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Five Thoughts on Surviving the Holidays as an Entrepreneur (and a Marketer)

For some reason this year it struck me particularly strongly how different the holidays feel when you’re an entrepreneur than they do when you just work for someone else. 

Back in those carefree days, the period leading up to Christmas was a gentle slide into, well, not much work getting done. People brought in treats, silly sweaters were worn, holiday parties were had, white elephant exchanges occurred, and it was generally pretty well expected that nothing important would happen until “the new year”. It was a pleasant way to get in the mood for my Christmas break and a relaxed finish to the year amongst the good cheer of colleagues.

But now (I’m sure you relate), I own my own company, and there is no comfortable slide into the holiday spirit. It’s a little harder to relax into the season when the buck literally stops with you, of course. And for us, as a marketing consultancy with e-commerce businesses among our clientele, the period from September to December is anything but relaxed. Yes, I’m sure some of you relate to that as well.

This all got me thinking about what we can do about that. Because, after all, the good cheer and togetherness that come with the holidays is a wonderful thing for the soul (and your team)—and who wants to suddenly try and switch off from panic and mayhem right before you sit down with your family on the first day of Hannukah or Christmas?

Tips for managing the holidays as an entrepreneur

  1. Remember that you have (some) control over this. Yes, I know you’ve got a lot on your plate—especially if you’re D2C (direct to consumer)—but that doesn’t have to mean that you give into the stress entirely. I know that a lot of the stress I feel during this time is stress I’m bringing on myself by worrying about stuff when I simply don’t need to. Be aware of this, and try and make time to shed some of that unnecessary baggage. 
  2. Do your holiday marketing planning way ahead of time. One of the easiest ways to cut down on stress (and chaos) is to get your planning done as far ahead as you can so you’re not making decisions at the last minute—especially if you’ve got orders flooding in or if you’ve also got a round of social commitments for the season. Get your holiday email schedule planned back in the fall. Plan your digital marketing campaigns as early as you can. And if you’re a B2B (Business to Business) company, get your planning for the new year done early as well!
  3. Execute your holiday marketing campaigns way ahead of time, too. Even better than planning early is having your holiday marketing done early. Embrace scheduling! Get your digital campaigns set up and scheduled well in advance. Get your emails made and scheduled. Get any website updates lined up and ready to go. Need new collateral? Get it made early! 
  4. Hire help with your marketing and more! Sure, this may sound self-serving since we offer the type of help I’m talking about, but it’s good advice anyway. Bringing in a little expert help—whether to set up your holiday email campaigns or to just answer phones—can take a lot of the pressure off. And, because an expert has the experience to get your marketing set up faster and (likely) more effectively than you could, it’s a worthwhile investment on all fronts. And yeah, did I mention it? We can help with the marketing stuff (just not the phones). 
  5. Bring in the cheer. It’s important to make time for that “silly” holiday stuff that helps everyone de-tune at the end of the year. Even as the boss, take the time to participate with your team. Of course, this is a little harder if you have a remote team or are a single shingle, but you can still work up a little cheer. Have a remote holiday happy hour. If you’re a single shingle and you have a membership at a co-working location, make sure to go to their holiday party. Put up decorations. Send holiday cards. Make sure to wish people happy holidays. Consciously make time to enjoy the season.

I hope this helps, even just to remind you that it’s okay to relax and enjoy this time of year. And, of course, we’re always here if you need help doing it. 

We hope you have had, are having, and will have a happy holiday season this year!

Katie & Theron

At Urban Sherpa Marketing Co. we offer fractional marketing director services, which include marketing advisory, strategic planning, program and staff management, and marketing implementation for small to medium businesses and startups. Our goal is to make high-quality marketing possible for every business, no matter the size. Think of us as your outsourced marketing department, strategic marketing adviser, and phone-a-friend marketing lifeline. We specialize in building efficient marketing programs to grow your business without blowing the bank.

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Help! I forgot to plan for holiday marketing! What now?

It’s common marketing knowledge that you should start your holiday season marketing planning as early as August. And if you need to bring in inventory to support it, you should have really started planning right after last year’s holiday season. And common knowledge here is correct – you absolutely should plan early.

But, as with many marketing best practices, starting really early isn’t always realistic for smaller businesses, especially those struggling with their marketing function. (Hey! Need help with that?) It’s pretty common to instead feel like the holiday season is an out of control freight train screaming down on you.

So, what can you do if you’ve gotten this far (early December) without doing, well, anything? Do you have any hope? 

Well, sure.

How to salvage your holiday marketing

1) It may not be too late!

Sure, some crazy-organized people start their Christmas shopping as early as September, but there’s a lot of us that wait until the very last minute. As long as you don’t rely on the already-burdened shipping companies to get products to customers, there’s no reason you can’t throw a last-minute-shopper’s sale right up to the, well, last minute. 

Unlike in the past, when you needed to get your media buys together months in advance, the great thing about digital marketing is you can slap up an ad tomorrow. Or send out an email series to your customer list today. And there’s no time like the present!

2) Celebrate the New Year

Unless your business gets a big chunk of its revenue from holiday gift sales, why not skip the holiday season altogether? Stay with me, here! The thing is, everyone is getting inundated with messaging right now. Inboxes are piling up, catalogs are flooding physical mailboxes, we’re all being followed around the internet with great gift ideas (!) and seasonal deals… basically there is a LOT of competition for attention. 

What about sending out a Happy New Year card to your clients instead of a holiday card? Or putting on a New Year’s Resolution sale? Your message will stand out a lot more in the quiet time after the holiday season  is over than it would in the midst of the fray.

3) Double down on the next holidays

OK, so you didn’t get things together in time for Hanukkah and Christmas gifters. That doesn’t mean you have to slink away with your tail between your legs. Start planning now for your marketing for the next set of holidays. 

Valentine’s day? Sure! Mardi Gras? I don’t know, why not? Mother’s day? Absolutely. Start thinking now about what offers you want to put together, what your messaging will be, and how you will advertise your huge Belly Laugh Day sale. You’ll be well ahead of the pack!

4) Try to relax about it

Our last piece of advice is a bit more metaphysical: try not to worry too much about whether you’re doing your marketing “right”. Sure, the holidays are a great time to generate sales for a lot of businesses, but it’s not the only way to do so. Depending on your industry, it might not even make any sense to pay attention to the holidays at all. Remember that people are super distracted right now, and really don’t need another voice shouting at them. Give yourself a break – you’ve done well to get through the year – and drink a little eggnog to celebrate your lack of holiday marketing. 

And hey, there’s always next year, right?

Happy holidays (and small business marketing),

Katie & Theron