Taking A Break From Business: What I Wish Every Entrepreneur Knew

Do you ever get the feeling you’re white-knuckling it through business ownership?

Like if you just squeeze the wheel hard enough and focus on what’s in front of you, you can keep your business from ending up in a serious fender bender (or worse)?

I’ve certainly felt that way. All throughout 2020, I felt like my extreme vigilance was the only thing between my business and an 8-car pileup. And we didn’t get hit nearly as hard as many businesses.

It’s a burden, being able to control situations with my hyper-vigilance, but it’s my lot in life.

— Tina Fey, Bossypants

That hyper-vigilance can look like needing to have my fingers in every project or having to touch base with every customer. It can look like working 10 hours a day or checking in on the weekends. It can look like not going on vacation for fear of things crumbling without me or always leaving my inbox open throughout the day.

This last year involved every one of those habits at one point or another. Sometimes all at once.

Truthfully, I’m still burnt out from The Year Of White-Knuckling.

And I need a break. That’s why, if you’re reading this at the time it’s published, I’m unplugged and on vacation. Note from writing self to vacation self: seriously, let go—don’t work this week.

Of course, “taking a break” isn’t just about taking a vacation. It might mean making space for a creative project. Or making time to work on your business. Or taking Fridays off. Or putting your podcast on hiatus. There are so many ways to take a break from things that drain us (even if we love them) but hyper-vigilance is not the way you do it.

Last year notwithstanding, I’ve led my business to a pretty peaceful equilibrium.

We have strong systems, predictable cycles of work, and a dreamy community of customers who cheer when we take some time off.

But I also catch a glimpse of my former hyper-vigilant self every time I see Sean worry about our clients on the weekends or try to make vacation plans around reliable access to the internet every morning.

While it would be wonderful to work in a world where taking a break meant just shutting down the computer on a Friday with no preparation and not giving work a second thought for 10 days, taking a break takes some work.

There is work to be done on the business—I’ll get to the specifics in just a moment—and there is also mental work.

Now, if you’re not the anxious, hyper-vigilant business owner that I am, maybe mentally preparing for a break isn’t so hard. I have no idea what that’s like. Feel free to skip ahead, though.

For all the worriers out there, probably the most helpful mental shift I’ve made over the years is learning that:

There is no amount of worry or hyper-vigilance that will stop something bad from happening.

I can’t not take a break because I believe checking email every day averts all potential problems.

Ish happens.

Even the best systems, happiest customers, and most independent team members won’t stop the random problem from breaking through.

But just because I can’t stop a problem from happening doesn’t mean that a problem will happen. I can take a few days or a few weeks off without there being a problem that requires my immediate attention. And, in fact, that is the most likely scenario.

The business runs well. Our customers are self-reliant (by design). Our team members are resourceful and self-directed.

I’m not actually holding anything together—even when I’m working 40 hours per week. The business holds itself together!

At this point, you might be thinking: “Okay, Tara, that’s great for you. You’ve been doing this for 12+ years and you live & breath business-building. But I really am holding my business together!”

Noted. And that’s why this piece doesn’t end here.

The fact that I don’t need to white-knuckle my business is a product of design—not talent and not even longevity.

So what does it take to design a business you can easily step away from?

First, I’m going to invite you to let your imagination run wild with all the potential problems you can foresee happening if you take a break.

Where are my anxiety-prone entrepreneurs at? Your were born for this exercise!

  • What if you get an angry email from a customer?
  • What if your website goes down?
  • What if a client needs a change to a big project?
  • What if a team member hands in their resignation?
  • What if? What if? What if?

Every business is going to have a slightly different list of potential breakdowns. So think up as many as you can based on your unique business structure, systems, offers, customer base, team, etc…

Each one of these potential breakdowns is an opportunity for either strengthening your existing systems and/or creating a contingency plan.

Strengthen Your Systems

When you strengthen an existing system, you might build in some redundancies, automate parts that have been done manually, or clearly document the steps in completing the system. The goal here is to prevent a problem that you can see the potential for. This is actually an opportunity to use all of that hyper-vigilance for good!

When you build a contingency plan, the goal is not to prevent a problem but to create the recourse for when a problem does happen. Contingency planning is the ultimate in entrepreneurial realism!

For instance, if you worry about someone requesting a refund while you’re away, how can you handle this in your Out Of Office message?

You might ask them to email a team member who can handle the refund for you or you might let them know that the refund will be processed within 48 hours of returning from vacation.

If you worry about a client needing a change to a big project, how can you preemptively handle this in pre-vacation communication?

You might send out a message to all of your clients 30 days before your vacation to let them know that it’s coming, who their point person is while you’re gone, and when you need materials from them for ongoing projects.

Use Clear Communication

I’ve found that when it comes to people-related problems, the real problem isn’t the problem itself. The real problem is not knowing how or when it’s going to be resolved. If they know you’ll process their refund when you get back, the vast majority of customers are willing to wait. The vast majority of clients will respect your time off if you give them a heads up on when you need materials by beforehand and when you’ll be back at your desk afterward.

It does take some planning but it doesn’t have to be the full-on sprint that we so often turn vacation preparation into.

Do Mental Triage

And when it comes to technology problems? This is definitely harder. There isn’t a good way to prevent most of these and even most contingency plans are going to be lacking.

But the thing with technology problems is that they probably don’t matter all that much.

Would I be upset if my website was down for a few days? Yes, absolutely. But ya know what? It would absolutely not create any real consequence for my business.

Would I be disappointed if social media posts I’d scheduled beforehand didn’t post? Sure, but it truly doesn’t matter.

Would I be annoyed if my PayPal account was inexplicably frozen while I was away? Yeah, but only because I hate calling customer service. There are other ways to pay us.

Identifying potential breakdowns in your business and preemptively addressing them is a great way to put your mind at ease enough to take a real break from work.

And, you don’t have to do all of these things before your next vacation or long weekend.

You don’t have to get your business into tip-top shape to “deserve” a break.

Make yourself a punch list and focus on one thing at a time. Not only will you be even more prepared for your next vacation, your business will be stronger, too.

Finally, knowing what really matters—what actually constitutes a problem and what doesn’t—is the ultimate vacation hack.

But as I mentioned earlier:

Taking a break isn’t just about going on vacation or even putting things on autopilot for a little while.

Sometimes, we need to step away from specific tactics, offers, and methods of operating in order to move forward in other ways.

After The Year of White-Knuckling, I was in exactly this position.

So I wanted to share some things I’ve taken a break from this year in order to free up some space to recharge my brain and body.

The first thing I decided to take a break from was showing up personally on social media.

I was tired of viewing my life through the filter of what was shareable. I didn’t want to have to stop and consider whether my workout, my dinner, or my latest obsession would be a good way to represent myself on Instagram or LinkedIn.

I still inject my own story and my experiences in the work I do—I’m doing that right now! But 99% of what I post to Instagram—the only social media platform I keep up with these days—has been carefully crafted content, not personal snapshots.

This was a tough choice for me. I have truly enjoyed getting to know people on social media. I have loved getting to see inside of other people’s lives. But increasingly, I was inspired by the rich content others were creating for Instagram and exhausted by trying to produce anything quote-unquote spontaneous.

When I initially took this break, I assumed it would be temporary. But it increasingly seems like it’ll be a permanent break or at least a very extended one.

The second thing I’ve taken a break from is being a linchpin.

Being a linchpin is different than being a bottleneck. Being a bottleneck is an operational problem that can often be solved through stronger systems and automation. Instead of every task having to flow through you in some way, tasks can be accomplished without your input or approval.

I took steps to remove myself as a bottleneck years ago. And while it’s still an ongoing process, being a bottleneck in my businesses is largely a problem that’s behind me.

However, I’ve still been the linchpin.

Literally, a linchpin is what keeps the wheels on your car. Figuratively, a linchpin is the person a team or organization revolves around.

Being a linchpin can be an operational problem, but it’s also a branding problem and a value delivery problem.

If your brand and value delivery can’t be fulfilled without you in the middle of it, you’re the linchpin. That’s not necessarily a bad thing! But after the Year of White-Knuckling, I needed to let go of at least some of my own “linchpinness.”

At What Works, that’s meant that I’ve relied more and more on Shannon to host events that add value to our community. In August, I’m actually taking a break from hosting community events and inviting some of our members to step in. And in July, I’m also taking a break from the podcast for the first time in almost 6 years. More on that in a bit.

It also means that I’ve relieved myself from the responsibility to be the chief catalyst of our growth and handed that over to Rita Barry & Co, who runs our ads. That means I can do what I love: writing & podcasting about business without feeling like the entire weight of our marketing strategy is on my shoulders.

At YellowHouse.Media, it’s meant letting clients build a stronger relationship with Sean and Lou so that I’m not the only one who can be counted on for strategy. This has gone exceedingly well!

Until the businesses are much bigger, there will always be things that only I can do—but the more I relinquish my role as the linchpin, the closer I am to being able to fully walk away.

And the third thing I’ve taken a break from this year is hosting groups.

This was a really painful one for me. There are few things I love more in my work than seeing how business owners stretch themselves with the help of a supportive group of people. And for over 10 years, facilitating group coaching and masterminds has been a key part of how I support small business owners.

But The Year of White-Knuckling brought me to my knees when it came to supporting groups. There were so many ups and downs, so many diametrically opposed experiences, so many feelings. And that’s not to say that our groups went poorly last year! Many people have told me that the group support was what got them through the year.

I did my very best to support those groups with everything they needed—and to do that, I ran myself into the ground.

Since realizing that I’m autistic, my experience with leading groups last year really started to make sense. I have to work extra hard to parse an individual’s emotions and nonverbal cues. Group dynamics raise the stakes on this by about 100-fold. Mix in an economic shock, humans who are stretched to breaking by homeschooling, and just general anxiety about whether their businesses would survive to the next week… and well, I was not the right person for the job.

I’m not complaining of course. I love the people we worked with last year. I love the opportunity to guide and facilitate important conversations.

But I’ve learned a hard truth: it’s not sustainable for me.

Will I go back to hosting and facilitating groups? Maybe. I’m honestly not sure. Maybe I’ll find a way to make it sustainable. Maybe I’ll get back to a point where I can take on the work again. But that time is not now.

For now, my focus is on building up my capacity again and finding ways to work with business owners that exhaust me less.

Hopefully, I’ve given you some food for thought here about how you might be able to take a break—whether that’s from work, from a particular offer or type of customer, or from a task that’s draining you.

Cover of What Works book by Tara McMullin

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