I’m the person a few years ahead of you.
That’s not a positioning line; it’s a job description.
Twenty years ago I joined a months-old consultancy. Today I still operate one. The work you’re staring down is work I did this quarter and will do again next quarter: positioning, pricing, proposals, pipeline. Advice ages fast in this business. Mine has to stay current, because I still have to use it.
DesignMap started the way a lot of firms do. Two of my classmates from RISD were doing contract design work at Cisco, and the work outgrew them. They had an advocate inside who kept sending more. They brought me on, we hired our first employees, and over the next two decades we grew to fifty people.
Here’s a detail I didn’t appreciate at the time: our first real website came after the work already existed. We never faced the blank page asking who we were. A client had already answered it for us.
That luck had a bill attached. Because the front of the cycle was handed to us, we learned positioning, pricing, and pipeline the expensive way. Not in four months. Over the first five years. We priced by the hour and found out why you shouldn’t. The lessons I teach now are ones I have receipts for.
People assume twenty years at a design consultancy means twenty years of designing. Mine didn’t work that way. Of the three partners, I’m by far the most introverted. I was never the one running the big workshop or delivering the big pitch. My partners carry that side of the firm, and DesignMap doesn’t work without them. My seat was the small room: one-on-one discovery, working sessions, the long-trust client relationships. And behind that, the machine itself: proposals, pricing, pipeline, operations, contracts, procurement. I went to art school, not business school, and then spent twenty years getting the education anyway.
Some of that education came from people decades ahead of me. I still remember sitting with the COO and the CFO of Stone-Yamashita Partners while they taught me utilization and realization, so our firm could predict its revenue instead of being surprised by it. More than once, someone a few years ahead pulled me forward. This practice is partly me taking that seat.
Watching our industry get rearranged these last few years made me ask a question I’d never had to ask out loud: what would I do if DesignMap didn’t exist?
I did what I’d tell you to do. I took inventory. It surprised me: I was trained as a designer, but the deepest expertise I’d built wasn’t design. It was the work around the work. That’s where the hours had actually gone.
At the same time, I was watching people I respect get pushed out of enterprises with their expertise fully intact and their footing gone. They knew their craft cold. What they’d never had to own was everything around it. That part, I knew. The gap was hard to unsee.
One more honest thing. When we started DesignMap, we didn’t know what we didn’t know, and that ignorance was a kind of subsidy. You don’t get that subsidy. Twenty years inside companies means you can see exactly how much machinery you’re about to take on. That’s why this feels harder for you than it did for us.
Your hesitation isn’t a character flaw.
It’s accurate perception.
Why not ten years ago? Because I didn’t know what I knew. The expertise was accumulating, but it was tacit: things I did all day, not things I could teach. It took twenty years of doing the work, and then the discipline of writing about it, to distill experience into something I could hand to someone else. The distillation is recent. The experience isn’t.
Coaching is the newest practice in my portfolio, and I treat it the way I’d coach you to treat yours: named, priced, and structured honestly.
It’s on its own first lap. The twenty years behind it are not.
Confidence is an output, not a prerequisite. You don’t talk yourself into feeling like a consultant. You earn the feeling with evidence: a positioning statement you believe, a price you can say out loud, a proposal that gets signed.
And to be precise about what that means: the artifacts aren’t a shortcut around the thinking. They’re the proof of it. A positioning statement you believe is downstream of real discovery: research, conversations, small experiments that tell you what your market actually values. You already know this discipline. It’s how you’d approach any design problem: make sure you’re solving the right problem before you build the thing. The lap points that rigor at a new subject: your own practice.
Most advice starts from a blank slate nobody actually has. Your runway, your family, your risk tolerance: those aren’t obstacles to the plan. They’re the plan’s inputs.
I won’t promise this is easy, and I won’t pretend you couldn’t do it without me. Most people can, eventually. My job is to make the lap shorter and the lessons cheaper.
If this sounded like your situation, the next step is a conversation, not a commitment. Book an intro call: thirty minutes, free, and the job is finding out whether this is a fit, and pointing you somewhere useful if it isn’t.
Prefer email? Drop me a note at hello@gregobaker.com.