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Can I afford to take a Vacation?

The short answer is Yes, the long answer is it might not be what you think of as a vacation

Whatever downtime may look like, it’s needed. Our brains and bodies can’t handle the constant pressures and decision-making routines for ever-lasting time periods.

Read Time: 6 minutes

By: Heather Wentler – StartingBlock Madison Entrepreneur in Residence

It’s that time of year when we’re all looking to get that perfect vacation photo or video to post on our social media to highlight how we’re relaxing and soaking up the summer. But, can you and your venture afford a vacation?

Downtime is necessary

I remember reading this article a few years ago about Patagonia founder Yvon Chouinard’s belief in time away from work. The quote that sticks with me to this day is “Patagonia employees are hired for their independence. ‘Ant colonies don’t have bosses. Everybody knows what their job is and they get their job done,’ says Chouinard.” This article, and overall philosophy, was before work from home was common-place. More importantly, it implies a workplace culture that supports team members as being successful at work because they’re recognized as individuals.

Whatever downtime may look like, it’s needed. Our brains and bodies can’t handle the constant pressures and decision-making routines for ever-lasting time periods. It’s important to make time to recharge, embrace the slow seasons, and respect our team members’ need for down time within work where they can maintain for a bit versus always being in build or sprint mode.

Preparing for time away

  1. Planning when to take a vacation or time away may have many variables.

  2. What are your sales or big push cycles? Knowing your “seasons” helps plan actual time away without interference from customers & clients or missed opportunities

  3. How much time can you afford to take away? This could mean literal dollars in your pocket available or based on team restrictions

  4. What other opportunities will be happening and how impactful is it if you miss them? Are there conferences, events, etc. that would be opportunities lost if you didn’t attend while you’re planning time away? If so, are there ways you can make your time away a dual experience where you are able to attend the opportunity and make space for time away from the day-to-day work?

When the boss is on vacation, I'm on vacation. (Meme of man pointing at head)

When the boss is on vacation, I’m on vacation.

2. If this image is what you think your team is thinking when you take a vacation then you may need to work on your company culture

Your team should know what their expectations are while you’re away and how you’re going to hold them accountable for these expectations when you return. For examples of how to set up accountability management see my post titled Accountability for All.

The last thing you want to be thinking about while you’re out of the office is if your team is doing their work. If you can’t trust your team to continue without you looking over their shoulder, that’s a reflection of you AND them.

  1. Let people know ahead of time that you’re going to be out. Alert those who directly report to you, and those you report to, any contractors, clients, etc. of your upcoming time away and if you’ll be completely away from all work or available and to what capacity – it’s ok if this varies depending on the different groups of people you’re alerting. If I’m going to be away for an extended period (meaning more than 3-5 business days) I will add a P.S. to my email signature two weeks before I’m out alerting people I’ll be gone, and the dates of when I’ll be out of office. This way in case I forgot to tell anyone they’ll be alerted to this ahead of time.

While You’re Out

Create a plan ahead of time for if a “sh*t hit the fan” moment occurs while you’re away. I tend to get anxious while I’m on vacation if I don’t check my emails. Part of this is because I’ve had a few big things happen while I’ve been on vacation in the past and there’s some PTSD associated with this.

Even if your out-of-office (OOO) message says you won’t be checking your email while you’re away if taking a few minutes to look at what’s in your inbox when you feel like you need to is OK and totally acceptable. I like to go through and clean out any newsletters, mailing lists, or emails that I know won’t need responding to pretty regularly while OOO. I try not to open emails that I know are going to need full attention or follow-ups unless they seem urgent. This helps with keeping the overall inbox number lower too so it doesn’t feel like as much when I return.

Re-Entry to Work

There’s nothing worse than coming back to work feeling refreshed only to have a bunch of stuff dumped on you to then feel like you had no time away.

Having a re-entry plan helps manage this

  1. When are you actually back for customers/clients vs your team? When I take extended time away I usually will tell my team my actual day back but my OOO will have a 1-2 day further date. I do this so that when I return I have a day to go through things, assess what’s been happening while I was away, and also prioritize what needs immediate attention vs other work. I also tend to block off my first few days back from any external meetings.

  2. Give your team members a day or two before you add new items to their plates. Sending an “I’d like to have a check-in to catch you up on what happened while you were away, what works for you?” makes the difference in letting team members feel valued and appreciated.

  3. Respect people’s choice to not share about their time away. Not all vacations are what we typically think of as vacations. There may have been no time lounging around or traveling for pleasure. Sometimes vacations are because of family issues or other personal reasons. Please respect people’s wishes not to talk about their time away in a group or public setting, or judge how they spent their time away.

I cannot say this enough, time away is necessary! We put in way more hours a week in our ventures than we even realize. This applies especially to founders but also to our team members who “punch a clock”. Making space for time away supports the overall success of your venture in a variety of ways, don’t miss out on the opportunity.

Want to talk more about preparing for time away? Or to talk about anything else related to running and working for a startup venture? Schedule an Office Hour with me.


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