Founders and creatives who have had any sliver of success are great at taking action in imperfect conditions. We’ve learned to push through, ship messy, iterate, be cringe.

But as soon as the topic turns to taking a break, or going on vacation, or gasp taking a five week sabbatical, we hedge, saying we’ll do it later, after this next launch, after the next round is raised, or after our dog stops chewing things she shouldn’t.1

We reach for the idealized, Platonic form of a vacation where you get everything you want and none of what you don’t want, where the phone never rings, where you can leave your laptop at home! Your children won’t scream, your plane won’t be delayed, and you’ll achieve a mythical ascension on this here earth.

This desire for perfection, a tendency to hold out until the conditions are just right, prevents founders and creatives from getting the rest that we need.

I’m writing to you fresh from my second semi-sabbatical in as many years. I took five weeks kind of mostly off from work! What! I’m also writing to you in the one week that I am working before heading to Paris for vacation, because that sounds like more fun than working more. I am writing to you as someone who has very little personal savings and who recently blew up her primary revenue stream and and who was severely overbooked this spring and who has fully succumbed to the idea of imperfect rest, to the good-enough time off, to the vacation with the cell phone in hand.

So how did I do it? Am I broke now? Did I fix myself? All this and more in the words below!

Create A Minimal Viable Business

The most important thing you can do to facilitate taking time off is to create a business that supports flexibility all the time, not just when you need it.

I introduced this as the concept of Minimal Viable Business on my old podcast a million years ago. My work on this stems from my experiences with chronic health issues, and the fact that so many of my clients are disabled, chronically ill, and neurodivergent2. The idea is simple: you have to know what the bare minimum is to keep your business alive, and be able to flip the switch to the minimum when necessary.

If your baseline business is something that allows for flexibility, then you will have more access to that than if you have to go into a rigid, busting-at-the-seam company and retroactively create space to do less.

As my business has grown, I’ve honed in on the primary things that facilitate this flexibility for me:

• I run a four-day workweek with Friday fully off from client communication. Sometimes I’ll use this day to catch-up on work, especially if I’ve been sick or had some brain down days. But I never do email or respond to clients.
• I only schedule calls Tuesday-Thursday with a strong bias towards Wednesday, which makes long weekends very easy and also makes it easier to reschedule calls if necessary. if you’re fully booked then it’s nearly impossible to move calls around.
• I only do group calls for my educational and coaching programs on Wednesdays.
• I severely limit the number of 1:1 clients I work with. This keeps down the number of calls and the volume of client communication. My private clients have text and voice access to me during my workweek, so I have to be very mindful of who I work with and how many people I take on.
• I have strong boundaries, including no work communications Fri-Sun, and 24-48 hour response time for different kind of client requests.
• I prioritize scalable offers that require minimal work to maintain.

With this already in place, it was easy to work only a couple days a week, with the bulk of it on Wednesdays.

Enjoying this essay? Subscribe to Think Piece for more deep thinks direct to your inbox 👆

If you have a team, you really need the Minimal Viable Business concept baked into your company. The people that support you must have enough autonomy to be flexible as well. Tools like excellent documentation, full team member ownership of processes, and a great project management system will make it easier for your team to keep working on their own while your gone if necessary. When I took my semi-sabbatical last year, I was in a state of burnout, and had two full-time employees. Unfortunately the team was not as flexibile as I had thought, and it was hard for me to rest during my time off. All of the best systems in the world can’t correct for people being in the wrong positions, and while perhaps counterintuitive I found it much easier to take time off now with less help because I didn’t have to manage as many people.

It was also easy for me to take this time off because I had payment plans running through the month, and due to a very busy consulting season this spring, had some cash banked in the business to pay myself and contractors if everything went sideways. That gave me the confidence to pull back. That confidence also comes from time. I’ve been running a business for seven years now and have saved it from disaster several times. I trust myself and my skills, and know that one slower month isn’t going to make or break my company. This too comes from time. This mental piece, the confidence, was the hardest part for me. I had to really review my past experiences to prove to myself that it would be ok.

My final hack? I picked a slow time of year! I have the data to know that August is rarely a good sales month for me, so pulling the plug was easy: there was no business that I was missing.

I had a lot of questions come through from y’all about the systems, automations, and planning behind the sabbatical, and I’ll try to address those more in-depth in a later newsletter or on the podcast. But the core is this: great boundaries that create flexibility, payment plans and recurring revenue, and easy work that still got me paid while I was off.

So what do I mean by easy work?

Do Your Easiest Work

I did work while I was on my sabbatical, but I made a clear differentiation between the kinds of work that I would do or not do. I know myself well, and can generally do responsive work like coaching or editing even if I’m exhausted, while generative work like writing, product design, or curriculum creation take my best brain. I decided to fully cut-off from all lead generation activities, and focus on the responsive work of supporting my existing clients. I also did not use social media for business and did not create content during the sabbatical. I set-up an email autoresponder that told people they wouldn’t hear from me, and only checked for urgent emails one day per week.

During the sabbatical I was consulting on two launches for clients, and running a group program. So, not nothing! This is work I’ve done for years though, and while it certainly requires thought, it stems from the clients and their needs instead of me creating things from scratch.

You’ll have to figure out what you can do that requires less of you. I feel lucky that my most high-value activities are easy for me, but that’s also on purpose: as I mentioned above, I designed a business that I can run even if I’m sick. I know that I can almost always show up for a live event or respond to a client question even if I don’t feel well. So that is what I chose to allow during my semi-sabbatical, knowing it wasn’t a huge cognitive draw.

Have A Goal But No Major Plans

When I hear people talk about taking extended time off, they often have a lot they want to get done. I think this is a mistake. It’s good to have a goal so your time isn’t formless, but overloading doesn’t give the brain a break. There is probably some min/max time here. Two weeks is definitely not a lot, six weeks starts to get into a timeframe where you may want more plans. For me, I wanted to catch-up on some mending and cleaning, get my sewing machine fixed, and go to the beach. The little things that linger and tend to fall behind during a busy season.

Be mindful not to overload. This isn’t a productivity exercise. It’s an opportunity to change your context and see how you respond. By breaking the habituation of your business, you’ll not only get much-needed rest, but be able to interrogate the assumptions that are dictating your actions. Make sure you give yourself enough time and space for that shift to occur.

Taking extended time off is suited to focusing on some kind of goal. A sabbatical is not a vacation.3 For founders and creatives, an extended period of time with no structure is unlikely to be supportive, and can provoke anxiety, depression, and existential crisis. Pick something to do, just not too much. This isn’t your job, it’s your life.

I had one primary goal: to work on my novel and write a minimum of 1000 words five days a week. My secondary goal was to work on my physical strength through indoor bouldering as I continue to recover from a Covid infection in August 2022.4

The book was the thing though, and gave me the intellectual and creative stimulation that I need. Your thing may be less generative, and that’s fine. Maybe you want to run a few times a week, or read that book that’s been on your nightstand for a year. Maybe you also want to get the stains out of ever piece of clothing at the back of your closet!5

In practice, I worked on my book for about an hour each day, did client work maybe 5-10 hours per week, and the rest of my time was for my family, for doing nothing, for mending. My husband and I prioritized going out for fun dates6, and I spent a lot of time playing tourist. I ended my sabbatical with 44,000 words written for my novel, am able to climb three days per week again, and had a blast bopping around the city. All wins for me.

Be Realistic

I had hoped to emerge from this time refreshed and full of ideas. Maybe if I had completely stopped working, I would have, but that is beyond the realm of what I can manage at this point.

I found instead that it took me over four weeks to even think about generative business activities. I had no inclination or desire to business at all. And now, I’m kind of tired. My brain is not really functioning well this week.

Even during my time off I still had a lot of the problems that I associate with overwork. I got a sick three times. I had several no-brain days. It was helpful to see those uncoupled from a busy schedule, and recognize that they may just be my baseline at this point. I found that freeing, and am happy to know that it’s not my work specifically that is causing those issues. It’s just me, and I have a lot of tools through my flexible business to keep creating the impact I want.

Being back at work has been hard.7 The generative work of connecting with potential clients, building workshops and courses, and writing this newsletter directly conflicts with my desire to work on my novel and have a fulfilling creative life outside of the business. I am finding that the mental difference in being “on” is huge, and even though my day-to-day is not so different as it was during my sabbatical, my stress level is up tremendously. This is interesting information, though, and suggests that most of my problems are in my head. Shocker, right?8 There is something in how I relate to my work that is provoking the strain. Is it possible for me to bring the sabbatical approach into my general work life? Can I find the ease and spaciousness that sustains me while still producing what is necessary to find new customers?

I’m going to try.

---