P R E S S THE PICKLE
OUT THE WINDOW FLEXIBILITY TRUMPS PLANNING. EVERY T IME .
ve been living out of a suitcase since April. Not only is that something I never thought I’d say, but it’s something I never imagined being able to do. I don’t know what’s crazier — the fact that I’ve been more or less homeless for 16 weeks, or the fact that it actually feels kind of normal . Don’t worry, I’m not hanging out in a cardboard box down by the river; my family and I actually planned this out months in advance. But executing that plan has led to a whole lot of insight about planning, structure, and the most important asset of all: being flexible enough to accomplish a goal in different ways than you originally anticipated. I’
This all started with two months in Belize. We’d planned that trip for a while, and I went into it with big dreams: blogging every day, running the company from another hemisphere, and proving to myself that I could earn what I needed to from anywhere with an internet connection. Like all good plans, mine did not survive contact with the enemy. In this case, the enemy was sunny beaches, tropical breezes, and my kids playing in the surf. Without a structured workday and routine I wasn’t able to do everything I wanted to, and I started getting really frustrated. There I was in a tropical paradise, and I felt ready to go home at the end of the first week.
here with my family, and I had all the time in the world to spend with them. Around week three, I realized that I needed to rethink my priorities and expectations. When was I going to get this chance again? Instead of hanging on to an outmoded way of thinking, I flexed. This led to a massive transformation in my priorities, and it changed how much fun I was having. Hanging on to my plan was just making me unhappy. I shifted toward the positive, had fun with my kids, and I didn’t look back. Believe it or not, work still got done, and Design Pickle had a great Q2. “Around week three, I realized that I needed to rethink my priorities and expectations. When was I going to get this chance again?” We’re back in the States, but I’m still flexing. I’ve learned to simplify my belongings (and do laundry more often). We’ve lived here and there, couch surfing and staying with friends while our house gets finished. And we’ve had fun with each other, which is perhaps the most important
part of all of this. Having a system and a plan is great, but sometimes you need to write a new plan. Don’t get bogged down in past expectations. We live in the present moment, and we can adapt if we need to. That’s what I’ve been doing all summer, and I’ve been a much happier man for it.
The plan had been good, but it didn’t deal with the reality of the situation — that I was
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