How To Navigate Awkward Holiday Gatherings As An Entrepreneur

Holiday gatherings mean being asked the inevitable question, So, what are you doing for work these days?

Every entrepreneur knows that this question really means something along the lines of, How do you afford to live?

I really wish that we could change the conversation to, So, what are you most passionate about these days? After all, the main reason we strike out on our own is to give more of our time to the projects and the people we love—you know, the people gently interrogating us over a maple-glazed spiral ham.

As entrepreneurs, we are constantly thinking about how best to represent ourselves. At networking events, we are poised with a perfectly tailored elevator pitch. When a client calls with a question or issue, we assist them with complete composure.

But who has the energy to be on when you’re sitting next to Aunt Ann at an overcrowded dinner table and all you really want is for her to please pass the salt? So, you smile, cobble together a semi-coherent response, and reciprocate with some variation of, What’s new with you? before she has a chance to weigh in on your unconventional life choices too heavily.

That was last year. This year will be different. This year, you will be ready, because you know the secrets to surviving awkward conversations.

In fact, not only will you be able to endure your holiday gatherings, you’ll leave your distant relatives in awe of your competence and passion.

All you need to do is keep the following tips in mind.


4 Tips to Navigate Awkward Conversations as an Entrepreneur (at the Holidays, or Anytime)


1. Take yourself seriously.

As a freelance writer and entrepreneur, I find myself constantly justifying how I spend my time (I do a lot of reading and ruminating before setting down words). When asked So, what are you doing these days? I used to respond in one of two ways:

  1. I would launch into an overly complex explanation of my long-term personal, creative, and professional goals, and end up sounding pretty unsure and unorganized. Or,
  2. I would immediately delve into one very specific facet of my writing or business, usually whatever was most lucrative at the time, because I assumed that’s what people wanted most to hear.

Here’s the thing: In order for other people to take you seriously, you need to take yourself seriously. This is especially true when it comes to family. Your family has been there through every single one of your life phases. Once upon a time, I wanted to be a geologist because I “discovered” a bunch of geodes in my backyard. (To this day, my mom will not admit that she staged them.)

Show your family that this is not just another phase to be outgrown. Believe that you are in the right place, doing what you need to be doing. Entrepreneurship is a completely valid trajectory. What matters most is that you’re passionate about what you’re doing and deliberate in its execution.

Focus on how you see yourself and how you want others to see you, rather than how you spend your time or your current financial situation. Speak about the amazing opportunities you’re creating for yourself, the inspiring projects that you’re working on, and your goals for your new business. Speak with conviction.

If you take yourself seriously, others will, too.

2. Keep your answer clear and concise.

Speaking clearly and simply inspires confidence. Whether you identify as a writer, restaurateur, or eCommerce mogul, people will believe you if you avoid jargon and keep things simple.

When asked this inevitable question, I now simply respond by saying, “I am a writer.” Sometimes, I go one small step further to say that “I have my own business writing grant proposals, articles, and branded web content.”

Whatever your industry, you might simply reply, “I run my own business” or “I’m starting my own business.”

This abruptness—while still being clear—leaves a bit of mystery and intrigue. Naturally, people will want to ask follow-up questions. That brings me to next last concept…


3. Be prepared for follow-up questions.

Most likely, people will be completely interested in the way you categorize your particular brand of entrepreneurship. Then come the follow-up questions.

What kind of grants/articles/content do you write? is a natural follow-up question for me and one that I encounter often. I’ve honed a response that encompasses all these areas as concisely as possible.

I explain my areas of expertise (non-profits, branding, public relations, social media, literature) and that I’m in the process of co-founding a boutique communications company.

All while sticking to a fiction writing schedule—because my novel isn’t going to write itself.

Follow-up questions demonstrate genuine interest, so don’t get defensive. Now is the time to elaborate. Keep the first two tips in mind as you do. Don’t overwhelm your audience with terminology. Leave some space for additional follow-up questions, and let the conversation flow steadily and naturally.


4. Be a solution to a problem.

Another way to approach the topic of “What do you actually do?” is to focus on how your work translates into value for your customers or clients.

Begin with the problem you’re solving. Then explain how your business helps solve that problem.

For example, I might begin by saying, “It’s hard for at-risk youth to find gainful employment. I write grant proposals that help nonprofit organizations provide them training and support.”

This is a much more compelling way to explain the grant-writing aspect of my business, rather than belaboring my process and deadlines.

The problem-solution format can be useful, because what’s obvious to you may not be obvious to your audience. And beyond that, people have short attention spans. So, don’t wait or hedge—get right to the interesting and relevant details.


Practice Makes Perfect

Holiday gatherings can be stressful.

By streamlining how you present yourself to your family, you’ll create an improved sense of confidence that will ultimately benefit your overall goals—because let’s be honest, our family can be our toughest critics, so if you can represent yourself well to them, you can represent yourself well to pretty much anyone.

Here’s hoping you parry the awkward questions and have holidays filled with joy, love, and relaxation. If this article was helpful to you, or if you have some additional advice you’d like to share, please let me know in the comments!


Courtney Landi
Courtney grew up in NY’s Hudson Valley and currently resides in Greater Boston. She has a background in public relations, received her MFA in Writing from the University of New Hampshire, and is passionate about creativity. When she’s not writing (or talking about writing), she enjoys discovering new places, gaining new perspectives, and collecting souvenir pressed pennies. Follow her on Facebook, Instagram, and Medium @courtneylandi.


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