Gifts for Entrepreneurs and Freelancers: What to Buy and Ask For!

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Choosing Christmas presents can be a real source of frustration for some people. What do you ask for? What do you get that person who’s “impossible” to buy for? This short guide to gifts for entrepreneurs and freelancers is designed to help with those dilemmas.

Rather than produce a cynical list of random ideas, I’ve decided to go in a different direction. I’ve looked back over the year at the products and services that I’ve personally bought and been really pleased with. As such, this is a short list of genuine recommendations.

So, whether you’re looking for something for the entrepreneur in your life, or trying to decide what to ask for yourself, hopefully there will be something here to inspire you. (You can always forward this article to somebody complete with a heavy hint!)

Let’s get started.

Music to your Ears?

I begin with something I put in this article last year as well: my beloved Sennheiser wireless headphones. They’re still going strong.

LOTS of people are asking for Apple AirPods this year, to the point there’s even talk of major stock shortages. However, much as I’m a bit of an Apple fanboy, they simply don’t appeal. For a start they’re really expensive, and I just know I’d lose them within a matter of days – probably on the counter of a shop when taking them out to pay!

The design of these makes much more sense: They’re on a neck band so you can take them in and out of your ears without losing them. The Bluetooth pairing always works, the batteries last ages, and – most importantly – they sound great with both music and podcasts. They also serve as a hands-free for your phone. In my experience, people can always hear me, even when I’m walking along a windy beach.

In case you’re wondering why I’m putting these at the top of a list of gifts for entrepreneurs, the reason is simple: podcasts and audiobooks. You can do lots of learning with these – all whilst travelling or getting exercise.

Find these Headphones on Amazon

Print Like a Pro

After 15 years in business, I’ve lost count of how many inkjet printers I’ve been through. They seem to go wrong really easily, the ink dries up, and they’re generally slow and painful to use.

After pondering the environmental impact of binning yet enough hunk of out-of-warranty plastic, my wife and I decided to go for something better. I was staggered how cheaply you can buy a color laser printer nowadays.

This HP model has ticked all the boxes for us. It’s super-simple to set up and configure, and we had it printing from laptops and iPads within minutes. It prints double-sided, which gives it another environmental tick, and the quality is great for everything we need it for.

Yes, it’s more expensive to replace toners compared to inkjet cartridges, but with modest printing requirements you don’t have to think of that too often. I only wish I’d invested in a “real” printer sooner – but then again, this would have cost literally thousands in 2004!

Find this Printer Here

An Office on the Move

Entrepreneurs and freelancers are often based largely at home, but it’s good to be prepared for business trips.

Anybody who goes away for just one or two nights faces a bit of a dilemma as to what to carry. I’ve never really splashed out on quality luggage before, but my Samsonite Mobile Office case is ideal for all my tech stuff, and the necessary toiletries and changes of clothes for a quick trip.

I cannot overstate how much I like using this thing! It’s just incredibly well-thought-out, with a compartment you can get to easily, for pulling out a laptop or passport, and another for clothes. Is saves taking a separate bag and case, and is really easy to move through busy airports and train stations.

When I bought one of these, I actually splashed out a little more on a hard shell version, but can’t find the exact one on Amazon any more. Whichever you get – whether it’s for you or the frequent traveller in your life, I think you’ll be pleased with it.

Find the Samsonite Mobile Office Here

An Inspiring Course

One thing I notice about successful people is that they never stop learning.

It’s easy to be cynical about the number of training courses out there, but the truth is that the people who keep making progress are those who keep learning more and more. I know lots of six-figure-plus bloggers who continually invest in new courses for themselves.


One course I purchased and completed personally this year was Making Sense of Affiliate Marketing from Michelle Schroeder-Gardner (who I also interviewed here). If you, or anybody you care about, wants to get into making money from blogs and websites, this is packed with actionable advice and highly recommended. Even after working in the industry for many years, I picked up plenty of ideas for my own sites.

Find the Course Here

Something for the Experienced Entrepreneur

Any list of gifts for entrepreneurs has to include a book or two. However, I tend to find they almost always concentrate on the startup phase.

On a trip to Amsterdam earlier this year, I was delighted to finally find a book pitched at more experienced entrepreneurs: The Messy Middle by Scott Belsky.

It tackles the kind of subjects you don’t think about in the beginning: taking on the right staff, scaling and preparing a business for sale. It’s great for those who already have a business and are looking to take things to the next level.

Find the Book Here

The Ultimate Tech for Freelancers?

We’re moving into luxury item territory now, but every entrepreneur needs a laptop, and Apple’s latest 16-inch MacBook Pro has been described by most pundits as a fantastic “return to form.”

Apple has had issues with its MacBooks in recent years, especially with problematic keyboards (don’t get me started on that!) However, this is a new design that corrects the keyboard issue and brings a bigger screen and various other enhancements.

It’s a long time since Apple brought out a new laptop to almost universal acclaim. If you’ve been holding back on buying something new, it could finally be time. (Or you could ask a very generous friend or family member…)

Find the Latest MacBook Pro Here

A Nudge in the Right Direction

I’m going to end with a shameless plug for a service of my own!


As you may know, I offer coaching and mentorship to aspiring writers and bloggers. Whether you’d like some personalised guidance yourself, or can think of somebody who would benefit from it, I’d be delighted to arrange it. If you’d like to buy coaching as a gift, I’ll happily provide a voucher for Christmas Day.

I’ve received some fabulous feedback from previous mentees, including one person saying that “the money you spend on Ben will come back to you tenfold.” This could be a great gift if you or somebody you love would like to kick off a new project or career in the new year.

You’ll find the details and prices using the link below – don’t hesitate to get in touch if you want to ask any questions about this.

Find out About Coaching and Mentorship Here

Not Found Anything you Like?

If you’re still lacking inspiration, Amazon has a whole host of other related gift ideas here.

Whether you’re buying for yourself or other people, I hope Christmas brings you lots of surprises and inspiration 🙂

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