10 Principles for a Fulfilling, Fun, and Successful Career

This blog is for the soon-to-be/recent grads and early career folks.?

Many students, recent grads, and early career folks reach out to me on LinkedIn for career advice. Because I can't possibly sync or write back to everyone, I thought it would be useful to write a blog about some of the principles I have found helpful in finding growth, meaning, and fun so far in my career.?

As AI creeps into taking on many of the hard skills we have held so dear in tech, what's left, I think, is to understand what machines can’t do i.e. what soft skills or “principles” you can focus on to distinguish yourself.

I hope publishing this helps a few of you along the way. Feel free to share this with whoever it can help, and if you have any principles to add that have helped you, I would love to hear them.?

1. Know and grow your superpowers?

Along the way, you'll hear a ton of advice about finding your weaknesses and growing them, and yes, that's important, especially for growth-minded people. However, much of that growth will happen naturally, and while you shouldn't be blind to where you are weak and should always embrace feedback in every form (it really is a gift), I have found that figuring out where you truly excel and are differentiated early is a game changer.

It took me far too long in my career to realize this principle, so I put it first. There are many ways you can try to find your strengths, such as through different personality tests or strengths finder (highly recommended). But overall, the best way is to listen to the people around you—your teachers, friends, bosses, etc. I have found that my greatest strengths are the things that come naturally that I thought, "Oh, that's not a superpower. Everyone can do that," but no, they can't, and there are so many superpowers others have that are tremendously hard for me. That's the secret.?

Find yours and supersize it.?

2. Lean In?

I am borrowing from the title of the great Sheryl Sandberg book here (which is a must-read and helped me immensely early in my career). But essentially, be a hand-raiser, be the person who steps in and owns it. It doesn't matter that you don't know entirely how you'll get something done sometimes by just accepting the challenge and stepping in, you're halfway there. The lessons you'll learn by leaning in, raising your hand, and stretching will serve you better than any assignment or BAU activity ever could.?

Leaning helps visibility in your career, and more than that, it helps you find areas where you enjoy being. Lesson 10 here is to have fun but to have fun at work; you want to find where you love to nerd out, where problem-solving seems fun, where you lose track of time, and it doesn't feel like work. Leaning in helps you explore and find other areas and projects that you could explore growing in.?

Also, leaning in and getting as much surface area as you can tells you early what you DON’T like doing, which is likely the best thing I got out of years of internships in college. I learned nothing I was studying or thought I wanted to do in life I wanted to do. That took me the long way around to my 20s in Hawaii and eventually into marketing, then technology. Without knowing that early, I would have wasted so much time. So many recent grads I talk to today want to lock something in early and make that a career. I don’t know; maybe some of you can, but I’d say go out there and lean in.?

I talk to too many people who want to graduate and just go to a name-brand company. That is a great goal if the company inspires you, the work inspires you, no issue. But there is a lot of experience to be earned by going to small scrappy places and getting a real roll-up-your-sleeves experience. That type of grit cannot be taught and is generally harder to come by in larger enterprises. It is almost an individual innovator’s dilemma problem you can learn and bring the grit with you as you go upmarket to larger companies to work; the same can’t always be said the other way around.?

To quote the late great Jerry Garcia, "Sometimes you get shown the light in the strangest of places if you look at it right."

3. Get in the arena?

The Teddy Roosevelt quote below has become trite, especially in tech, but I still love it. Don't be afraid of "failure". Fortune favors the bold, and chance favors the prepared mind.

After leaning in, taking on stretch, and being a hand-raiser, the opportunities and stakes grow bigger, and it can feel daunting to want to take those on. I get it, but you can't protect yourself from not always smashing things out of the park; you shouldn't expect to.?

The average Hall of Fame batting average is .303. Nobody, not even the great Ted Williams (go Red Sox), can hit much above 40% of everything.?

Baseball analogies aside, the goal shouldn't be to stay safe and comfortable. I have found the most fun on the edges by stepping into the arena and figuring it out along the way. Hey, even if you don't hit all your marks, you'll be a different and more capable professional for it.?

As a side note, the secret is that everyone is just figuring it out along the way. (I rediscover this principle every few years, and it shocks me every time.)

Don’t let the fear of other people’s opinions stop you from being in the arena, i.e., speaking up in meetings, putting your ideas forward, and stepping into the light. It won’t always feel welcoming, but trust me, we need you and your ideas.?

If you are just building your confidence to speak up vocally in meetings or that is scary to you, you can start to stand up to get your ideas out there via email, Slack, or whatever. People will appreciate it.?

Follow the New York City subway rule: if you see something, say something.?

4. Stay curious?

Being curious has been one of the best principles of my career, especially when I am frustrated. Sometimes, things just don't work, you can't find a way through, and blockers keep popping up. When that happens, if you can force your curiosity forward, it generally is the best flashlight to get out of the tunnel.?

Curiosity killing the cat is the worst saying ever. A better and more accurate saying would be that curiosity has and will drive innovation and growth that improves humanity.?

The best people I have had the privilege of working with have remained curious. When I retrospectively review most of the breakthrough ideas I've had as part of a team over the years, they have always had curiosity at the core.?

5. Learn to thrive in ambiguity.?

Most of the good stuff is ambiguous. A smart person like you wouldn't need to solve it if it were obvious. If you can find ways and build skills to be the person with a compass in the muddy jungle, you'll do well.?

Ambiguity is present in every major important thing you'll want to accomplish in your career. You need to first learn to be comfortable with it and then find and build your own frameworks to navigate through it to thrive.?

Early career folks won’t have the experience yet to strengthen their decision-making skills to execute through the fog, but one way you can jump levels here is to READ, READ, READ.

Thousands of the best business people to ever live have written playbooks, and for $25 you can learn everything they know. Not taking advantage of that would be crazy! Read them, and you’ll find that you short-circuit your brain in a way that allows you to better navigate uncertainty and have conviction in your decision-making.?

Learn how to do what William Ury calls “going to the balcony” in a confusing moment. Zoom out. Plan out a few scenarios and suggest one.?

Also, most people don’t read, so this is the easiest way to gain an edge.?

This stuff compounds.?

6. Reject mediocrity?

At times, certain places, people, or circumstances will try to pull you towards mediocrity. Reject it! Even when what you need to do "meets spec," go beyond it. And if you feel driven to do great work no matter the place, people, or circumstance, don't let anything drag you to do anything less.?

This isn't about doing simply what is expected of you in a situation. This is about what you want for yourself as a great human trying to make your dent in the universe.?

Set what Jim Collins calls “BHAG” Big Hairy Audacious Goals. Go hit them. You’ll surprise yourself.?

If you find you're in a place that doesn't value that, don't change yourself…change the place.?

Do your best work always.?

7. Be great in the trenches?

Work can be hard, and building great things is really hard. At many points, it'll be a slog and battle. One thing that I've always tried to keep in mind is that, beyond everything else, be a good teammate in the trenches.?

Come out of whatever situation or thing you're in with the people around you saying, "They are great in the trenches."?

Crack jokes, bring levity, bring solutions. People won't forget that, and it will serve you well.

8. Everyone's a leader (especially you)

Leadership doesn't come with a title. Leadership comes in many forms, and there is no right way to lead. Most management books you'll read or be taught will be helpful, but at the end of the day, be you is the best advice I have gotten or could give.?

Be the leader you are. Embrace your strengths and bring yourself to the table. I am undoubtedly outgoing and, as a Boston kid, perhaps a bit too loud, but so many great leaders I know (who aren't all managers, by the way) are quiet. They are kind and compassionate and have different styles to bring people along. Find and embrace yours.?

Leadership doesn’t begin when you get a people manager title. In fact, the same skills are needed in that role or a senior individual contributor role. I’ve led teams and currently have an IC role, and I can tell you I use all the same skills in each role. The IC role is arguably harder since you are influencing without authority and mostly managing out and up.

Leadership is about being a beacon, a lighthouse in a storm. Don't be afraid to step out and lead because the world needs more leaders and people like you.?

9. Pressure is a privilege

If you do everything here and are even still reading this, congratulations. You're probably an A-type overachiever, which is awesome. As someone with a growth mindset who raises their hand, you now have a privilege that can sometimes feel like a burden.?

You will become what Seth Godin refers to as a lynchpin. And as a lynchpin, you'll be incredibly reliable and execution focused. This means the scales of work, trust, and pressure will accrue to you. You can't escape this, so embrace it.?

Take pride in this privilege. It means something great is expected of you.?

10. Have fun?

This is the most obvious and seemingly trivial advice, but for me, the one I forget most often. What are we doing here anyway??

Are we here to push widgets? Should we move papers around like George Costanza as the assistant to the travel secretary sleeping under our desk??

Or are we here to do our best work in the best places with the best people? If it's the latter, then don't forget to have fun. The best way I found to have fun is first to remember that, yes, work can be fun if you're growing, progressing, and making your dent.?

Go make yours.?