A Founder’s Guide to Surviving Family Holiday Parties

The holidays are coming, and along with that will come many questions from well-meaning relatives about the “project” you’ve been working on… also known as: the startup you’ve been working night and day to get off the ground.

Navigating these conversations can be tricky, especially if you’ve had a rough few months (and let’s face it: what founder isn’t always having a rough few months?). Either you’re stuck explaining your idea to a bunch of people who are struggling to understand it, or you’re getting asked why you’re not making more progress. You might even get compared to other family members who are checking all of the “traditional” boxes when it comes to success. And if you’re especially unlucky, you’ll have to deal with some kind of emergency issue and deal with a bunch of judgmental comments about prioritizing work over family.

First: know that you’re not alone. Thousands of other founders are going through the same thing you are, at the exact same time, and they’re having just as rough a go of it as you are. Yes, even the founders who you think are way more successful than you. I promise: most of them have at least one family member advising them to quit now and get a nice, stable job. It’s just how the world works.

Next: prepare. Here are a few things you can do to make these parties as stress-free as possible:

Craft your family elevator pitch

If you’ve been a founder for a little while, you probably have a few elevator pitches up your sleeve already: one for customers, one for investors, one for other founders. Now, it’s time to create one for your family. For family pitches, it’s often best to keep things as short and sweet as possible, and make references to products that they’re familiar with. “Uber for X” is totally fine here, even if it’s not 100% accurate. The idea is to get them to understand well enough without grilling you with a bunch of frustrating questions.

Try not to be on call… or try to be very on call

If you have the kind of family that will be offended if you have to take a work call, do your best to get someone else to take over for the amount of time you’ll be at the event. If you have the kind of family who thinks leaving a party partway through is a sign of a strong work ethic and will get them to take you seriously… then definitely volunteer to be on call.

Get good at asking questions first

No one can grill you about your startup if they’re too busy bragging about the promotion they just got at work or telling you about the new puppy they’re training. If you control the conversation, you can easily avoid topics that you don’t feel like talking about.

Prepare to deflect

In the event that you get asked a question that hits a sore spot (”Weren’t you making more money at your last job?” “Would anyone even use that?” “Is this why I don’t have grandchildren yet?”), you’ll want to deflect gracefully instead of getting pulled into an argument or a conversation that’ll put you in a bad mood.

You likely know best what will work for your family, but sometimes cheerful agreement is the way to go. For example “Weren’t you making more money at your last job?” “Yep, but I’m way happier now!” or “Would anyone even use that?” “I’m not sure yet, that’s why I’m trying!”

Take care of yourself afterwards

Like I mentioned above: this experience is pretty universal. However, that doesn’t make it any less difficult. You still may leave the event feeling discouraged or full of doubt, thinking that maybe you would be happier if you found a nice girl or boy and settled down at a stable job.

That’s perfectly natural, but the key is to get yourself out of that slump as quickly as possible. Try to set aside a little time after or the next day to get yourself back on track. Maybe it’s just doing some stress relieving self-care, maybe it’s venting to a friend who understands. Either way, your goal is to get out of that mindset as fast as possible so you can go back to working on the startup you love.

Conclusion

The holidays can be difficult for everyone, and it’s no exception for founders. While family members can be well-meaning, they can also accidentally strike a nerve or two when trying to make small talk. With a little preparation and the right mindset, you can get through any event.

Postscript

If you’re one of the lucky founders whose family just gets it, congratulations! You’re very lucky to have that kind of support system. Try to be there for your founder friends this holiday season who aren’t quite as lucky.