Character and Portfolio

The only two things you need to focus for building a career and a life.

A designer I worked with recently asked me for career advice. I believed this since year one of my career and still today: the only two things you should ever focus on, no matter where you are in your career, are your character and portfolio. Both are malleable. And in the long run, they are the only things that truly matter in working with interesting people and solving interesting problems.

Character is who you are. A portfolio tells a story about what you do.

One is about mastery. The other is about reputation.

A portfolio can get your foot in the door. Character is what allows you to stay.

You can also flip this: your character gets you a conversation because of the good things other people said about you, and a portfolio validates the person behind the work.

A portfolio highlights your mastery, craft, taste, and creativity. It tells a story about what you love working on and what you’re good at. It is a body of work. Why are you showing this particular project to me? What change did you make? Did it work? It must mean something to you, and it’s my job to understand why you care deeply. What kind of work makes you light up?

Character is how you behave. Are you a learner or not? Are you self-aware or not? Are you open or not? Are you a loudmouth on LinkedIn or not?

Character is revealed over time through behaviors, not words alone. You can get a sense of one’s character through reference checks, sure. Still, real character shows itself over time, especially in adversity, confusion, and panic.

What about a college degree?

What about learning AI?

What about becoming a prompt engineer?

What about coding, writing, or graphic design?

What about working at a famous company?

What about learning office politics?

What about moving to a major city?

I’m sure some of those things might matter to some people. It’s best to focus on something in your control, which is developing a beautiful body of work with a coherent point of view and becoming someone great to work with. The rest are tactics unique to your environment, goals, and personality.

Whenever I have to hire someone or consider a collaborator, the only two things I spend my time on are portfolio and character. I can dissect a portfolio and understand what the person cares about and what they’re great at. I learn about one’s character through conversations and interactions. The rest is taking a risk and trusting the process.

Some people will look at your LinkedIn and look for a famous company on the list. A famous company signals that 1) you might be good at what you do and 2) it’s a safe bet for the employer. But I personally don’t believe in those signals anymore, no more than seeing someone wear high-end fashion and believing they have any sense of fashion. Titles and famous company logos were useful illusions in the first ten years of the startup zero-interest rate world, but this halo effect has dimmed.

The opposite is often true: working at only famous companies (especially for one year at a time) shows me that the person had a good college education and the right network that got them in the door, but they achieved nothing impressive or meaningful.

I place a strong emphasis on building one’s portfolio—and letting that be the magnet for your next opportunities and collaborators—because I see too much bullshit and smoke-in-mirror tactics in the industries I’ve worked in.

I strongly believe those who build and create, those who can write and tell stories to enroll people in a vision, and those who create the environments for makers to do their best work should be leading. But sadly, the opposite is often true. Those who can’t write/think, those who never built anything, are somehow responsible for the people who do those things.

A strong portfolio and character will most likely get you your next job.

The recruiting industry is bloated, with low barriers to entry that have caused wreckage. LinkedIn is a fucking mess. In the past ten years, tech startups gave free promotions to people who’ve never built anything or done good work. Job titles are utterly meaningless these days. You’re pushing against the tide of mediocre people with fancy titles and no portfolios. No proof of work. Yet, sadly, I see so many of these people in leadership positions at promising companies. They have all the decision-making power simply because of the titles and time spent on the job.

A portfolio is a defense against all of this bullshit. A portfolio is earned over time. Projects get added and removed. Like a bonsai tree, you trim and nurture it throughout your entire life.

Think of it this way: If you wanted to climb Mount Everest, who would you speak to? The person who made the climb ten times? The YouTuber who talks about gear? Or the oil painter who lived in a nearby town? Probably the person who survived the adventure, right? Then you can worry about gear.

For any young creative person building this so-called “creative career,” I hope the way I look back on my history and connect the dots is helpful for you. When I lacked in portfolio, I made up for it in character. When I grew my portfolio to be in the top percentage of my industry with the character to back it, the opportunities started coming to me.

I failed my way through college. Majored in Psychology but wanted a career as a writer on the internet. Started a blog and read a ton of books to be responsible for my self-education and my growth. Wrote 2,000 words a day, every day. A blog got me some freelance gigs. Small gigs led me to bigger ones. Logos on a page to signal expertise and trust.

Having a blog and a decent portfolio of writing led me to my first Content Producer job at a small startup during my senior year in college. My editor and close friend, Sean, was my reference and knew the person hiring for this role because he, too, wrote for the same publication. This was the benefit of character: displaying a hard work ethic, curiosity, desire to learn, showing up, and doing the job diligently. I was working remotely and making $68k a year, which was insane for a 24-year-old. Two years of that taught me a lot about startups, the workplace, remote work, marketing, and online writing. Got laid off because of a shift in the company.

Got lucky. Seth Godin was building a new program called The altMBA, a four-week intensive workshop for people who want to level up. The first CBC (cohort-based course). He thought of me because I attended a three-day workshop years ago and kept in touch via email. Was I considered because of my character? Probably. What was supposed to be an experiment project turned into three years of the most meaningful work of my life. Three years of building a startup, coaching hundreds of students, hiring coaches, building culture, and working with a small team. Learning endlessly. But it was time to move on. Seth Godin was my reference for a new job… imagine that?

Moved to Brooklyn. Joined CreativeMornings to lead and manage their content. Learned community building. Built a newsletter from 100k readers to 250k. Launched global campaigns with cool companies like Mailchimp, WordPress, and more. Worked with thoughtful and generous humans. Did the work of three full-time people, so I learned a fuckton. Made friends in cities around the world. It was a fantastic three years of endless learning, living in NYC, and expanding my circles. Also, I became a photographer.

A portfolio is shaping. Zoom out—this guy can write, build things, and think. Also has taste. Has vision. Can do things from start to finish.

This portfolio raised the eyebrows of a brand agency leader, Brian Collins. A thirty-minute coffee meeting turns into a three-hour conversation about the future, industry stagnation, the future of branding, and creativity. A full-time offer is on hand. I wrote the job description. I join, I lead change, I build new things, I learn authentic branding, and I contribute to some awesome projects like Robinhood, Crane stationery, Match.com, San Francisco Symphony, Clubhouse, and more. I make lifelong friends. I have a cool company on my resumé.

Why did he hire me? Because of character and portfolio. I had the skills he needed (writing, thinking, building audience/community). And because I’m a dogged motherfucker that wants to do great work.

At this point in my career, it’s clear what I love doing. I’m not stuck in one industry. I can work in any industry because every enterprise needs clear thinking, good writing, and cohesive branding. And not once did any employer ask me where I went to college.

Between all of this, I start side projects that fail, try to switch careers and fail, write books that fail, and write articles that fail. I shut down the blog I started in college—10 years of writing, poof. Gone. Bon voyage.

The pandemic fucked me up. I leave COLLINS. Do some freelance brand strategy for a few months. Because of my character, portfolio, and network, my bud Mark Johnson hits me up for a gig. A gig turns into a full-time job. It doubles my salary. In two years, we evolved the brand and shipped dozens of projects. Friends I admire are hitting me, saying how excellent the work is. This is the first time doing something of this scale in-house in a relatively short timeframe. My name is out there.

I’m getting poached. Having calls left and right. For the first time in my career, I have leverage. Leverage gives me confidence. The conversations for jobs are different. I can ask bigger and bolder questions. I can detect all the red flags and patterns quickly. I can feel, in the first fifteen minutes of a conversation, whether there’s frequency or not. I can say no.

Realize this: I am now 14 years into my career. It’s non-linear. I can’t be put in a box. This is good because it’s how I want to lead my life. It is sometimes bad because most companies want you to fit into a box. All good. I love what I do. I love the people I work with. I have it good compared to 99.999999% of the world.

If you’re wondering why you aren’t at the levels you want to be yet, focus on your portfolio and your character. Doing great work attracts others who do great work. And we all talk to each other.

Some people play a different game and collect job titles. Good for them. They figured out a gap in the system and slithered through. The tech startup world is filled with clueless, incompetent so-called “leaders” who have the title but no proof of doing the work. This sharpens your intuition for who not to work for in the future. Working with the wrong people will obstruct your career and your future. There is no greater red flag than an incompetent charlatan with a fancy title and no portfolio, no ability to write, think deeply, and tell interesting stories to set a vision. How these people got their jobs I dunno. That would make for a great best-selling book or Netflix series. The moment you realize you’re working for someone like this, run. Where I’m from, we call them fugazis.

Play the long game. Grow mastery, emotional intelligence, self-awareness, humility, and storytelling. Work on things that light you up. And if your job isn’t giving you those opportunities, nothing stops you from doing it alone other than fear. Find other people who want to build cool shit. Make things and ship them.

Because when you start living like this, other people will find you. They will want to learn from you, work with you, and connect you to their friends. Rather than playing bullshit LinkedIn games or job title games, you can choose what your future looks like when you have a portfolio. When your name is clean and out there.

Every opportunity has a cost. Will it enrich your portfolio? Will it build your character? Will you learn a lot along the way?

Character: Who are you? What do you value?

Portfolio: What have you shipped? What are you great at?

This leads to an interesting question and conversation: Where are you going?