On Longevity

After twenty five years in tech and a decade as a start up executive, this is how I stay in the game.

I’m fortunate to spend time with a small group of people whom I consider to be the next generation of startup c-level executives. 

These folks have a lot in common. 

They’re often in VP level roles, have crazy high ceilings, and they’re perpetually looking to take their game to the next level.

They’re running hard. Really hard.

Oftentimes, they’re running just as hard at home.

Sometimes, they run until they crash.

In many cases this career apex seems to coincide with having a young family.

I’ve been there. 

I find this comes up a lot in our conversations. 

I find myself talking about maintenance.

Maintenance

You don’t drive your car until it fails. 

When you maintain your car it lasts longer and runs better.

I’m into maintenance.

Most people do this for their cars, but not for themselves or their career.

As a result, I’ve seen good people leave good companies simply because they’re tired.

In my personal journey, I can recall redlining early as a new executive in a growth business. 

My first instinct was to leave. 

The growth, the financial upside, the learning; none of it matters if you run to failure.

Upon reflection I realized that if I wanted to be a startup leader, I needed to learn how to thrive in that environment.

No matter where I go, here I am.

I needed maintenance.

I’m not here to tell you what to do, what worked for me may not work for you. The magic is in understanding the problem and then reaching your own solution.

Here are five maintenance concepts worth considering.

Calibrate Time and Priorities

In a startup, there is always more work to do than time to do it.

I remember thinking to myself one day that I could work twenty four hours a day on the business.

Workload always exceeds capacity.

In this construct two things become important.

The first is that you need to draw the line. It won’t be drawn for you.

You need to decide when to work and when not to work. 

There’s no punching in and punching out, you need to create those boundaries for yourself.

And, this determination should be made in the broader context of life, not career. You need time with family, friends, and kids. You need self care, whatever that means to you.

And you need time to think.

If work sucks up all the oxygen in your life, you won’t last and you won’t be effective.

Second, if we agree that workload exceeds capacity, then choosing what to work on becomes crucial.

If there are one hundred things to do and you have time for ten, then choosing the “right” ten is critical.

A lot of people never figure this out. 

But it’s one of the big differences between success and failure.

Here’s a simple exercise that I believe everyone should do from time to time.

Reflect on your work and life priorities and then spend a week recording how you spend your time.

Does your time allocation match your priorities?

In my experience usually it doesn’t.

There’s drift.

The exercise, performed periodically can help you recalibrate.

That’s maintenance.

Develop a Process

There are process problems and project problems.

Projects have clear beginnings and an end. They are event based.

Processes are ongoing, and usually the goal is optimization. 

Maintenance is a process problem.

If you’re in danger of burnout, that one vacation isn’t going to solve the problem.

Rather, I would consider building maintenance into your daily, weekly, monthly workflows. 

Here are a few examples from my personal life that I have found effective;

• Take one week off per quarter. That’s four opportunities per year to step off the treadmill and recalibrate

• Block beginning and end of each day. Mornings for reflection and afternoons to catch up on messages and transition to home life

• Exercise six days a week and Sundays off as a total reset

• Schedule 45 minute meetings. Leave 15 minutes between meetings to breathe, pee, reflect and prepare

• Try very hard to get 8 hours of sleep per night

• Eat right and limit alcohol. Understand the relationship between mood, energy and how I’m nourishing my body

• Think of weekends like mini vacations. Eliminate or compartmentalize work. Emergencies aside, weekends are critical to recharge. If I choose to work on a weekend, I try to carve out the time. That way I know I can spend the rest of the time recovering

Maintenance is a process not an event. Focus on what works for you and actively build it into your daily, weekly and monthly workflow. You will feel better, perform better and last longer.

Understand the Power of Identity

Something very powerful happened to me at some point in my career.

What I did became who I was.

I was Dan the CRO.

Identity is a powerful concept and can be a force for good and evil.

Attaching your identity to your job is not productive and can limit longevity.

We all know that startups are roller coasters. They’re high risk, volatile and dynamic.

If who you are is what you do, then your identity is going to ride that roller coaster. A professional failure becomes a failure of self.

That’s dangerous.

Here are a few concepts that have served me;

• Paul Graham advocates for keeping your identity small. His perspective is that people can't think clearly about anything that has become part of their identity. So the best plan is to let as few things into your identity as possible

• Brad Stulberg argues for diversification of identity. I may be Dan the CEO, but I am also Dan the father, athlete, writer, advisor and husband. Similar to a diversified stock portfolio, there’s risk in having all your emotional eggs in one basket

• Nassim Taleb advocates for identifying as a learner to become antifragile. In his view, this is a way to embrace inevitable disorder and stress. In other words, viewing setbacks as learning opportunities versus failures

• Warren Buffet recommends writing your own obituary and then figuring out how to live up to it. This adds perspective to your identity; do I want to be remembered as Dan the CEO or Dan the husband and father?

I borrow from all of this thinking as I have detangled what I do from who I am.

Identity maintenance creates resilience and helps me stay in the game.

Play the Infinite Game 

My first true startup experience began almost a decade ago and lasted five years.

I worked insanely hard.

I learned more in those five years than the previous fifteen.

We raised A, B, C rounds and had a significant exit.

I was promoted to a c-level executive.

By all accounts it was a successful run.

Unfortunately, I can only really appreciate the experience in hindsight. In the moment, there was a lot of suffering and very little recognition that I was part of something special. 

This taught me a valuable lesson about infinite games.

Simon Sinek describes the infinite game as an open-ended, long-term endeavour focused on continued participation and advancement, rather than a competition with a clear winner and loser. The goal is to perpetuate the game, not to win it outright.

This is true of business. 

This is true of life. 

If there’s no finish line, then you better enjoy the ride.

It’s about the happiness of pursuit not the pursuit of happiness. 

This is far easier said than done, but it begins with an acknowledgement of what game you're playing. 

If you understand the game, you can learn to play the game well.

Establish a Personal Board of Directors

Jason Lemkin describes startups as best suited for pirates and romantics; those who want to truly be owners, do crazy hard things and create things from nothing.

He’s right. 

But you don’t need to take on the world alone. 

Building a group around you to help brainstorm, solve problems or even just commiserate is so important. 

Most people intellectually understand this concept, but rarely do they spend an appropriate amount of time cultivating and engaging with their personal board of directors. 

Here are a few personal BoD recommendations;

• Informal or formal both work. A formal example could be a coach or peer group. Informal could be an old boss or a friend

• Look for diversity of thought, this will help round out your perspective when faced with challenges

• Keep the group small, think navy seals versus the navy. You want to be able to actively nurture these relationships

• Reciprocal is best. I have learned a great deal helping other people. Give as much as you take. Learn and teach

• Be transparent. There isn’t a lot of value if you can’t be yourself and be fully honest

• Maintain these relationships proactively, it's worth the investment

I cannot think of a time when I engaged someone on my personal board of directors and didn’t walk away feeling better. 

You may be a pirate and romantic but you’re not alone.

On Longevity

If it were easy, someone would already be doing it. 

In a startup challenges are inevitable, so doing your best means putting yourself in the best position for success. It’s not about surviving, it’s about thriving.

And if you want to last, you need maintenance. Here are five maintenance strategies that have worked for me;

• Align time and priorities. In startups workload exceeds capacity so you need to decide when you work and what you work on. This is a life decision, not a business decision.

• Develop a maintenance process to increase longevity. What are you doing daily, weekly and monthly to ensure you’re operating in easy mode? 

• Understand the power of identity. Exercise caution if what you do is who you are. Startups are volatile and high risk. Detach professional failures from failures of self.

• Play the infinite game. Understand that the game you're playing has no finish line. The goal is to keep playing and find joy in the pursuit. 

• Build a personal board of directors. Startups may be for pirates and romantics, but that doesn’t mean you have to face the world alone. Building a network around you will help commiserate and think through difficult problems.

Onward.