I was CEO of an agency for 25 years. Now, I’m setting up my own one-person shop. I’m going to keep a diary of the transition. Here are lessons learned in my first six weeks:

No One Knows Who The Hell You Are

Wow, was this a wakeup call. I strode into my first client pitch soooo full of myself.

The prospect looked at my website and said, “You’ve only been in SEO for six weeks?”

Wheeze.

Lesson: Humility is essential. You’re starting over. If you start to say, “Do you know who I am?!!,” punch yourself in the sternum.

Lesson 2: Make sure you lead with, “I was the CEO of Portent. I started the agency in 1995. Now I’m out on my own. Do you know who I am?!!”

Working From Home Is Great

Until it’s not. I love it. But I can’t find anything in this place.

I’ve asked my wife the location of the refrigerator, the pantry, the printer paper, and my Hydro Flask so many times she probably wants to stab me the left buttock with a steak knife.

Lesson: If you share your space, remember you are not the only consultant. You just have a different job.

People Still Use Stamps

They pay invoices with checks and send bills in paper envelopes. They write contracts and ask for scanned copies.

What the hell?! This stuff takes time!

Lesson: You’re going to have to handle the details, and those details take more time than you think. Plan accordingly.

Grooming Is Essential

Your commute is fifty feet. You should still shower occasionally. Maybe even shave. Rolling out of bed and into your office leaves your brain behind.

Lesson: A routine helps you kick off your day and gets you into a working mindset.

Close Open Loops

I’ll finish my website later. Business license? Oops. The half-assembled cat condo right behind me? It can wait. File cabinet? I’ll move it upstairs next week.

Unfinished tasks like these turn me from a high-functioning neurotic jangling nerve pile to a barely-coherent babbling basket of intellectual lint.

Lesson: Exercise task discipline. Set tasks and finish them. If your brain has the same defective wiring as me, leaving unfinished tasks compromises your ability to think and work.

Noise Canceling Headphones Are A Must

For me, the biggest change in my environment has been the background noise. I used to hear office conversations, calls, and deliveries. Now I hear our dog barking his head off because a leaf landed on the back deck.

Lesson: You can’t tune out new distractions. You’ll need to adjust. Mitigate when you can tune out when you can’t.

Cats Are Jerks

Did you know a cat can actually disconnect a Zoom call by pawing at your keyboard?

Lesson: I wish I had one. My cats are too cute to microwave, too persistent to ignore.

More To Come

This series is equal parts therapy, teaching, and entertainment. Or 90% therapy. You be the judge.

More when relevant.

After 25 years running Portent, I’ve decided to head out on my own.

I was not “forced out.” Nor did I leave because I don’t like working here. It’s just time. I’ve spent my entire adult life (give or take a few years) running an agency. I saw us grow from one person to a team of forty. We were acquired.

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