What If This Were My Last Newsletter?

Last week, Robert Rose and I recorded a special episode of This Old Marketing: What if this were our last episode ever?

Don’t worry. We’re not ending the podcast. But after more than 550 episodes together, we thought it would be interesting to talk about the things we’ve always wanted to say but never had the opportunity to say. Things we got wrong. Things we believe but rarely discuss. Things that might have nothing to do with marketing at all.

It turned into one of the more interesting conversations we’ve had in 13 years.

Afterward, I started thinking about this newsletter. What if this were the last email I ever sent you? After all these years of writing about marketing, business, content creation, and life, what would I want to leave you with?

I’ve been fortunate enough to accomplish a few things in my career. I’ve also made an extraordinary number of mistakes. Looking back, I think the mistakes taught me considerably more than the successes.

So here goes. Five things I’d want you to know.

1. Be Less Certain

I believe one of the most dangerous things a person can be is absolutely certain.

When we’re convinced we’re right about something, we stop asking questions. We stop listening. We start looking for information that confirms our beliefs and ignoring anything that challenges them. I’ve been guilty of this more times than I’d like to admit.

Whether we’re talking about business, politics, religion, or relationships, I think we’d all benefit from being a little less certain.

Here’s a test I like. Can you explain the other side’s argument in a way that the other side would agree with? If you can’t, maybe you don’t know enough to have such a strong opinion.

I’m not suggesting we shouldn’t have convictions. But leave a little room for the possibility that you’re wrong. That small amount of uncertainty keeps you curious, keeps you learning, and sometimes keeps you from doing something incredibly stupid.

2. Make Your Job Your Side Hustle

I’ve come to believe that most of us have our relationship with work backward.

We spend our lives building careers, climbing ladders, chasing promotions, and making our jobs the central part of our identities. Meanwhile, the things we really want to do get pushed into the evenings, weekends, or some imaginary future when we’ll finally have enough time.

What if we reversed that?

If you work for someone else, think about your job as the thing that finances your real mission. The thing you want to build. The people you want to help. The difference you want to make in the world.

You don’t have to quit your job. You might even love your job. But don’t let employment become the only thing you’re working toward.

And while we’re talking about work, here’s something else I’ve learned.

The real purpose of making money is to be able to say no.

No to the client you don’t want. No to the project that doesn’t matter. No to the opportunity that takes you away from the people you love. Money provides options. Options provide freedom. And freedom gives you the ability to build a life on your terms.

The trick is figuring out what enough looks like. Otherwise, you’ll spend your entire life chasing more without ever knowing why.

3. Take Yourself Out of the Game

In 2018, after selling Content Marketing Institute, ​I took a full-year sabbatical​.

No business travel. No conferences. No social media. I even went completely electronics-free for 30 days.

I read books. I wrote fiction. I ran. I made lunches for my kids. I worked around the house and spent time with people I loved. It was one of the most important years of my life.

For years, I’d been caught up in the daily grind of building something. Meetings. Emails. Deadlines. More meetings. There was always something urgent that needed my attention.

When I stepped away, I realized how difficult it had been to see what actually mattered while I was constantly doing things.

I think everyone needs a sabbatical of some kind. It doesn’t have to be a year. It might be a month or a week (or at least, maybe a weekend?). But you need enough distance from your normal routine to ask some important questions.

Am I doing what I want to be doing? Am I spending time with the right people? If I keep going exactly as I am, is this where I want to end up?

You might be surprised by the answers.

4. Relationships Are the Point

As I get older, this one becomes increasingly important.

I think most of us understand that relationships make life worth living. But knowing that and actually doing something about it are very different things.

I have two adult children. With my oldest, we make time for roller coaster trips. With my youngest, it’s baseball and sports trips. These are some of my favorite experiences in the world.

But here’s the thing. They don’t happen by accident. We have to plan them. We have to put them on the calendar. We have to make them important enough that other things don’t get in the way.

I want to have amazing relationships with my children when they’re 30, 40, 50, and beyond. I can’t just hope that happens. I have to do something today to make those relationships stronger tomorrow.

The same goes for friendships. We need people who support us, challenge us, and tell us when we’re full of it.

Think about the people you want in your life 20 years from now. Are you investing in those relationships today?

5. Movement Creates Opportunity

Recently, I spoke to a group of students at the University of San Diego.

During the presentation, I showed a slide with some of my career accomplishments. Starting companies. Creating Content Marketing World. Selling a business. Writing books.

Then I showed another slide. The other version of my career. The mistakes, the failures, the strange decisions, the things that made absolutely no sense at the time.

And I realized something. Almost nothing important in my career happened because I had some brilliant master plan. It happened because we were constantly doing things.

We tried ideas. We attended events. We met people. We started projects. We made decisions without knowing where they would lead.

Some things worked. Many didn’t. But each action created another possibility.

Movement creates energy. Energy creates opportunities.

I think far too many people spend their lives waiting. Waiting for the right time. Waiting until they have enough money. Waiting until they’re ready. Waiting for somebody to give them permission.

My advice is to stop waiting. Go to the event. Meet the person. Start the project. Write the book. Have the uncomfortable conversation. Do something that scares you a little.

You have no idea what might happen because you did.

One Last Thing

It’s funny how this all fits together.

Be less certain. Build a life where you have choices. Step away occasionally to see what matters. Invest in the people you love. And through all of it, keep moving.

If there’s a common thread, it’s that life doesn’t just happen to us. We have far more control over our choices than we sometimes realize.

I started this exercise wondering what I’d say if this were my last newsletter. And it brought me back to a question Robert and I discussed on the podcast.

After everything we’ve accomplished, what do we now believe matters that we didn’t understand 20 years ago?

For me, it’s not the accomplishments themselves. It’s having the freedom to choose what comes next, the people to share it with, and the willingness to keep trying things even when I don’t know how they’ll turn out.

Thankfully, this isn’t my last newsletter. There’s still a lot I want to do.

P.S.: Ready to take a chance on yourself?

If you’ve been putting off that idea, project, or big move, maybe it’s time to stop waiting. My free 21-Day Challenge is designed to help you stop overthinking and start taking action. One small step every day for 21 days.

​Take the 21-Day Challenge​