My first sabbatical exposure came at a small consulting company I was a part of in my 20s. They offered a consecutive month off (paid) in addition to vacation every seven years you were with the company.

The sabbaticals were a big deal. People would give presentations on what they did, so they used their time well. I saw hikes across New Zealand, mission trips to South Africa, and road trips with families.

It stuck with me.

To this day, it’s a rare and overlooked benefit. Last I read, less than 15% of companies offer this.

But it also has a direct impact on improving the scalability of your company.

Good for people & good for the company

Mike Michalowicz covers the idea of a 4-week vacation in his book, “Clockwork.” He uses it as a forced march and litmus test to ensure business owners are not handicapping their business by keeping their fingers too deep in the pot. The end goal: Your company should run like Clockwork even if you’re not there.

In my corporate life, we called this mitigating the single points of failure. Or “SPOFs” since that was a mouthful.

As Business Owners, it’s easy to make ourselves SPOFs. I’ve talked to hundreds of business owners in the last few years, and very few see a future in which they could be away for four weeks. 

That’s because in their head — the business is them — and they haven’t put the plan on paper that separates the two.

You can’t leave for four weeks and not plan for it. You think there are all these things you do that no one else can, but with enough time and elbow grease, they can be handed off.

So prove it, Jenny

I know it’s possible because that’s what we do in our Orchestration service. We take all the standard processes you need to run your business and help you work through getting the right ones on paper, and in the hands of your team, in the correct order.

It starts with your first hire — For a lot of people that’s a Virtual Assistant — to handle critical, everyday tasks like email, scheduling, bookkeeping, invoicing, or repeatable marketing tasks, and then moves into a small but mighty team.

Curious? Reach out to Courtney (our Practice Lead) can tell you more.

I’ve been recommending sabbaticals for a while. Last month, when I recommended it to a client, I realized I was getting into hypocrite territory if I didn’t eat my own dog food.

It’s been three years since I brought this company to life and gave it a heartbeat. And it is time for me to take one too.

So we had an internal team planning meeting and realized it could happen with only a month’s runway.

My sabbatical starts tomorrow.

Friday, September 9, after I wrap up my last outstanding to-dos, I’ll be stepping away and letting my team (mostly) run the show.

We’ve agreed to 3 mornings across the 4 weeks that I’ll be checking email and following through on the small number of exceptions we decided to allow. If you have more than a month to plan, you shouldn’t need any exceptions.


Then it’s time to plan yours.

My formula for sabbatical planning

  1. Commit – Telling someone increases the likelihood it will happen
  2. Schedule – Set the date, then back into what needs to happen
  3. Set the goals – What purpose does it need to serve for you and your biz?
  4. Set the rules – Can you be reached? If so, how/when?
  5. Make two lists and determine what will happen with each.
    1. YourGeneral Work
    2. The Projects & People you interact with
  6. Reverse engineer a transition plan to make your schedule work
  7. Work the plan until heads nod that they are ready
  8. Communicate, communicate, communicate. Everyone impacted needs to be clear.
  9. Owner-proof the disconnect. You’re going to be tempted. Remove it as much as possible.
  10. Find an accountability partner. So you know it’s doing what it needs to.

It takes detailed planning to get to this time away, but it is 100% doable. And if you’re stuck, my team can help. Book a coffee with Jess, and she will help you build a plan that works for you.

Because I’ll be (mostly) out of the office 🙂