I was sitting in the hospital, waiting for my wife to go into labor with our firstborn child, when I received a text that got my wheels turning...
"What is it that you want?"
I honestly had no idea how to answer.
I had just released a new and improved portfolio of my work, and I was really proud of it. The design was sleek. The content was useful. I created a "choose your own adventure"-style page that could be navigated by company and skill-set. It was neat and I was proud.
But all of that detail couldn't answer this one, simple question. What is it that I actually want?
I punted and decided to come back to the question after I got some sleep.
A week and a half later, I haven't gotten much sleep (thank you, newborn son), but I've given this question a lot of thought. The thing I can't get out of my head is my relationship with my father and how it's evolved over the past decade. Especially in the past few years, he and I have become more like friends than father-and-son, and I've relished having the opportunity to talk to him about his life and career.
As I look at my son, I imagine sitting at a bar with him 25 years from now, having a beer, and talking through his career journey. In that moment, he's probably going to ask me a lot of questions about how I made decisions in my 20s and 30s, like I did with my dad.
When that moment comes, I want to have some good answers, and candidly, I don't think I would be proud of the answers I'd give so far in my career.
So, here's what I want to tell my son 25 years from now...
To date, I've used one simple heuristic to decide what job is right for me... How big is the challenge? The bigger the challenge, the better the opportunity. That led me to take on roles that were pioneering. I've never had a proper onboarding or taken a job that someone had before me. I've spent my career blazing trails and learning-by-doing.
It was a fantastic catalyst for growth, but not for happiness and fulfillment.
There have been moments in my career where I've felt like a contortionist, bending my own backbone to support cultural norms that I didn't fully embrace. Today, I sit at a crossroads where I can make a different choice. I can state my core values and refuse any role that doesn't fit them, instead of the other way around.
So, what values are truly foundational to me? What heuristic will I be proud to explain to my son 25 years from now on a patio, drinking a beer?
I found four...
"The best companies aren't families. They're supporters of families. Allies of families. They're there to provide healthy, fulfilling work environments so that when workers shut their laptops at a reasonable hour, they're the best husbands, wives, parents, siblings, and children they can be." - Jason Fried
Show me your calendar and I'll show you your priorities.
Early in my career, I let late-night work events and weekend projects take priority. Today, I'm in a different place in life and that's no longer a tenable option.
Instead, my work will happen in accordance with my family life. I will build my schedule around my family's needs, not the other way around. That may mean, for example, working from 6 AM to 3 PM. It will certainly mean saying "no" to a lot of meetings. Efficiency and effectiveness are essential, because I don't have time to waste.
I will also set clear boundaries between my work and home lives. I'll provide a clear communication waterfall so we're aligned on expectations. This will ensure that I'm available when you need me, while also guarding my time with my family from unnecessary interruption.
Finally, we will communicate often about my mental and emotional health. If my role, organization, and manager are making my anxiety and depression worse, I will provide ample coaching to correct the issue. That said, my expectation is that behaviors will change based on this coaching. I need to be mentally healthy to be present for my family, and no job is worth that sacrifice.
"When you're creating something out of nothing, the first rule is to agree." - Tina Fey
I spent a good portion of my life doing sketch, standup, and improv comedy. I had the privilege of collaborating with dozens of artists who are far more talented than myself, and I've learned some really valuable lessons about doing great work.
"Yes, and" is the most fundamental rule of improv, but it transcends comedy. It's a rule that makes us all better teammates and collaborators.
To demonstrate this principle, let's imagine that you and I are working together. You really want to launch some video content on our blog, and I'm skeptical that the benefit will outweigh the cost. A poor approach might look like this:
You: I think we should launch some videos.
Me: I don't know, it feels too costly to me. Maybe we could try something small, but I don't want to invest in it until next quarter.
If you were in that situation, how likely would you be to come to me with an idea in the future? Not likely. What if, instead, the interaction went like this?
You: I think we should launch some videos.
Me: I love the idea of testing video out! I bet we could launch some low-cost, low-fidelity videos in the next two weeks to test the concept out. If we see results, we might be able to find some real budget to put behind it next quarter.
Think of the impact that reaction has. I've just rewarded you with dopamine and instant gratification for coming up with an idea, and I've built upon it in a way that addresses some of my concerns. You are being rewarded for coming up with a new idea and bringing it to me. In the first example, you're being punished for that same instinct, even though the outcome of both reactions are identical.
Another useful model for this is the "Appreciative Inquiry" framework.
Bottom line: If you don't embrace this type of collaboration, we won't work well together.
"What if instead of trying to be amazing you just focused on being useful?" - Jay Baer
One of the greatest challenges I face in my career is the amorphous definition of marketing. Depending on your business goals, great marketing can mean one of 10,000 different things, and many business leaders aren't clear on what marketing strategy is going to be right for their organization.
If you're interested in working with me, let me save you some time and tell you what I specialize in.
I specialize in driving inbound demand with content and email marketing. I believe that, in the long-run, this is the most effective way to grow a business.
Zig Ziglar used to say "You can have everything in life you want, if you will just help other people get what they want." I fundamentally do not believe that the best way to help other people get what they want is by cold calling or cold emailing them. I think a far more effective tact is to provide immense value to folks first and learn what pains they will pay you to solve for them over time. My process is simple and effective:
This approach is far more profitable and repeatable than paid ads and other outbound marketing tactics. Not only does it generate better ROI, but it creates an audience, content, and data that you own. That means that you don't need to pay the high rents that Google, Facebook, and LinkedIn charge for their audience and data. You can also use these assets to make the system more effective over time. This is what I build.
The catch is that it takes time. This will not deliver dozens of qualified meetings this month, but it will pay dividends 3, 6, 9, and 12 months from now. If you don't have that level of patience, don't work with me.
"Are you going to continue to burn more money than you earn, hoping that one day profit will finally materialize? Or are you going to choose to give endless growth a rest until the numbers work?" - David Heinemeier Hansson
I believe that it doesn't have to be crazy at work.
There are times in every organization where things go a little nuts... Maybe there's a big industry shake-up, or maybe your sales cycle is seasonal so you have a busy period. This is normal. Some craziness is acceptable.
But if things are routinely "crazy" at work, that's a clear sign of mismanagement.
Sometimes, that means your people managers are bad. Other times, it means that your business model is untenable and artificially propped up by VC dollars. It may be a sign that you have a toxic work culture that no level of sugar coating can fully cover.
Regardless, I'm choosing not to pursue crazy work or crazy growth. I've lived that life and hit those goals. I've also seen what happens when businesses make a different choice. The opportunity cost of crazy, rapid, hockey stick growth is calm, predictable, sustainable growth. That's way sexier to me.
If I'm going to do the best work of my career, I need to feel psychologically safe. It's really, really hard to feel that way when it's always crazy at work. I'm going to choose to partner with business leaders who have the courage to turn down the Faustian bargain of rapid growth at all costs and instead reward those who prioritize a longer-term view of their business.
I want to build a career that abides by those four simple principles. I want to partner with organizations that take my core values seriously. I want to stand by these ideals, even when it's disadvantageous to my career and earning potential.
If you want to join me on this journey, I'd love to meet you.