The Regroup System
The more chaotic life gets (dog → spouse → kid → kid), the more valuable a Regroup System becomes.
Everyone reading this probably juggles five categories of “stuff”: family, work, health, friends, and a side project or startup idea.
Your urgency hierarchy for that stuff probably looks something like this:
Family
Work
Health
Friends
Startup Idea or Side Project Du Jour
For most of you, the goal is to eventually replace #5 with #2. But, realistically, until #5 is making money, it’ll be relegated to the time scraps left by the other four.
The whole Tacklebox program is set up to help you make progress on something that’s low on the priority totem pole, but there’s one specific practice I wanted to pull out and highlight: a Regroup System.
Ideally, you work on your business consistently to remind your subconscious it’s important. But, no matter how good you are, you’ll miss days (or - gulp - weeks). And each day (week) you miss makes it harder to get back on the bus.
I’ve seen tons of founders quit on ideas because they took a few weeks off and getting “back into the swing” was too daunting.
So, here’s my two-step Regroup System.
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The Regroup System
Part 1: At the end of each working session, spend 3 minutes writing out long-form (no bullets) what needs to be done next.
I built something in Airtable using their AI (pretty fun) to track the progress on the startup book I’m writing (sign up here to be an early reader). Each day, I log words written + where I left off / what’s to be done next.
Here’s yesterdays:
You can write this wherever you’d like - a to do list, a daily email, Notion - wherever.
Now, if I go a few days without writing because the aforementioned dog → spouse → kid → kid gauntlet needs me, or if something in the Tacklebox world needs extra attention, it’s much less intimidating to pick up where I left off.
And that’s the key - you don’t want to have to “ramp up” each time you sit down to work. That’s intimidating. We want the barriers to working to be low. The idea behind our 5-minute lists.
Pretend you’re handing the project off to a coworker after each session - here’s what got done, here’s where to start.
Part 2: Don’t let yourself go two days without doing something
The best diet advice is to never let yourself eat two unhealthy meals in a row. If you walk by Emmett’s in NYC and need a little deep dish, go for it. But your next meal has to be healthy.
This doesn’t sound that drastic, but it’s wickedly effective because it gets your subconscious involved. You aren’t the type of person to let your health slip. You never have downward momentum.
The startup version is to never go two days without doing something on your startup. Read the notes from your last session and spend 5 minutes on whatever the next task was. Do this before you go to bed or while you wait in line at Starbucks. That 5-minute check-in will decrease the intimidation when you have a 30 or 2 hour chunk of time in the future.
Startups slip away when they start to feel intimidating to get back into.
These two practices will help you keep the momentum.