I Have No Idea What I’m Doing

You’d think after more than nine years of being in business for myself, nearly a decade working for others before that and successfully completing a rigorous master’s degree program, I’d have a better sense of how things work or why I’m successful or simply what the fuck I’m even doing, but I don’t. This might also feel strange coming from me after having the best professional month of my entire career, revenue-wise.

But the truth is I have no idea. Or at least it feels that way. And I’m convinced all the people I like and/or respect must feel this way, too. Because anyone who confidently tells you they have the unlocked the answers to life’s biggest questions (broken down by their specific verticals – business, relationships, wealth generation, whatever) is either a fundamentally clueless idiot or a shameless grifter.

This is why my general posture toward life coaches, leadership coaches and the entire self-help industrial complex sits comfortably somewhere between suspicion and outright contempt. I’ve known too many “leadership coaches” who are just dull corporate washouts that ran out of institutions to milk for money and instead started peddling their own rictus-grinning brand of sophistry to people even dumber than they are. Stupid people always have more answers than questions, and it never hurts to be reminded of that, especially when around every corner there’s a “solution” to any problem you can conjure.

I go into any project, any partnership, any collaboration brimming with questions. My professional role, especially as a consultant, is as a shepherd on the road to deeper understanding. I don’t know my clients’ businesses as well as they do, so all I can do is poke, prod and probe and hope that by asking the right questions, clients come to deeper understanding about themselves. Because I think that’s all any of us is truly doing if we’re generally pure of intent and being intellectually honest about ourselves. I also think this is the primary reason why I often feel like I have no idea what the hell I’m doing.


When I started at the PR firm in 2007, I was brought in to work specifically on one of their largest accounts, an account I had fairly deep familiarity with because my previous job intersected with them quite a bit, too. Within a month of getting hired, that client scaled WAY back and I figured I was going to get let go. #PRagencylife, amirite?

I wasn’t. I got re-assigned to clients I knew comparatively much less about, and just had to learn as I went along. The complicating factor was that my account lead on much of my work was our 70 year-old chairman who at the time was in the process of losing his foot to diabetes and spent multiple hours a day doing hyperbaric chamber treatments in (what was ultimately) a futile attempt to save it. I was 26 years old and cosplaying as an account manager. Deep end, kid. Figure it out.

When I started my corporate job, on my literal first day of work, my boss – the man who hired me – came into my orientation meeting and told me he had to hop a flight to DC and that he’d be gone all week. What should I do? “Get familiar with the company, meet some of our key folks, and I’ll be back when I can.” I think I spent a grand total of four hours with him in my first month of employment there. When I finally got a chance to catch up with him in the down week between Christmas and New Year’s, I asked him how I was doing and he told me he couldn’t have been happier. Why and how I’ll never be know, but whatever, just keep doing what I’m doing, I guess.

When I started Jon of All Trades, I began by cold pitching friends and acquaintances who did interesting things for a living and interviewed them. I had started a website before and I’d been a radio DJ before, so those rhythms were at least sort of familiar, but this was me, and me alone, on every single aspect of keeping the engine of this show humming along. I kept going. I seized opportunity where I could, transitioned out of corporate, built my business brick-by-brick, and here we are today.

It’s not to say I didn’t have ANY support in any of those three cases, as I absolutely did and have worked with some dynamite people along the way. I am intensely grateful for all of them. But on a fundamental level, I have a career that could be largely characterized as me making this shit up as I go along. Every stop has yielded new challenges, and I tend to find myself in places of untilled fields, untapped opportunity, and unsupported structure. People look to me and say, “Ok, so what do we do now?” And frequently I’m like, “I don’t know. But let’s figure it out together.” And then we do. Or we don’t! But goddammit, at least we’re trying.


I went to the Kentucky Derby with a large group of friends a few weeks ago and a conversation from that trip has stuck with me. It was me, my wife, and our friends Adam and Michelle. All four of us, either presently, or at some point in our lives, have owned our own businesses. Adam was my accountant, and to this day is my favorite accountant I’ve ever had. He was GREAT at it, but found the work unfulfilling, so he trained his ass off and became a firefighter in middle age. I’m sure he’s great at that, too.

Michelle is a Realtor in Colorado Springs, and was recently featured in a long, very well-written piece in The Colorado Sun. They gave her the hammer to conclude the piece where she said this: “I think there’s plenty of business for anybody who wants to do business. If you look at the numbers and get into the weeds a little bit, you’ll find that a quarter of them don’t do any (sales) and then another quarter maybe do one or two transactions a year,” she said. “It’s like the old 80/20 rule where 20% do 80% of the work. I don’t really worry about it. I figure if I put my nose to the grindstone and work and meet people and be part of the community, honestly, there really is enough work.”

What you don’t hear is her trumpeting her own greatness (even if I personally happen to think she’s pretty great). You don’t hear her telling people she’s cracked the secret code to success. Read that quote again. “I figure if I put my nose to the grindstone and work and meet people and be part of the community, honestly, there really is enough work.” Not I know, but I figure.

I don’t want to assume too much about her mindset because overly inferring from this quote alone is deeply unfair and she’s not here to weigh in, but to me that’s someone who understands that you can never know where or how success is exactly going to come. Basically, all we can do is work hard and be nice to people.

The conclusion we came to after some minutes of conversation is that it truly doesn’t take much to be good, and that so few people do the absolute bare minimum to even aspire to be good. The world is a classroom filled with people who showed up to class and didn’t do the reading, and then complain about how hard the fucking class is. All you had to do was the reading. It’s not that hard to be good.


Once again, I have no idea what I’m doing.

What’s simultaneously reassuring and deeply troubling is that I’m pretty sure most people don’t either. We’re all just doing our best with terminally incomplete information. I don’t take anything in my career for granted. The lessons I’ve learned have been hard-won. The insights I’ve gained have come at a cost. Frankly, it’s sometimes exhausting.

When I say I have no idea what I’m doing, I mean that my advice for maintaining a successful business is shockingly underwhelming relative to most people’s expectations. Even I can’t believe I get to do this for a living, so I still stare at my own life with slack jawed amazement. The only real advice I can give is to do good, honest work that you’ve put effort into for whoever has decided to pay you. Produce work you’re not embarrassed of. Keep your eyes open for people with similar values as your own, and work with them as much as possible. Success, notoriety, and financial rewards are byproducts of these efforts. Your personal integrity is worth more than whatever you sacrifice for it.

This advice feels facile, but when I’m in the thick of trudging through my neuroses, it’s about all I have. I feel myself slipping into cliché, and I hate that. And there are days I really hate that I don’t have deeper insight into how I get this shit to work or what it means or who I am or blah blah blah blah existential angst, for the win.

Today was one of those days. I’m consumed by the overwhelming, crushing weight of the feeling of having no idea what I’m doing.

So I did what I sometimes do when I’m feeling this way. I grabbed a Coors. Here’s what my bottle cap said:

Touche, universe. Maybe it’ll all be okay and this will pass. Maybe just get back to work and calm down.

I mean… what else is there?

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