STARTUP

How to Answer Your Family’s Questions About Your Startup This Holiday Season

The holidays can be tricky enough without your family’s skepticism about your startup. Here are 10 tips to be ready.

Share on
BY Eddie Yoon - 20 Nov 2017

How to Answer Your Family's Questions About Your Startup This Holiday Season

PHOTO CREDIT: Getty Images

It has been nearly half a year since I left my job as a senior partner at a consulting firm to create my own startup, a think tank and advisory firm on growth strategy.

I've had a blast writing about 20-year trends like how cooking will become the new sewing. I've traveled the world to speak at conferences and continue to learn from startups and high-growth companies. I've been blessed with cost-effective and high-impact ways to market my new venture--my book was just named the top marketing book of the year by Strategy and Business, and I got a chance to talk about it on MSNBC.

Yet despite this momentum, I'm only cautiously optimistic. Who knows if it will last? When adversity comes--and it's a question of when, not if--will I handle adversity well? Will I need to go crawling back, hat in hand, to find a 'regular job'?

These questions always linger in the background, but often rise to the forefront during the holidays, Soon many of us will trek a long physical and possibly emotional distance to see family and friends, most of whom mean well but some of whom can be just mean at times.

Family members can inundate us with questions. Some are benign, but others have a bit more bite, like, "Aren't you worried about the risk?" or "Isn't it about time you give up and get a real job?"

In general, these questions come from a place of love and concern--as well as deeply held dreams for the future. As a child of immigrants, it was my parents's dream for me and my brother to get a good education and a job with a broadly recognized company, steady salary, and good title. Many immigrant parents took big risks as entrepreneurs so that their children could be professionals without that risk.

That said, with just a little bit of preparation, there's no reason this season can't still be the most wonderful time of the year. Here are ten tips to help you navigate the questions from your family during the holidays:

1. Ask good questions.

The best way to counter nosy interest in your startup is to be nosy yourself. Be ready with great, interesting questions for your family.

Look for ways to segue from your startup to the other person's work or interests. Remember, people like to talk about themselves.

2. Pick a few good stories to share.

Winnow your startup war stories to a few really good ones. If you're really concerned, practice by recording yourself on your smart phone. It can help you tell a great story, satisfy the crowd and move on.

3. Preemptively share a few insightful articles and ideas.

Share articles about your industry or a similar startup ahead of time. Refer to the articles when the conversation comes to your startup. This lets you talk about startups or industries in general, not just your own startup.

4. Focus on your favorites.

Pick your favorite family member or friend and get your startup conversation out of the way on friendly turf. That way, you can honestly respond later, "Oh, we already talked about that. You can ask them."

5. Enlist allies.

You can also enlist your favorites as allies. Confide in them and tell them your concerns. Ask them to help out as your wingman so that they can help you manage the conversation and family members.

6. Indulge and recharge.

Find something you really enjoy and indulge preemptively. Eat your favorite foods, exercise, or go to the movies. A busier schedule can cut short unwanted conversation or give you something to look forward to post conversation.

7. Hide by helping out.

There's a lot of cooking and cleaning that goes on during the holidays. Roll up your sleeves and help out. You can be a help while you hide in the background from unwanted discussions.

8. Set boundaries.

Think ahead of time what you are okay or not okay talking about. And be firm with a smile when it comes up and say you'd rather not talk about it. It's better to be firm upfront than frustrated later.

9. Work on specific relationship goals.

We all have someone in our family with whom we wish our relationship was a little better. This can serve as an important excuse to re-direct the conversation from your startup--you can honestly say you have a more important topic to discuss.

10. Sleep in.

Catching up on sleep can be a huge benefit, in general--it'll make you healthier once you return to the office. And it can show your family how hard you've been working.

Go to bed early if the conversation turns unpleasant. Or take strategic naps.

Good luck and feel free to share your best tips on this with me.