The Entrepreneur’s Guide to the Holidays

Balance. It’s a buzzy word. But for many entrepreneurs, the mere thought of balance during the holiday season is stressful in and of itself. Running a business is crazy enough without also striving to see family, cook treats, wrangle parties and oh, make merry.

As I talked to entrepreneurs and small business owners, one theme came up again and again: figuring out what you want out of the holidays is the first step to making the season great. Whether that’s a week straight of not answering email, more time with your children, cocktail parties with friends and colleagues or simply enjoying the once-a-year moments instead of staring at a laptop — start from what you actually want.

For example, what my husband/co-founder and I wanted last holiday season is very different than this year. Last year, our company was in a high-growth (and very exciting) stage, and I also knew I’d be traveling on a book tour for the first three weeks of December. All I wanted for Christmas was to see my parents and siblings for three days and do nothing — nothing — before heading into a January sprint. My husband wanted the exact same thing, so we prioritized seeing our respective families and spent the holiday on opposite sides of the country.

This year, we’re at a different stage and want something else out of the holiday season: a chance to go on real, week-long vacation together and leave the laptops at home. So we’ll front-end a lot of work in early December and peace out for the latter half of the month. And next year, who knows, we might want to be all nostalgic and ski and bake cookies and actually put up decorations. But as an entrepreneur, it’s your prerogative to pick and choose what parts of the holiday season to focus on.

Once you define what your dream holiday season is, read on for tips from other entrepreneurs on how to attain your balance this season.

[Editor’s note: This was originally published November 12th 2014.]

Who Doesn’t Want Balance?

Who Doesn’t Want Balance?

Balance. It’s a buzzy word. But for many entrepreneurs, the mere thought of balance during the holiday season is stressful in and of itself. Running a business is crazy enough without also striving to see family, cook treats, wrangle parties and oh, make merry.

As I talked to entrepreneurs and small business owners, one theme came up again and again: figuring out what you want out of the holidays is the first step to making the season great. Whether that’s a week straight of not answering email, more time with your children, cocktail parties with friends and colleagues or simply enjoying the once-a-year moments instead of staring at a laptop — start from what you actually want.

For example, what my husband/co-founder and I wanted last holiday season is very different than this year. Last year, our company was in a high-growth (and very exciting) stage, and I also knew I’d be traveling on a book tour for the first three weeks of December. All I wanted for Christmas was to see my parents and siblings for three days and do nothing — nothing — before heading into a January sprint. My husband wanted the exact same thing, so we prioritized seeing our respective families and spent the holiday on opposite sides of the country.

This year, we’re at a different stage and want something else out of the holiday season: a chance to go on real, week-long vacation together and leave the laptops at home. So we’ll front-end a lot of work in early December and peace out for the latter half of the month. And next year, who knows, we might want to be all nostalgic and ski and bake cookies and actually put up decorations. But as an entrepreneur, it’s your prerogative to pick and choose what parts of the holiday season to focus on.

Once you define what your dream holiday season is, read on for tips from other entrepreneurs on how to attain your balance this season.

[Editor’s note: This was originally published November 12th 2014.]

Set Expectations for Yourself and Others

Set Expectations for Yourself and Others

After you know what you want for the holiday season — in business and life — it helps to set expectations for yourself and others.

Deborah Grayson Riegel, CEO and Chief Communication Coach of Talk Support, sums it up perfectly: “The single best thing that I do personally and professionally between Thanksgiving and New Years is deliberately lower my expectations for 80 percent of my work and life — and raise my expectations for the other 20 percent.

I lower my expectations on: actually getting meetings scheduled; winning/closing new business for this year; getting other people to focus on my interests and priorities; getting people to focus at all; weight loss (oh hell, weight maintenance); free/discretionary time; feeling pulled in multiple directions.

And I raise my expectations on: strategic thinking and planning for the next year; goal-setting; invoicing and collections; networking; outreach/connections; fun and celebration.

Riegel organizes her calendar and mindset around these areas, and has adopted a winning phrase to keep her priorities in focus whenever a new idea comes up: “Sounds like something we should pick up again in January! Shall we schedule that now so we don’t forget about it?”

Carrie Mantha, the CEO of Indira Collection, goes a step further and also lets family and friends know what to expect. She sends out a pre-holiday update on her life and her startup that concludes by saying:

“I pour my heart and soul into my company almost every day of the year, and I appreciate all of your support so much. I apologize in advance if I have to step away from the festivities to help a customer, and I look forward to stepping out of my bubble and talking about all kinds of exciting things that are *not* my company.”

Plan to Disconnect

Plan to Disconnect

How much — and for how long — do you want to “unplug” from the day-to-day moments of running your business? Knowing what your personal comfort level is will help you prepare, and make the most of whatever moments you do step away. For example, you probably fall somewhere along this spectrum:

1. I can relax fully when I can work for a few hours each day.

Gesche Wai-Yi Haas, founder of Dreamers // Doers, admits to something that many entrepreneurs probably resonate with: “The biggest source of stress for me is actually the forced downtime. While I enjoy just being with my family for the holidays, I get absurdly unsettled several hours into it and want to work a bit. I used to get upset at myself for not being able to completely stop thinking about work — but now I just accept it. My compromise is to enjoy a few hours with my family and then layer in an hour of productive time here and there. This way I am truly present when I am with my family.”

2. I like to take a few days completely off here and there.

Micah Clasper-Torch, Co-founder and CEO of CityBird, has found that this is the technique that works for her. “During the holiday season I like to designate days as being completely ‘on’ or completely ‘off.’  It’s when I try to mix a little work with a little down time that I don’t do either effectively. For instance I might decide, next Saturday I’m totally off, and Thanksgiving, but say Sunday I’ll leave it open to do some work. When I’m scheduling days, I make a to-do list with both my personal and professional “to-do’s” — it reminds me of their equal importance in my life.”

3. I want to completely unplug!

This is how I operate — but there’s a right way to step (almost) completely off the grid. Set up systems and processes in your business so that you can leave things in the hands of an empowered point person — someone who has authority and can take care of anything that comes up. For peace of mind, make an “emergency email” that your key contacts and “screener” can use to reach you if absolutely necessary. That way you don’t have to check your regular inbox and get drawn back into the day-to-day business thoughts.

Find Your Slow Periods and Use Them

Find Your Slow Periods and Use Them

If you’ve ever worked at a corporate job and didn’t take vacation during the week between Christmas and New Year’s or the day after Thanksgiving, you know what I mean: Sometimes, it’s just sloooow. If that time exists — at all — for your industry, find and utilize it.

For example, my company guesterly is in the event space, and customers place orders a few weeks before their event. But there generally aren’t a lot of events during the first two weeks of January. (Seriously, can you think of one? Everyone’s recovering and staying close to home.) So after our New Year’s orders go out the door around December 10th, we’re relatively quiet. That’s the data I used to schedule a few weeks of vacation during December.

On the other hand, December might be your busy season. Sarah Carson, the Founder and CEO of Leota, has found a solution that at least gets her home for the holidays: cloud-based everything. “In the women’s apparel business, there is no ‘slow season.’ We’re constantly designing, manufacturing and shipping. During the holidays, I’m particularly glad our systems are cloud-based so we can work from anywhere. Our company phones can ring on our cell phones; our enterprise technology platform can be accessed on our laptops. For example, my logistics team can be fielding Nordstrom orders and managing the warehouse from home.”

Even though her workflow doesn’t slow down, Carson does make one concession to create her own slow season: “Over the holidays I’m fine with moving into more of a reactive mode where we’re just responding to what’s coming in rather than pushing everyone to proactively chase business.”

Don’t Forget to Celebrate at Work!

Don’t Forget to Celebrate at Work!

With all of the stress of “having a life” outside of your business — and of course, the ongoing demands of actually running said business — don’t forget to celebrate the people who are in the trenches with you. And for the business owner on a budget, a shindig doesn’t have to break the bank. “Last year I hosted a holiday dinner and gift swap at my apartment for the team,” says Julie Sygiel, the CEO of Dear Kate. “We bought ingredients to make pasta for dinner and cooked together so it was fun, and wasn’t too expensive.” At guesterly, it was homemade gnocchi and inexpensive red wine to kick off the holiday season and bond with our team.

No matter how you approach it, spend a few minutes now to schedule a holiday event for your team. Like the rest of your holiday strategy, it’s sure to pay dividends in the new year.

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Make Room for Family Commitments

Make Room for Family Commitments

Nika Stewart, the CEO of Ghost Tweeting, lets her team know that she’ll be relying on them more during the holidays so she can focus on the increased social and family events on her calendar. “We help companies with their social media marketing, and the last thing you want to do during the holidays is let up: For example, I know that I need to post 10 to 20 times a day, even in December. But being the CEO doesn’t mean I have to do it all.”

“Instead, I’ve planned it so that when I can’t give personal attention to my social media, my team takes over things I typically do myself. This way, my marketing is always consistent, and I (my company) appear to always be accessible (even though I am actually out hosting my daughter’s school holiday party, or shopping for gifts.”

This strategy works even better when it’s win-win: Stewart’s employees are paid by the project, so when their tasks increase, so do their paychecks — something that’s deeply appreciated during the season of gift giving.