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Everyone has a small business owner in their life. It could be a solopreneur (they used to be called “freelancers”) or any of the countless Mom & Pop shops we rely on. Whatever the business of the shop –  salon, subcontractor, café or beyond – all small business owners have a few things in common:The never-ending pressure of meeting customers’ demands and payroll. Stress. Being a jack-of-all-trades. Constantly adapting to the changing circumstances under which they must work.

This is all great news for the gift giver to a small business owner. There are lots of opportunities to give a great, useful gift. Here are ten great holiday gifts ideas. Customize according to the personality and business of the recipient.


Don’t buy them the actual tools of their trade. People tend to be particular about that sort of thing. Even so, there a ton of great business tools out there that will help them out.

  1. Annual subscription to a fantastic, much needed online tool.

This could be a conferencing software, customer management system, accounting software, HR systems, just as an example. Small business owners waste a lot of their time and money trying to manage functions they don’t have to. Instead, they can use a software-as-a-service (SaaS) tool that provides both efficiency and expertise.

These cloud-based tools are the great equalizers for small businesses. This gift works best if you know the owner and their business well.

  1. Manual or digital notebook.

Entrepreneurs are by definition, idea people. The ideas always come and go. If they don’t have a way to get them down, the ideas are lost. Small business owners also seem to have a constantly shifting list of to-dos.  So notebooks are useful.

There are digital options, like Evernote and Trello. Get them the premium versions; don’t just sign them up for the free versions. A lot of the digital notebooks now work with voice recording notes for the business owner who use their phones to record their random thoughts rather than write them down.

For people who still prefer pen and paper, you can choose from a variety of notebooks from high-end, leather bound portfolios to the more pocket-friendly Field Notes.  Some tools are crossing the digital/manual divide, like Evernote’s integration with Moleskine.

  1. Replace a critical piece of office furniture or equipment.

How old is their office printer or storage cabinet? How much would they love an ergonomic desk chair? Small business owners are notorious for neglecting their needs in the business. You’d be surprised what a difference a comfortable desk chair can make to their daily energy.

  1. Backup chargers.

For the small business owner who’s never in, or doesn’t have an office.  Instead of a desk chair, what they need is a constantly charged phone and laptop to stay connected. There are portable battery packs and chargers, including bags and wallets that charge phones.

Whether it’s needed for meetings, to post announcements or changing schedules, a whiteboard serves whatever community messaging need a specific small business team has.

A good add-on here is a small whiteboard for the small owner to use on their desk. Some business owners still like work things out by hand, either a to-do list or quick calculations, but don’t want to waste paper. Having a small white board they can write on instead is something they won’t think of themselves, but really appreciate once they have it.

  1. Great entrepreneur or business book.

A successful entrepreneur is constantly learning. Buy your small business owner a few business-related books. They can be related to their industry or more general business growth books. Here’s a good list of “Books Every Small Business Owner Should Read” to give you some ideas. You might also want to consider a biography or autobiography of a business person they admire.

Instead of a book, you could get them a subscription to a business or industry publication that would be valuable for their business.

  1. Branded giveaways.

You can literally put a business logo on anything today. Literally. Help your small business owner out by buying some branded giveaways they use. Do they own a salon? How about branded compact mirrors? A medical practice could giveaway branded pill boxes. Really. You can a business logo on anything.

For them, these branded giveaways are great marketing and a great reminder of your support.  Like signing them up with a SaaS subscription (idea #1), this option works best if you know the small business owner and their business well. Since you’ll need their logo art to make the purchase, this is a gift you’ll talk about with them before buying anything.


These last few gift ideas are a bit more personal, but also give your small business owner great support in their business.

  1. Bespoke clothes.

Everyone has a uniform. Some small business owners regularly must wear full professional dress. Others can dress more casually or are often in work clothes. Whatever the uniform, having custom fit clothing always raises their game.

Let’s thank the internet again. It’s made bespoke clothing available for very reasonable rates. Men’s shirt maker, Original Stitch, will produce casual or formal dress shirts for less than $100. Sumissura is a similar bespoke service for women’s clothing.

These options can be especially good for the small business owner who doesn’t normally need to dress formally, but wants to show a smart professional side when required.

  1. An awesome experience that requires they take a day off.

Give the gift of time. Spa days or tickets to an exciting sports event are usually good bets. You can get more creative with services like Great American Days, which is a service that can arrange experiences like bungee jumping or driving a race car around the track.

  1. Make them a hero boss.

Give them a gift to they can give to their team. Cater a great lunch. Buy an experience for the team. Bring in a massage therapist for a day.

Hopefully you’ve already figured out which way you want to go. You can find gift options off this list from $20 to $500. Whatever is appropriate for you to spend for a given small business owner, there’s a great small business owner gift that they’ll genuinely appreciate.

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