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People Who Never Break From Work on How to Shake Off the Holiday Rust

CEOs and workaholics offer their best tips and tricks for settling back into the routine when it's feeling overwhelming

Matt Ross is the COO of two companies: RIZKNOWS, a tech-sales website, and the Slumber Yard, a mattress-review site. This holiday break, he traveled to Southeast Asia, but he planned to be back by Friday so he could go into the office to get some work done before work. In fact, he often finds himself at the office the weekend following a long vacation so he’s ready to “hit the ground running” on Monday.

“Yes, it might take a day off your vacation,” he says, “but you’ll be thankful when you feel organized and fresh on Monday when you head in to work.”  

So begins the yearly American tradition of coming back from one of the very few extended breaks most people take from work. Many of us spent it anxious and complaining about not working over our holiday.

Endless work is a tradition that often confuses laborers across the pond: According to the Economist, in the average year, “the average American works 100 more hours than a Briton, 300 more than a French employee and 400 more hours than a German.”

So how should Americans “shake off the rust” from an exhausting three to five days of holiday? Some people I spoke with — executives who work up to 80 hours a week — say the only way to avoid fatigue is to simply never stop. (Welcome to your capitalist dystopia!) But they also gave me some tips and tricks for settling back into the routine when it feels overwhelming.

1. Fly Back Early

Matt Ross, COO of RIZKNOWS and the Slumber Yard:
My company operates multiple internet properties, including popular websites, YouTube channels [and] a mobile application, and employs 10 individuals.

I typically work 70 to 80 hours per week and rarely take time off throughout the year. However, to decompress, I usually plan a big trip over Christmas/New Years when things start to slow down. This year, I’m taking a two-week trip to Thailand and Vietnam.

It’s always very difficult for me to get back into the swing of things after I return from these trips, but I’ve picked up a few tips and tricks over the years to help with the transition process. First, I make considerable efforts to prep for my trip. That includes preparing employees for my absence, making sure payroll is correctly automated for the period I’m gone and alerting important customers in case they need something. I also set up a detailed to-do and reminder list for my business partner to make sure everything runs smoothly while I’m gone.

Perhaps more importantly, I purposely arrange to come back from my trip a day early. So instead of flying back on a Sunday and then heading into the office first thing Monday to get caught up, I instead fly back on Saturday and use Sunday as my catch-up day. I usually go into the office on Sunday for about three to four hours to catch up on emails and address any issues that surfaced during my absence. That way, when Monday rolls around, I’m already caught up and I’m ready to hit the ground running. I’d definitely recommend others try this approach as well. Yes, it might take a day off your vacation but you’ll be thankful when you feel organized and fresh on Monday when you head in to work.

2. Schedule a Business Brunch and Vent About It

Ketan Kapoor, CEO and Co-founder of Mettl, an HR Technology Company:
Getting back to work after a few days can look and be daunting. You feel like you had been enjoying just a few hours back and now you are back to work and on the brink of a routine life — you reminisce a lot and feel a sense of overwhelm and anxiety take over about the pile of work awaiting you.

To get back in the groove in the best possible way is to have a casual brunch meeting with colleagues on the first day of reopening. Just sit back, have brunch and discuss exactly how you feel — how the holidays have been and how getting back to work looks difficult. A casual talk infuses a lot of motivation and makes it seem an easy climb to complex and business-impacting tasks. The rest of the day can be taken to plan for the next day and consequent days and planning accordingly to take smaller and easy tasks first, which will pave the way for bigger responsibilities.

3. Postpone Your Meetings — and Set Your Bedtime Back Early

Carol Archebelle, Digital Media Manager, Foundations Wellness Center:
It’s not necessarily the work itself that is hard to come back to, it’s getting back into the routine. So, for a few nights before I go back to work, I’ll go to bed earlier and get up at the time I’ll need to when I return to work.

I also allow myself to ease back into the routine by not scheduling important meetings on those first few days back. So that I don’t feel “under the gun” when coming back to work, I have anything that deadlines on those first few days completed before I leave for the holiday. Sometimes I will treat myself with a Starbucks coffee, for instance, to get me excited to return to work in the morning. Or, I’ll schedule a fun lunch to look forward to that breaks up the workday. Normally, I’d work straight through lunch but for the first few days it’s nice to have that break.

4. Avoiding Email Is Overrated

John Crossman, CEO, Crossman & Company:
I work 60 to 80 hours a week, and I find it hard to turn off. I know I should do it more often, but even on vacation I find myself working one to two hours a day. It may just be pounding through emails for 15 minutes, but it actually helps me to relax more on my trip.

Ideally, I would come back from vacation on Friday and slip into the office briefly and then knock out some work over the weekend before Monday, but it usually happens that I put in four hours of work on my last day of vacation so I can start to ramp back into things.

5. Make a List for Your Future Self

Blair Koch, CEO, the Alternative Board:
I make sure to take a long weekend every quarter. It really helps keep me fresh and focused. That way I don’t feel like I am grinding away at things, but before a longer holiday comes around, I make a list of actions to follow up on when I get back, with detailed comments: what was the status of every task, who is supposed to do what and by when, what is my next step, etc. The more commentary, the better.  

When I get back, I go back to the list I left for myself before my holiday started. I block off the first couple of hours in the morning I return to get caught up and review the list before even checking emails — because as I go through the emails, I’m likely to find the answers, status updates, etc. to many of the items.

Knowing what I’m going to be returning to goes a long way in helping me let go and enjoy my time off, and when it starts coming to an end, I am more than ready to get back to work. I am excited and ready. Often, I will have come up with new ideas without trying (because my mind is free and clear).

I also make sure to reach out to my team and have a social conversation about their holiday. Just a catch-up to reconnect, etc. By the end of the first day back, if not sooner, I am back in full swing.

Stacy Caprio, Founder of Growth Marketing:
I work six days a week, only taking Saturday off, and usually take specific holiday days off or days for medical reasons. Even when taking days off I like to do small things and check on stats, but on longer holidays where no one else is working, I’ll get back into the swing of things by making a daily to-do list for the first week back so I know exactly what I need to accomplish for each day, in order, including lunch and food breaks, and then use that to guide me for my first few days back.