Holidays Gigs: A Portal to Defensive Entrepreneurship

On the most wonderful time of the year for starting a cushion

If your radio station has yet to unleash the holiday tunes, let me be the one to remind you that it’s that time again. The most wonderful time of the year for banking easy extra cash. If you have a particular set of skills and a particular need and motivation for some bonus money this time of year, read on. You have skills and needs. Others have needs and cash. My gut tells me that after a muted, pandemic-soaked December 2020, folks are going to amp up the festivities this year, maybe even get a bit spendy.

But, I interrupt this broadcast to give you a bigger picture on what November and December can mean. If you’ve read some of my other pieces, you may know I’m a fan of defensive entrepreneurship, having a structure in place so that you always have a Plan B, C, and D to fall back on. Even an income-generating plan you could start tomorrow if you had to.

I’m going to give a run down here of five broad areas of holiday-season services you can consider offering others in the coming months to bring in your own glad tidings. Before that, I ask you to consider how any holiday gigs you pursue can do double duty. Don’t just make some extra cash, use the opportunity of these seasonal services to get your own defensive entrepreneurship plan off the ground. It’s an excellent jump-start on a New Year’s resolution you won’t regret.


Here are the 10 points from my strategic defensive entrepreneurship checklist and how they may relate to holiday gigs. Refer here for greater detail on each.

  • Cushion — Can you use this holiday money to bolster your cushions of savings and/or needed insurance?

  • Day 1 Go-To — What’s your Day 1 Go-To for the holidays? Maybe it’s offering decorating, gift-wrapping, child care, or accountability coaching services on Facebook. Maybe it’s posting on LinkedIn about the availability of your string quartet for elegant gatherings or your ability to pen persuasive end-of-the-year appeals letters for nonprofits.

  • Internal Strengths — Among other things, draw on your creativity (what all is possible?) and a sense of service (how can I help?) in crafting seasonal offerings.

  • Network — Make connections, renew connections, share connections. Take advantage of a social and benevolent time of year to commune and communicate with others.

  • Lifestyle Matters — During this reflective time of year, consider what matters to you and think through alternatives for unexpected scenarios. You’ll build real options and psychological resilience.

  • Skills — Take note of the skills that are easiest for you to market in November and December. Does this help you think about how you can promote them going forward?

  • Freelance — What are your freelance options? Meeting others’ end-of-the-year needs is a great way to test the waters and show others what you’re capable of.

  • Microbusiness — Similarly, is there a little business — even the skeleton of an idea — you’ve always wondered about for yourself? Now may be the time to try it very small scale with minimal up-front resources or commitment required.

  • Action Plan — When you find yourself in front of a crackling fire with feet up, cocktail in hand (or other cozy environment), ruminate on a defensive action plan for various area of your life. Start a plan mentally when the stakes are low and you’re feeling warm and fuzzy.

  • The AWE Question — And, while you’re at it, ask yourself: And What Else? Is there anything I else I need to feel safe and secure in life? A layer of financial, social, physical, of psychological protection I can put into place in the coming year?


Decorating and Household Services

  • Holiday window displays for business storefronts — Here’s more inspiration and advice on working with small businesses.

  • Hanging outdoor lights and seasonal displays

  • Indoor holiday decorating and tree trimming

  • Deep home cleaning for the season/end of the year

  • Pet and plant care while others are traveling

And What Else? Use the easy entrée of holiday needs to show off your abilities and that you can easily extend to similar lawn, home, care, and decorating services throughout the year.


Gifts and Cards

  • Addressing envelopes — Bring your calligraphy or legible handwriting skills to other people’s mail.

  • Custom-designed or handmade cards for families and businesses to give out

  • Research and shopping for unique gifts

  • Gift wrapping and gift delivery

  • Standing in line to mail packages at the post office — Hire yourself out as a seasonal holiday assistant and do all the things.

And What Else? Use products to test the waters on Etsy, Ebay, or your own e-commerce site. Use services to launch yourself year-round in area like crafting and design, event planning and support, and personal/virtual assistance.



  • Baking cookies and other festive treats

  • Providing music for public events and private parties — soloists, ensembles, DJ, singer/s

  • Singing telegrams with gift/floral deliveries

  • Bartending/hosting/food prep/food service/security for private and company parties

  • Party planning, party shopping, navigating CostCo crowds

  • Covid patrol — Make and sell holiday-themed face masks. Be the designated Covid patrol for a private function or company party, the person who keeps windows open and fans running, who reminds guests about mask wearing and social distancing so the hosts don’t have to.

  • Goodie bags for party favors— Can you source original items then assemble them with yuletide artistry?

And What Else? Use the ease and ubiquity of holiday parties to smooth your way into regular entertaining gigs or a related microbusiness.



  • Writing and sending customized letters from Santa

  • Child care — Charge a premium for December weekends.

  • Child care with seasonal fun — Offer a package that involves baking cookies, making homemade gifts, and hot cocoa while watching holiday classics.

  • Santa at the mall — Take other people’s kids, get photos, hear the scoop on what they want from Ole St. Nick.

  • Holiday peeping — Take other people’s kids to look at holiday decorations when their parents need them out of the house for a few strategic hours.

  • Santa on call — Be the jolly old man or Mrs. Claus for private events or corporate shindigs; get creative and get paid for making quick appearances at windows, dashing through backyards, sneaking through alleys ringing sleigh bells…

And What Else? Use the special kid and child care needs of the holiday season to spark ongoing creative offerings for kids and families. (And, here are other ways to think about gigs around kids, i.e., your kids and their wild and woolly schedules.)


Coaching, Writing, and Other Professional Services

  • Writing — family holiday letters, end-of-year appeals for nonprofits, end-of-year business communications, holiday-themed business newsletters

  • Coaching — health and wellness accountability during the holidays, headstarts on New Year’s resolutions, relationship or conflict coaching for fraught or complex family situations

  • Support — any manner of emotional, social, or logistical support for holiday blues or end-of-the-year schedule crazies

And What Else? Use your most useful professional and support skills end-of-year to leave a magical impression on your clients. Most of us can use a helping hand in one department or another during the holidays and may be a bit more open to being touched by your angelic presence too.


In summary

  • The holidays are the most wonderful time of the year to make some easy extra cash.

  • Use this as an opening to also learn about the cushions of defensive entrepreneurship and begin putting a plan B, C, and D into place for yourself.

  • Review five different areas where others need seasonal help: decorating and household services; gifts and cards; entertaining; kids; coaching, writing, and other professional and support services.

  • Use gigs and parties for appropriate networking. Ask satisfied customers for referrals. Tell satisfied customers what else you can help with throughout the year.

  • Keep track of your satisfied customers and notify them next October about your availability.

  • If you get too busy, receive too many requests, all the better. Pass on the work to a friend and collect a commission or finder’s fee.

  • Always ask, And what else?, to make sure you’re putting enough financial, psychological, physical, emotional, and other cushions in place so that you can go through life with security, comfort, and options.