Life Lessons from a 50 Year Old

Summary

Ten things my younger self probably wouldn't listen to, and the inspirations in my life responsible for much of it. The list ranges from starting a business without waiting for the right moment to treating rest as a discipline instead of a reward, with a candid section on managing anxiety and naming courage failures for what they are. It's a personal, unvarnished set of lessons from 18 years running Heinz Marketing, more about how to decide and show up than what to produce.

This is a picture of Beth and me on the wall of my basement office, from back when I was a lot skinnier and a lot younger.

I turn 50 today (or more accurately, as my mom reminds me annually, tonight).

Every lesson below would have been useless to that guy. Somebody almost certainly told him most of them already back then. He’d have nodded, thought “sure, makes sense,” and then gone and learned every one of them the expensive way regardless, which as far as I can tell is the only way any of it goes in and sticks.

I’m writing it anyway because 50 years in, including almost 18 running Heinz Marketing, these are ten things I’ve accepted as truth.

1. Don’t wait for the right moment.

I started Heinz Marketing on November 24th, 2008, with a laptop and a bus pass. Literally, that was it. The stock market had tanked a few weeks earlier. Beth was pregnant with our first child. So naturally that was the moment I quit my job and my benefits and went out on my own. Smart right?!

I didn’t design it that way, nobody in their sane mind would. I’ve said for years, if I had waited for the right moment to get married, to have kids or to start a business, I would still be waiting.

The right moment is a story we tell ourselves so that waiting feels like strategy. It isn’t. Some of what worked out for me was luck and some of it was not knowing enough to be scared, and I’m not going to pretend otherwise. What I had instead of good timing was Beth, who in those early days had more confidence in me than I had in myself.

I have never once heard somebody my age say they wish they’d waited longer.

2. The job outlasts the tools.

My dad ran marketing and sales for a Caterpillar Tractor territory in Northern California and Hawaii (rough gig right?!) for 30 years. I asked him once how he did his job without a computer. I genuinely couldn’t picture it. He said the work was the same, the tools were just different. Memos instead of emails, red pencils instead of rev marks.

So much about how my dad worked is now obsolete. The tools, media mix, channels, even org chart and especially the pace. Nothing about what he was actually doing is obsolete at all. He was figuring out target accounts, where there was interest and intent, why they needed it, who else had to sign off and how to be the person they trusted when the decision finally came. That job is still the job.

So when people ask me whether AI is going to end marketing, I think about my dad with no computer, doing my job.

The methods are always temporary. The work and objective underneath them is not.

3. Show up.

We’ve done more than 370 episodes of Sales Pipeline Radio. I’ve spent 30 minutes with Brent Adamson almost every Friday morning for close to three years. CMO Coffee Talk runs every Friday morning, twice, like clockwork.

There’s no genius in any of that. It’s on the calendar. We book good topics/guests and we make it happen.

Plenty of those episodes were mediocre and a few were genuinely bad. That’s the part people miss when they wait to have something worth saying. You cannot tell in advance which one matters. The only way to find the ones that count is to keep the appointment on the days you don’t feel like it, which is most of them.

People overrate the plan and underrate the appointment. Whatever you’re trying to build, stop renegotiating with yourself every week about whether today is the day. Today is the day. So is tomorrow and so on.

And can I tell you a secret? Sometimes I have a meeting booked and want to chicken out of it at the last minute. Whether I’m tired or anxious or worried I won’t “say the right thing” it can feel like not doing the meeting is the easy way out. And every single time I’m much happier I kept it.

Show up.

4. Judge how people decide, not what they produce.

We’ve hired a lot of marketers over the years and gotten it wrong plenty of times. Every miss I can remember came from evaluating what someone had produced instead of how they decided what to produce. I over-indexed on their past instead of their capacity and potential.

A resume is a list of outputs. So is a LinkedIn profile, and so is most of how we size each other up at work. Outputs tell you what the conditions allowed. They tell you very little about the person, because a good decision in a bad situation often produces a worse-looking result than a lazy decision in a great one.

Ask people what they chose and why. Ask what they’d do differently. The ones who can walk you through their reasoning, including the parts that didn’t work, are the ones worth betting on.

The same test works on yourself, and it’s less flattering. I can point to results I got that I don’t deserve much credit for. I can also point to a couple of calls I’m proud of that didn’t work at all.

5. Put yourself first.

I wrote a version of this on the ten year anniversary of Heinz Marketing, and I believe it more now than I did then.

Putting yourself first is not selfish. By defining and prioritizing what I need for myself, I free up more of my time and energy to serve everyone else. Time spent serving other people becomes time you relish instead of time you resent, and the difference between those two is almost entirely whether you got what you needed first.

Write down what actually matters to you, as specifically as you can, then say it out loud to your spouse, mentor and/or manager. Most of us assume our needs are going to be an imposition. They’re usually much easier to accommodate than we think, and the resentment we’re protecting everyone from will eventually do damage.

I’ve violated this more times than I’ve honored it. I’m still better at prescribing it than doing it. It’s still the right thing to do.

At work, as a leader, I want to do right by our employees and clients. Sometimes that manifests as wanting to take the load off of people and do more of the work myself.

In reality, that can come across as micromanaging or not letting people do THEIR job. Don’t assume or infer, have the direct conversation. Everyone will be happier as a result.

6. Rest is a discipline, not a reward.

Every year after school gets out my family goes to Encinitas, California for two weeks and I don’t touch a laptop. Our team knows I’m dead serious about PTO. You’ve earned that time and we don’t want to hear from you.

Ten years ago the backlog waiting for me would have eaten my first three days and most of my good mood. Last year I was down to about 35 emails by noon on my first day back. The difference wasn’t discipline on vacation. I was as checked out as ever, and that’s the whole point.

The difference was the system around it. Get your real dependencies done before you go, not your inbox. Delegate by naming the thing and naming the person, not by asking someone to keep an eye on things. Write an out of office that actually closes the loop instead of promising you’ll check in periodically, because then you’ve signed up to check in periodically and you’ll resent it by day three. Block your first day back before you leave, before somebody else fills it with a 9am meeting.

And when you get back you’re going to be wiped out by mid-afternoon of that first day. That’s not a sign you’re behind. It means you actually rested, which was the whole idea.

Guilt-free time off is an engineering problem. Whether it’s a long vacation or weekend or just a Thursday night, take the time.

7. Your anxiety is a lying asshole.

Beth still reminds me of this regularly.

When the stakes feel high and my brain decides the worst version of future events is already happening, despite some good therapy and meds, anxiety still gets to me. It’s a disease of control, after all, and there’s literally no such thing as control. It’s that irrational gap we keep fighting against.

I wrote about this publicly for the first time only recently, at 49. I share it here because I know I’m not alone, and because we all have our demons, and because a few things I learned the hard way might help somebody else:

Say it to a person. Not into a journal and not into your own head. Out loud, to your partner or a friend or a professional. A book or a podcast (or partner) can help, but nothing shrinks the thing faster than hearing yourself describe it to someone who’s listening.

Move your body when the spiral starts. I swear it works, and the more you make it a habit the faster your brain and body will recognize and respond to it.

Name the actual worst case out loud. This can be scary but it also works. Say the specific thing you’re afraid of, in words, and then say what you would do if it happened. The answers don’t solve it, but they make it smaller. Every time.

8. Most failures are courage failures.

Most of the failures I see (and experience) aren’t process failures. They’re courage failures. I’ve failed this test So. Many. Times.

The conversation I didn’t have (at home and the office). The hire I knew wasn’t working eight months before I did anything about it. The client I should have fired. The pricing I should have raised but was worried about rejection.

The thing we know in our gut in the meeting and don’t say because there are eleven people on the call and it’s scary as hell to speak up.

We think another framework or book or process is going to fix this when what’s missing is nerve. It’s more comfortable to redesign the process than to admit the process was never the problem, and a new framework buys you another quarter of looking busy while the actual decision still sits there unaddressed.

These are choices. Almost all of them are reversible, written in pencil, which should make you braver rather than more careful. Don’t let someone else make the expensive decisions for you.

9. Help people feel confident in themselves.

Brent Adamson came to my house a couple of months ago and within 15 minutes he was building paper airplanes with my son. If you don’t know Brent beyond his brilliant content, that’s the guy in a nutshell.

He introduced me (and the world through his book The Framemaking Sale) to the idea that the best thing you can do for another person, whether that’s a buyer or a colleague or your own child, is help them feel confident in themselves. It sounds almost trivial but it reorganizes everything.

Most of us have it backwards, and I did for a long time. We want to be the smartest voice in the room, the one with the answer, the one they call. That instinct feels like generosity and it’s actually a way of keeping people slightly dependent on us. The alternative is harder and quieter. You ask the question that helps them get there themselves.

It has changed how I sell. It has changed how I parent, which I did not see coming. It’s changed how I show up as a friend, as well as what I understand about leadership at this point.

10. Be the whole person in the frame.

A while back I recorded another virtual event presentation from my basement office. My kids were running around upstairs and I could hear them the whole time, and I remember wondering how it was possible for them to be that loud!

Behind me was my piano, some baseball bats off to the side, my daughter’s art on the wall and a couple haphazard stacks of books. Not clean but real.

We are not robots. We are not purely professionals. We are full human beings, and the version of you with the branded backdrop might just make you appear less authentic.

This goes both directions. Something I do in a lot of conversations now is ask a specific question twice. Somebody says they’re fine, and then I ask again. “Okay. No. Really, no. How are you doing?” To get the real answer. It’s uncomfortable for about four seconds and then it isn’t.

Somebody told me recently they didn’t know if the treadmill could run any faster, that it felt like max speed. That’s not a thing you find out from the first question. And people really do want to answer the second if you give them permission, space and grace.

That skinnier and younger guy on the wall with his future wife? I wouldn’t tell him any of this. He wouldn’t have believed most of it, and he needed to get it wrong himself, which is probably the eleventh lesson and the one I’m trying to lean into with my kids now.

Come find me at 60 and I’ll tell you which of these ten I got wrong and what I’ve learned since.

This post originally appeared on Matt Heinz’s Substack.