The Deal Is in the Details: Reflections On My First Year as a Principal at Optimist

The email came in last St. Patrick’s Day.

You wouldn’t know it by looking at me, but I’m very Irish. Approximately 55% according to But I digress.

All of that to say, it was a particularly auspicious day for multiple reasons.

I had put in my time—roughly four years—as a freelance content writer, slugging through my fair share of great and pretty crappy client engagements ($0.05 per word whaaaaat!). I built up my portfolio and had done a pretty poor job of advertising myself (save for a professional site graciously crafted by some developer buddies).

Somehow, Tyler found me in the depths of the Interwebs (read: my woefully under-updated profile 🤦🏾‍♂️). He asked if I’d be interested in writing for Optimist. Honestly, this had been the gig I had wished for my entire freelance career. I thought to myself:

Boy, I’ve come a mighty long way since the days of writing $20 per blog post for obscure sites after blindly responding to Craigslist job postings. 😱

With a solid complement of freelance clients and a steady full-time gig that was super flexible, I decided to shoot for the stars.

I pitched Tyler on bringing over my portfolio of freelance clients and slowly onboarding as his first Co-Principal.

I had the sense he wanted to grow the agency and this was my shot to level up starting with the clients I had cobbled together on my own. I flew to Denver a few weeks later and we spent the weekend grabbing meals together, whiteboarding firm strategy, and even tossed in a few late-night brews and hip-hop out with my Denver buddies one night.

Getting comfortable with each other through that in-person time was critical.

We made a gentleman’s handshake agreement to embark on new terrain together. Neither of us knew exactly where the rest of the year would take us.

Tyler had built Optimist from scratch and was taking a huge chance on me. There was no playbook for bringing on a co-principal in a context like this. In turn, I committed to transitioning out of my full-time consulting gig over the next few months.

Playing double duty, it was a slog. In retrospect, this was probably not the best way to onboard a co-principal but it was a necessary evil. I couldn’t give up my full-time income just yet as we felt our way through the right break even point for my full transition.

Personally, I didn’t realize how much I’d have to dig into my personal and professional background to step up and get the job done.

In this post, I’ll outline my high-level learnings from my first year at Optimist. In an upcoming post, I’ll share some of the more tactical moves we’ve made and why.

Relationships are the fuel for our work

My first job out of college was as an 8th grade English and Social Studies teacher in Southwest Philadelphia.

Talk about a baptism by fire.

I was awash in an insane level of details. One hundred and fifty kids and their varying reading levels, family situations, parents’ phone numbers, scholastic history, etc.

It feels awful when you threaten to call a child’s mother—on account of their behavior—only to realize the moment after the words escape your mouth that the child’s mother passed away years ago. Yikes. Detail missed.

As most teachers do, I eventually figured out how to master bizarre quantities of details, develop eyes in the back of my head, and cultivate a strong teacher face (of disdain) that could stop kids dead in their tracks. By summoning the right detail in the appropriate moment, I could persuade, cajole, motivate, and generally infuse each human relationship with the adequate amount of emotional energy to find compromise and progress.

It was my first lesson in sales.

Turns out I’m pretty good at talking with people and distilling down complex concepts into everyday language. I effectively grew up as an only child (though I do have older siblings—a story for another day) so I learned at an early age how to negotiate my way through partnerships with people outside my own family. That’s how only children get by in this world!

Playing to this strength has made me a more effective partner to Tyler and co-principal for the agency.

During those harrowing first two years of my professional career, I would often harken back to my Leadership professor—Dr. Stiles—from my college days and her infamous maxim:

Leadership is relationship.


It’s the most fundamental and cyclical lesson about work. What is work, anyway? It’s just interacting with other humans in a (hopefully) mutually beneficial way. Master those details, foster those relationships, and work will be a pleasure.

I like to think that’s what we’ve built here at Optimist. A (relatively) drama-free workplace where people do what they love in joyful and beneficial relationships with one another. Isn’t that the dream?

One learning I’ve had to take to heart:

The deal you make with a client is sacred. It really freakin’ means something.

Think about it: They are putting their business, their livelihood, their goddamn ability to feed their families—partially in your hands. They give you their hard-earned (or VC-raised) money and they say:

“Help me provide for my loved ones by executing on something I can’t really do for myself.”

That’s huge.

I’ve had to internalize that each client engagement requires personalized and attentive nurturing. Hiba is different from Ben who is unlike Matt who is distinct from Romain who is nothing like Morten.

Not too dissimilar from how I learned to give individual attention to my students in the classroom and schoolwide, I need to bring our team’s gifts to bear for each client in unique ways.

Sometimes this is as simple as scrolling through my starred channels in Slack each morning and thinking to myself: “How can I make this engagement with Client X awesome today? What can I toss their way to make them happy with this partnership, to enrich their work?”

Other times it’s just throwing my noise-canceling headphones on and hunkering down into a great piece of content—the one that’s been sitting open in my tabs all week—and refining the research a bit more, improving the design directions, and making the content even more tactical for busy readers.

When I ground myself in showing up for our clients as people, it makes the world of difference.

The Once and Future Principal

I later went on to become an assistant principal at another school and the importance of details became even more critical.

I had been put in charge of standardized testing for the entire school (both the middle school and high school, around 1000 students and 100 staff). My task was an operational one—set up all rooms for testing, coordinate the flow of students and staff from room to room, nail down the precise schedule.

Man, did I botch that job.

On the very first day of state-sanctioned testing, I somehow mixed up the rooms and duplicated certain schedules. Hundreds (literally, hundreds) of students were stranded in the hallways with no place to go. Teachers were pissed. Students were confused. We risked being in violation of state laws around testing.

It was a bit of a blur, but I somehow triaged the situation in the moment and fixed things for the next few days of testing. I sent a massive apology email to the staff, dripping with self-loathing. I hid behind my inexperience as a first-year administrator and my overwhelm at maintaining a full-time job alongside a full-time academic schedule.

Another stinging lesson on the critical importance of getting the details right as a leader when people (over a thousand in this case) are counting on you.

I share these stories because becoming a principal at Optimist has reconfirmed these early career lessons for me.

I need to slow down, button up the details, and take greater care. If I fail at this, we don’t get the client the high-quality content we’ve promised them. Our professional integrity is on the line.

The biggest shift for me has been translating these lessons from the nonprofit/social sector to the business sector. Before, mistakes like the ones I mentioned had far less of an impact on any sort of fiscal bottom line. Maybe some passive-aggressive emails and some social anxiety, but that was generally the extent of it.

Now, it’s all too real. Gaps in performance mean we as a firm and our clients miss our collective goals.

It’s dollars and cents, now.

I undervalued that significant shift in perspective and through trial and error, have come to realize its gravity. Now, I try to immerse myself in the data on a regular basis to make sure that not only are we hitting our internal marks, but we’re uplifting our clients to hit their goals as well.

We decided to take it slow. I started writing for one client and then managing that same client (somewhat) on my own. It was a bumpy ride at first as I learned the ins and outs of being an account manager in an agency context. I had “managed” clients before, but this was different.

I quickly and somewhat painfully learned a few key lessons:

  • Overcommunicate with clients. (Avoid those dreaded “Where are we on this?” emails at all costs.)
  • Do the heavily detailed research/strategy work (both broadly and within each piece of content)–that’s why clients hire us.
  • Own your mistakes, then fix them, quickly.
  • Show that you’re thinking ahead and looking around corners for and with clients.
  • Constantly make an effort to delight them with the stuff you produce.

Each one of those lessons came from some kind of fuck up. Sometimes multiple, repeated blunders. That was hardest part, seeming to repeat the same mistakes and feeling like I wasn’t learning or growing at times. As with most things, it got better.

My existing clients sort of fell by the wayside on their own and/or weren’t a good fit for the Optimist model of end-to-end content strategy + execution. While I was sad to see them go, I was also happy to be doing much more strategic and frankly intellectually stimulating work.

I was honestly a bit embarrassed that I couldn’t manage to bring over a book of work as I’d initially promised. I didn’t want Tyler to think that I couldn’t deliver. So I committed myself to lighting a fire under our Business Development efforts.

By the end of 2018, I had left my now-previous full-time role, reached 6ish clients in my individual portfolio at Optimist, and we hit our $1MM revenue goal. Getting there was no small feat, though.

Show Up for People

There were plenty of come-to-Jesus conversations.

Sometimes it was my not knowing what I didn’t know. A true skills gap.

Other times it was just sheer inexperience. Not grasping the intricacies of client management.

And still in other moments I was playing too fast and loose with timelines and details. After all, as account manager and principal, the buck always stops with you. If you don’t master the details and insist on those deadlines, no one else will.

I had gotten used to a carefree style of freelancing in which I moved the work around at my leisure for a very small number of clients. There were no shared Asana boards. Content calendars could be flexed. Any blowback affected only me. I didn’t have a team and a business partner relying on me. Now things had changed.

Tyler struck a good balance of being insistent, protecting the Optimist brand, insisting on quality work, while also trying to educate and bring me along into being a full partner for him in this work.

I’m still not there yet.

As our roles evolve, I’m taking a step back to learn more of the research/strategy side of the agency while Tyler  remains heavily involved in that aspect and the ongoing management of all client accounts. I am now pushing into Operations more deeply to ease the burden on that side as much as possible.

It’s not easy to do that kind of relational work remotely, either.

We probably don’t hop on the phone as much as we should—an attempt to value each other’s time I suppose. But when we do check in, we learn from each other and the whole firm is made better.

I want to underscore one very big thing here too.

Building an agency from scratch is no small feat. But trusting someone with your baby is a huge leap of faith. Investing the time and energy to train up that person and backfilling where needed with client engagements as they learn is a tremendous investment of time and energy.

This has been a real-life What Got You Here Won’t Get You There moment. (Great book by the way, go grab it).

Tyler had to level up as a teacher/coach/trainer. He had to learn to let go of some control. He had to let someone else shape and help raise his (now our) baby. I had to learn while doing. Take on greater responsibility for quality and delivery than a typical freelancer. Manage the work of others (again).

At this point, we’re taking stock and creating a more structured plan for what it means to become a partner (on the leadership team) and a principal (managing client accounts) at Optimist. I’m the guinea pig for this little experiment of ours, with the hope that it builds a stronger agency in the long run.

We were and are walking through the unknown together as the work is real-time and high stakes. I don’t know if there’s a way to lower those stakes, slow down, and train in some different manner. And I’m not sure if that other way would even be better.

But I do know that it’s not about just onboarding a new person. It’s about becoming a new team. With every new principal, partner, writer, designer, promotions expert, content strategist, etc.–we evolve into a new agency of sorts with highly dynamic habits for collaboration and production.

That means that processes and procedures need to shift as well. It’s not the sexiest part of the work (I’d much rather be producing dope content for a client), but it sets the foundation for great client work.

Revisiting and shoring up that foundation is critical as your team evolves and your client portfolio grows.

The Joy of Making a Better Internet

We make stuff.

We’re damn good at it.

We’ve convened an incredible team of creatives and digital technicians with a mindset for helping our clients get discovered and grow. We’re growth hackers artists.

We know that growth isn’t a straight line. It’s a trend, developed over time with painstaking effort and optimized precision. This work is part computer science, part prose, with healthy doses of art and operational excellence tossed in there.

I say this to take a step back and contextualize our work in the broadest sense.

The other day, Tyler shared a powerful reflection:

This same idea has crossed my mind in more sentimental moments:

At a roadside cafe overlooking a beautiful bay in Thailand.

Walking through a sun-drenched city park in Mexico City.

Having a beer (outside!) on a balcony at dusk on a summer evening in Berlin.

Those were all actual moments when I was working (or at least thinking through something about work). How #blessed (I hate that meme/phenomenon) are we?

From helpdesk software and restaurant supply apps, to polyamory/open relationships in France and CRM tools—we cover a lot of ground. There’s never a dull moment at Optimist.

We get to spend our days studying cool, fascinating things and educating other people about them. We get to work at our own pace, without overbearing bosses breathing down our necks. We get an escape from the 9-5 grind, untethered from desks and cubicles (nothing wrong with it if you’re into that sort of thing).

We get to make the Internet—arguably the defining town center of our generation—a better, more interesting place.

I try to stay humble about and thankful for that. It’s not about having paternalistic pity on other people for whatever their job circumstances are. This job certainly isn’t for everybody. I know I’m sacrificing my physical health to some extent by staring at a computer screen while seated most of the day. I wish I could integrate more movement into my days. I don’t love feeling shackled to Slack at times.

As with most good fortune, it’s about gratitude. It’s about perspective.

For someone who comes from the education/social sector, it’s a dream to feel like you’re doing some good in this world while also making a solid living. Even better to do it on (mostly) your own terms from where and when you want.

We joke about living the dream, but I think this work comes pretty damn close.

Emerging as Optimist(s) in 2019

Stability is a funny thing.

Just when you think you’re riding high and steady, you get that email or Slack message that upends the apple cart. It keeps you on your toes, but it highlights a fundamental tension:

Growth is unstable.

It’s inherent. If you want to grow, you’d better be ready for some discomfort (the ongoing kind).

My big lesson from this first year at Optimist: cultivate your range.

What do I mean by “range”? I mean being able to immerse yourself in the details like that Google Analytics page with organic traffic results or how precisely to structure that piece on repairing a refrigerator seal while also being able to set broader firm strategy, hire and onboard new team members, and revamp your team’s approach to research for all linkbuilding content.

Toggling between the mucky minutiae and the 10,000-foot view, constantly. That is range.

I know that in my evolving role and given who I am and who I’ve been professionally, I need to lean more in one direction—the details. For myself, my team, and our clients.

More and more, I’m finding that’s where the joy of the work is. And the results.


Paul Perry

I'm a principal at Optimist and lead agency operations. With a background in education and social impact, I help implement performance measurement, documentation, and steer the firm.