequences. The top of the list? Lack of connection.

The lesson is not a battle cry for a nationwide five-day-a-week return to office. It is just a recognition that when you show up, things happen that can’t be done virtually.

Looking someone in the eye in person is different than looking someone in the eye on screen.

Congratulating someone in person with a face-to-face chat and a handshake is different than clicking the clap button in a virtual meeting. 

Sending someone a Slack or Teams message to bounce an idea off them is different from going to their desk and having a sixty-second back-and-forth conversation.

Finally, building a relationship with someone new through a Zoom meeting is quite different from sharing a meal at a conference or coming to a company HQ to see and feel what the person and team culture is really like.

When I made the choice to show up in 2024, I met more interesting new people, I forged deeper relationships, and I learned more from pushing through the discomfort of being there than I would have if I chose to stay at home.

As 2025 gets underway, I am committing to figuring out more opportunities where I can show up. I know that when I do, better things tend to happen.

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I’m so grateful for these lessons of 2024. 

As I wrote this piece, on some level, I recognize that I should “know” these lessons already! After all, none of them are rocket science. All of these are common sense insights.

That said, I also realize that common sense doesn’t always make for common practice.

Twelve months from now, I’m looking forward to the true test of these lessons - how well I continue to apply them. I sincerely hope that when 2026 rolls around, I will have listened to my own advice by have put these lessons into practice for all of 2025.

If I do, in 2026, I should have a fresh set of new insights to build on!

#lessons