The Tactical Deployment of Fun

One of the challenges I face working for/by myself is "getting started." I’m a talker, and I’m at least 20% smarter when talking an idea through with someone else. 25% smarter if I can high five and walk around while talking. 

When I’m working actively, talking with a client, we cover a tremendous amount of ground really quickly. It helps that we speak a common client services language and can share ideas in a more primordial state back and forth faster. After a 45 minute call I’m often stunned by how much ground was covered, and how easy it was to plow through a bunch of topics or challenges.

Then, I sit down to do some heads down work, and time slows to a crawl. It feels like the Millenium Falcon coming out of hyperspace. It’s not that I’m procrastinating. I can watch those Joel Embiid videos later. I struggle with the frustration that my rate of progress slows so dramatically.

What I started to do to overcome this frustration, was find ways to make work fun. Well, fun may be an overstatement, but I definitely find creative ways to get rolling.

For example, I needed to rewrite a client’s proposal from soup to nuts (soup to mints? Who eats exit nuts?) and holy crap I was I getting good at staring at this document not getting anywhere. 

So I thought about Dan Mall. If I endorsed Dan Mall on LinkedIn I would obviously start by endorsing him for scarves. The brother’s scarf game is on point. But next, I’d endorse him for making work fun.

I’ve worked with Dan on a few projects now, and where he’s irreplaceably valuable is when he reconstructs a client task to be fun. Whether it’s as simple as using Mad Libs as a metaphor to get clients talking, or exploring an idea visually vs verbally, Dan is great at looking at a challenge from a slightly different angle, and making the work more enjoyable and memorable. Clients come out of his meetings humming. That spoonful of sugar is just enough.

So rather than plow through my client’s proposal, I put on some sweet sweet coffee house jazz and read other firms’ proposals. I have a wee proposal library I’ve built up over the years. I love reading them. It’s a thing. 


I started reading through other examples, and started cataloging their contents by sections, by focus, by structure. Armed with this mighty spreadsheet, I was able to run a gap analysis of where my client’s proposal has holes. Where they comparatively over-invest in content or focus. Where they stand out. Rewriting was a breeze.

I try to think like this when working directly with clients too. 

For example, when discussing business development goals with a client, I often employ a time traveler metaphor, bear with me. When you’re in biz dev, you’re a time traveler. You’re living at least part-time in your firm’s future. The projects you’re closing, the clients you’re calling, they all represent the work your team will be living with for the next six months, or the next year. You’re imagining the case studies this work will yield. The other projects it can lead to in time. You’re thinking 6–18 months ahead.

When developing these goals, I’d love to crack open the client’s Work section on their site, view source, and start to messing around swapping in new client logos and case study titles that represent their wishlist clients. It would be awesome to visually see Starbucks or the NBA or Habitat For Humanity or whatever among their client case studies, on their actual site. The reality of that would be awesome. Frankly it’s just outside my reach to pull that off live (but I know Mark Huot can do it, I’ve seen him do it in a pitch and it’s glorious, damn him).

I can’t stick the landing with my grander unconstrained goals, so I punt. Instead, I have the same kind of time travel conversation without the visual aids, and occasionally I’ll do a bit of that visual work in Photoshop offline and bring that back to the client. That’s what I’m capable of, and it still gets the job done. 

Setting the big, ambitious, fun goal at least gets me thinking in the right direction. Then I figure out how much of that vision I can execute. Ultimately though, I remain aimed at making the process more enjoyable.

It may not always be Disney World-level fun, but Action Park is still a good time. You just need to sign more waivers.