How to Survive the Holiday Scene As an Entrepreneur

If you’re an entrepreneur as many thirtysomeones are these days [it’s a GenX/Millennial thing…]), you’re always ready to talk about your new project and share it with the whole world. Maybe the holidays seem like a perfect time to practice your pitch on family and friends, tell people about what you’re doing and get the word out.

But there is a delicate balance we as entrepreneurs and business owners have to consider. Sure, we’re excited to talk about everything we’re doing and how our great ideas can help so many people, but we also have to remember that family gatherings may not be the best place for doing business. Here are a few traps to look out for this season and some tips I’ve developed over the years to keep the balance and not end up with egg…nog on your face.

Mingling Question #1: What do you do?

There’s really nothing worse than listening to someone ramble on and on about his or her latest venture to end up on the other side not knowing what the person is talking about and wondering where the last 10 minutes of your life went. Sure, for most people, their job title says it all. ‘Lawyer,’ ‘Manager’, ‘Baker,’ all crystal clear. But ‘Entrepreneur’ needs some explanation and expansion.

What kind of entrepreneur? What do you do all day? How do you actually make money?

So where do you start to answer so you don’t end up on a roller-coaster of explanations and examples that go nowhere fast?

I’ll pass on some great advice I got from another coach, Christian Mickelsen. He says to do away with the titles altogether. For example, if you design software I’m sure you know by now that the average Joe has no idea how you do what you do. Instead of ‘Software Designer’ you could say, ‘I develop computer programs and programming to help people do their taxes themselves from their home computer.’ Instead of ‘Coach’ I’ve been practising saying that, ‘I listen to the common concerns of thirtysomethings and lead them to solutions that will help them achieve their goals and live a more abundant life.’

This is even good advice for non-entrepreneurs because it makes your job more understandable and relatable. Even as a Baker you can mention your specialties or holiday favourites: ‘I’m a baker who specializes in vegan and gluten-free yule logs this time of year’. As a lawyer you can talk about your ideal clients and who you really like working with. For more examples, see Christian’s full post HERE.

We’ve all been faced with the guy who’s a ‘Data-reconfigure analysis statistician something or other for a multi-national logistics something something corporation’. We try to keep an interested face but sometimes the egg nog starts to kick in and there’s no hope. On a more personal note, I was recently baffled when I was introduced to a ‘Solutions Integrator’. Instantly, a load of self-doubt for not knowing what this was arose and an awkwardness settled on the conversation because I was too embarrassed to ask for clarification. All of which could have been avoided by him simply saying first-off that he ‘sources technology and programs to make his company run more smoothly.’ Ahhhhh… the simplicity…

Basically, the holidays are no time for extra thinking. Be a doll and take the guess work out of it for your relatives and they’ll not only be thankful but probably more interested in what you ‘do’ rather than being confused by your title.

Mingling Question #2: What have you been up to?

For entrepreneurs and free spirits that may be nearer to the beginning of their journey, this question can be as nerve-wracking as taking your driver’s license test in the middle of a snowstorm. You can’t see, your palms are sweaty and you’re not thinking if but when you’ll swerve off the road.

Sometimes at the beginning of a venture, the idea is there but articulating it might be a danger zone. Just because you understand it and have the vision, doesn’t mean everyone is going to get it. So consider these options:

  1. Don’t mention the project. This could seem like a cop out or a middle finger to the Law of Attraction, but it could also be a way to protect your idea from scrutiny in its incubation period. However, this isn’t the advice for someone who has an idea that is ready for sharing. I’ve also seen entrepreneurs shy away from sharing their ideas in fear that they’ll be stolen. Trust me when I say, nobody can steal your idea. Even if they had your basic elevator speech memorized, they couldn’t put your unique spin on it. Plus, contrary to your sceptical mind’s beliefs, not everyone goes to holiday parties for a great place to find the next best thing.
  2. Mention the project. But practice first. If you think you’re ready to reveal your plans then go for it. Do some research on effective elevator pitches so you get to the point. Practice your pitch so it sounds natural, but convincing.  And, own the complements that come your way for being so brave and going out on your own. Check out one of my favourite videos on nailing your introduction HERE.

Pitching to ‘The Fam’

It’s great to let your family in on what you’re doing, but it could be best to allow it to happen naturally. If you decide to not mention much but there are still a lot of questions, answer them as honestly as possible (Santa’s watching you know…). Also, keep in mind you could also say that there’s going to be an opportunity for them to hear more about it when you officially launch.

The launch is where you can do this with full transparency. I recently had a Christmas dinner at my house and told a few guests to arrive early to be my guinea pigs for a practice launch of a new business I’m starting. I didn’t surprise them with it and hold them hostage, I said come early to support me on my new venture if they could. Luckily, they were very supportive. I talked for about an hour, letting them in on all I’ve been doing and how they can support me if they like. Then, after all questions seemed to have been asked, we let it die and dinner got started. It’s important to not only drop the subject but allow people to feel comfortable after a presentation by making it clear that there’s no pressure to invest or buy, just to be open-minded, listen and then move on.

Finally, if you are worried about what ‘The Fam’ will think this holiday season as you reveal your new ventures and projects, go in with a little preparation and awareness for what you are ready to put out there. Just because it’s the holidays doesn’t mean your project knows that – it may not be the right time. There will always be another chance to reveal your project on your terms. But do plan ahead. They will ask, and that’s a wonderful thing too because it means they care. Awwww….

Have a wonderful holiday season to all you thirtysomeones out there with budding new projects. I’d love to be YOUR guinea pig if you like – Practice your pitch in the comments below! Or get in touch at for more success tips and advice!