A few lessons from 10 years on the job

Concluding my first decade of work has offered a reason to pause and reflect. The me of 10 years ago wouldn't recognize much of who I am today -- hopefully that's for the better. There's a number of studies that suggest our biological growth, specifically our brain maturity, is still critically developing until the age of 26, or 28, or even 30+. This was certainly true for me and I had a mountain of influence along the way.

I've been fortunate to work with extraordinary peers, leaders, and mentors. People that taught me about business and also about the world. And while I've had countless 1:1s, coffee chats, and life advice from great people I trust -- many of the lessons I've learned actually came from observation. This is where "fortune" matters. I have been lucky enough to be in environments where I could simply observe thoughtful people impart sage wisdom -- and subconsciously evolve. I am forever thankful for those opportunities.

While there have been many lessons in sales, management, motivation, execution, strategy, performance and so on -- these are just a few things I've picked up that have served me well and helped me grow professionally. Call it a letter to my younger self but needless to say I would have benefited from learning a few of these things earlier on.

Never be scared to ask for help. I used to worry that asking for help would make me look weak. You know what actually looks weak? Doing it alone and making bad decisions or falling flat. Ask for guidance. Humans love to be valuable and you’ll kick more ass thanks to their help.

If you sense it, say it. We're often afraid to acknowledge suspect body language or negative energy. If something feels off then speak up. Harm will rarely follow and it will more likely foster a stronger relationship, especially in sales. This includes self observation and admitting when you're wrong.

You are the average of the 5 people closest to you. Or maybe 3 or 10. But osmosis is real and those around you will dramatically impact the person you are whether you realize it or not. Choose wisely.

The biggest decisions of your career will happen when you’re not in the room. Understand the spheres of influence, demonstrate the skills required, and don't be naive. The network effect on your career is incredibly powerful. (See the first one)

If you want to progress in your career then do these three things exceptionally well: 1) crush the role you’re in 2) make those around you better 3) make your manager better. While the plan is simple in theory, it's far more challenging in execution.

Saying yes to something means you’re saying no to something else. We live in such a yes culture where we value taking on every new opportunity. Just remember there are always tradeoffs, both personally and professionally, so measure every alternative and pick your spots.

Complaining rarely gets you anywhere. And is often a detractor. Be aware of your perception and remove emotion from the equation. You can likely deliver the same message in an alternatively thoughtful and more meaningful way.

You, and only you, are in charge of your career. Big picture: we all need opportunities and I fully recognize the unjust privilege I've received as a white male. But I caution those that hold others accountable for their success. It's always on you.

When asked a question always answer with: the yes/no first, follow with an example, and leave any necessary commentary for the end.

Measuring the ROI of my personal time has been incredibly insightful. I'm not suggesting you ruthlessly measure friend groups 1 versus 2 when making dinner plans -- but can you measure the ROI of scrolling through Instagram? What is it? It might be best to invest elsewhere. My ongoing challenge from here is analysis paralysis. (See the next one)

If you have aspirations, start NOW. Like, right now. If you don't take the first step, even the most mediocre and unimpressive one, you'll be right in the same spot a year from now. I've spent the last couple years wanting to write more. This is my first step.

Cliches are cliche for a reason. Just think about it. 

Sobriety has been the most underrated and undervalued way to increase my happiness. This one has been tough. Cultural norms and social conformity control us. And drinking socially is also just fun. But in my extended periods of sobriety I feel superhuman. It's really nice.

Reinvesting time and money into diet, exercise, health and wellness is one of the best decision I’ve made. This isn't rocket science but it's the truth. My latest additions: cryotherapy, massages, guided stretching, and meditation = 1 round of drinks. (See the previous one)

Drink more water than you think you need -- or want. It's good for you.

It’s okay to laugh at yourself. Self deprecation can be healthy. This journey isn't easy and fraught with unwanted stress, anxiety, and self-inflicted worry. Life is too short to take yourself too seriously.

Take every last hour of your PTO — and don't feel guilty. Workplace vacation shaming is bullshit. Don't stand for it. And to that end, travel early and often. There is no better way to gain perspective, find fulfillment, and learn about yourself then seeing the world.

I'm looking forward to many more lessons over the next 10 years. What are some of the things you've picked up along the way?

Many thanks to those (both directly and indirectly) who have influenced my professional growth: Holly Procter, Peter Kim, John Richards, Steve Sanders, Justin Geller, Duncan Carvey, Tenny Wan, Mike Derezin, Mike Gamson, Jeff Weiner