How to know when it's time to move on

When your dream job becomes handcuffs and you gotta become Houdini. 🪄

In last week’s post, I talked about creating my dream job. The event I mentioned was in February 2018. By September that same year, acquisition talks for Design Milk had begun.

If this was my dream job, then why did I sell the brand?

The honest answer: I’d taken it as far as I could without help. There were things I wanted for Design Milk that I couldn’t financially tackle on my own. I needed to figure out my next move.

Here’s what happened:

In 2017, I was in Vancouver for a design event with a few blogger friends¹ and we were having lunch. I don’t recall how it came up, but we began talking about selling or moving on from our brands.

“I am feeling a little trapped. I need to figure something out. I give it five more years,” I said.

I was stagnant—and so was the brand. When you’re too stagnant, you get comfortable and things are easy, but you don’t grow. I was itching to grow and needed a forcing function, but had to figure out exactly what would be best for both me and the brand.

I worked so hard for so long, and I knew I had limited bandwidth left. I was stressed all the time. My health was declining. My decision fatigue had fatigue. I’d been tired since 2015 and was burning the candle at both ends, knowing there was a time limit.

How did I wiggle free from these handcuffs?

I considered my options:

1. Hire a business manager or CEO - I coudn’t do this because even if I gave up most of my salary to pay this person, I still didn’t have enough money left over to invest in whatever we decided to do. We’d still have had to figure something else out.

2. Merge with another business - Not really an option I was interested in at the time.

3. Acquire another business - Who? and with what money? See #2.

4. Take on investors - I really didn’t want to answer to other people, nor did I want to be beholden to them. Maybe this is short-sighted or egotistical or control-freakish on my part, but guess what? It ended up like this anyway.

5. Sell the company - The most viable option, depending on the deal.

Maybe there were other options, but I didn’t have much time to think about them because EXACTLY ONE YEAR after that lunch, during THE SAME TRADE SHOW in Vancouver, I got the phone call.

And EXACTLY FIVE YEARS after I said “I give it five more years,” I departed Design Milk, freeing myself from the dream job I’d built.

Never underestimate the power of saying what you want out loud. I also advise writing it down in an active statement, like an affirmation.² This is some real woo-woo shit, but I can’t tell you how many things have worked out once I shifted my energy in this direction.

But I can’t say that any part of the process was easy. I worked my ass off to build a brand that was worth something, and I worked equally as hard to remove myself from it. It was one of the most challenging things I have ever done in my life… emotionally, mentally, physically.

No regrets.

Who said you can only have one dream job per lifetime?

1. Writing “blogger friends” makes me feel old but they are O.G., too, and this was my first instinct over ”influencer,” which is what they’re called now.

2. “I am" or “I have” vs “I will” or “I want”