What should I be working on?
Thoughts on weekends, hobbies, and finding balance when you’re building something you care about.
The internet is a minefield of advice for entrepreneurs. Sometimes you connect with nice people. Often you’ll read something that makes you want to throw your phone.
This weekend there were 2 completely out-of-pocket posts on my Threads feed (follow me there!)
Weekends and hobbies were just minding their business working at making well-rounded, rested, whole people, and got hit with these stray shots.
Both of these posts were clearly ever so carefully engineered to enrage people into writing angry responses. I’d hope that if you sat these two humans down privately, they would admit that they do indeed spend their Saturdays on bike rides, at the movies, rearranging their stamp collections, or something else equally boring but fun and unrelated to work.
So because I literally don’t believe them, I won’t spend time picking apart their arguments (the comments took care of it).
I want to talk about the complicated kernel of truth I felt in these posts under the ridiculous packaging of “let’s cancel weekends and hobbies.”
I think what both of these posts could be saying is:
When you find work that is aligned with what you’re meant to do, it is really gratifying and also really hard to put down.
I’ve discovered that, in my experience, there are 2 types of hard work.
Should Work — Work that you feel you should be doing. This is anything that you think a person like you with goals like yours should do to achieve those goals.
Should Work is hard because it lacks clarity and focus. A part of you thinks you should do it, but a bigger part of you hasn’t fully committed to it. So it’s confusing and leads to procrastination and perfectionism.
Aligned Work — Work that you know is yours to do. This is when work feels exactly like what you’re supposed to do.
Aligned Work is in service to the person you’re becoming. It’s hard because it challenges you, puts you up against your own limits, and invites you to grow past those limits.
When you have a job working for someone else, what you do might more closely resemble Aligned Work. You may not love everything you’re doing, but there’s a certain satisfaction that comes from having clarity that you’re doing what you agreed to do and then getting paid for that.
When you’re an entrepreneur, it is a lot messier. There’s no blueprint, no job description, and very little clarity. Most of us end up doing a lot of Should Work on the way to figuring out what our version of Aligned Work will actually end up being.
My hunch is that we are at a greater risk of burning out when we’re working really hard on Should Work. It takes extra cognitive energy to commit to doing tasks that in your gut don’t exactly feel right. At least this is what happened to me.
Step 1: Find Your Version of Aligned Work
When I was building a startup a few years ago, I worked long days and was exhausted all the time. It always felt like we were behind, and it seemed like I didn’t have enough hours. Everything felt hard and I indeed sacrificed most weekends and hobbies to spend more time figuring it out.
When I decided to focus my career on community businesses and found a business structure that felt aligned, I immediately saw a difference in how I showed up to run the business. I now work less but get more done. I have a much longer timeline for myself and the growth of the business, I make decisions faster, I don’t care if strangers disagree with me, and I am way less hard on myself.
For me the journey from Should to Aligned Work required shutting down and starting a whole new company. But I think for most entrepreneurs, the transition can happens within their current company. It’s a subtle shift in approach.
What I learned on the way to finding what I now consider Aligned Work:
Take note of sentences you say/write that start with “I should.” Whose voice are you hearing in that? Where is your voice?
Find people you genuinely admire to follow and get inspiration from. Don’t pollute your social media feeds, inbox, or calendar with advice you only half agree with and with people whose lives you wouldn’t want, those people are your “shoulds.” Long term it becomes way easier to ignore this.
Every week, block at least an hour for complete freedom to explore within work. Take note of what you gravitate towards when you have permission to do whatever you want.
Simplify your goal, then continue working to simplify it until every morning you know exactly what your job is.
If you commit to practices that help you find your version of aligned work, at some point along the way, things start coming together. Your role in your business becomes clearer. You know what your job is, decisions need less deliberation, and everything starts growing and rolling along a little faster. You’re able to delegate the shoulds and most of your day starts to fill up with the stuff at which you’re literally the best in the world. It feels great.
My goal is to get more community business founders to experience this feeling because it is magic.
Step 2: Don’t Let Aligned Work Consume You
I used to think I would reach a point when work was so meaningful to me that it wouldn’t feel like work. I no longer think that goal makes any sense. Work that is meaningful isn’t easy. The meaning, in my experience, comes from the sense of growth you get when you push yourself and get uncomfortable.
As with lots of things that make you feel amazing, Aligned Work has a dark side. The bad news about finding the right work as an entrepreneur, from someone who has been lucky to be deeply in it for the last few years:
It’s hard, and in many ways harder than Should Work.
You’re growing in real-time, which is not fun in the moment.
It’s addicting. It’s easy to become obsessed with it and prioritize it in favor of other parts of life that also really matter to you and make you a whole human.
The truth is that if you’re ambitious, finding balance is a constant practice, not an end state.
Aligned work is good and is something to strive for, but we can’t be so obsessed with it that we neglect our families, and forget how to be a functioning human outside of our work. The ideal is aligned work that we don’t take 100% seriously.
Here’s what has worked for me to find balance between working hard and not letting the work consume me:
A seasonal work schedule
There are weeks and months when I’m engrossed by a project and working very long hours to get it done. There are other times when I’m not working on one big project. During those times, instead of feeling anxious and trying to find new ways to fill the time, I take the opportunity to rest. Communities naturally have intense and calm periods. Building those into my schedule has worked well.
Friends who help you get over yourself
I’ve made a lot of work friendships with people who know me through the business I’ve built. And I also stay in touch with old friends who have no idea what I work on all day. They remind me of the things that have been true about me, regardless of my job. They would keep me in check and love me, regardless of how successful I get on the internet.
A practice of grounding yourself in your insignificance
As much as the business you’re building is the center of your world. And as much as the members in your community and students in your course might admire you and what you’ve built, you and what you’re building don’t actually matter that much to the world. If you disappeared tomorrow, life would go on. That sounds like a bad thing, but to me it’s completely liberating. It helps me to prioritize the people and the work in front of me, instead of some future state.
And lastly, to find that balance, I highly recommend finding hobbies and taking weekends off. 🙃
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