How to Handle the Inevitable Loneliness of Being an Entrepreneur

Like many entrepreneurs, I go to Starbucks a lot.

But not for the coffee.

Or the snacks. Or the ambiance. Or the cool music. Or the free wifi.

I go there because I’m lonely.
I go there because I crave human interaction.
I go there because I need to talk to real people every day.

That’s something they don’t teach you at Harvard Business School. Or at the Chamber of Commerce. Or in the pages of FastCompany magazine.

Being an entrepreneur is bloody lonely.

Don’t get me wrong. I wouldn’t trade my job for anything on the planet.

The fact that I get to make my own schedule, make my own decisions, make my own money and make a measurable difference in the world – all while doing what I love – is an honor and a privilege.

Oh, and the eight-second commute isn’t bad either.

But. When the (inevitable) loneliness starts to creep in like a toxic mist, you need to use every ounce of your creative capacity to stay connected, stay supported and stay afloat.

Otherwise the isolation will drive you insane, and will drive your business into the ground.

Here’s a collection of strategies to help you handle the loneliness of that comes with the entrepreneurial territory:

1. Detect the tremors. Like a seismograph that monitors tectonic activity, your goal is to identify the vibrations of approaching loneliness. Even if they’re just minor tremors. Think of them as an early warning system to take preemptive action against the onslaught of aloneness.

Ideally, the secret is to listen to your body. After all, it will never lie to you. It just depends on how you manifest anxiety physiologically. Do you sweat? Get headaches? Get heartaches? What happens to your body when you realize that you’ve been stranded at your desk for six hours without a single shred of human interaction?

For me, I experience a steady (but not overwhelming) flood of mental panic. It’s miserable but manageable. And most of the time, I can nip it in the bud before it morphs into a full-on freak out.

But it wasn’t always that way. When I first started my company in 2002, I didn’t quite have the mental, emotional and spiritual constitution to handle such anxiety. That was usually around the time I’d crawl into the fetal position and cry myself to sleep in the corner. Good thing I learned how to detect the tremors. How will you pinpoint impending loneliness?

2. Get the hell out of the house. If you work out of your home, physical displacement is a crucial component to success. Not only to prevent you from losing your mind and pulling each of your individual hairs out with a needle-nose pliers. But also for supporting, enriching, inspiring and informing your work.

What’s more, physical displacement alters your routines and patterns. Which stimulates creativity and feeds your social spirit. Even if it’s just for five minutes. What’s more, getting your self-employed ass out of the house actually makes more you a more relatable entrepreneur.

Like poet John Lecarre said, “A desk is a dangerous place to rule the world.” My suggestion is to build it into your schedule. Even if that means taking your laptop to Starbucks for one hour every afternoon. You’ll be glad you did.

Especially if that cute barista with the two-toned hair and the shoulder tattoos is working. How many hours straight (with no break) did you work yesterday?

3. Align with the like-hearted, not just the like-minded. If all you do is hang out with people who think the way same as you, you won’t learn, you won’t grow and you won’t be pushed. Switch it up. Find people who share a common constitution. A mutual why. A shared purpose.

I call these individuals “like-hearted,” and they’re essential to combating entrepreneurial loneliness. They will ignite your spirit faster and brighter than people whose brainstuff is nothing but a mirror of your own thinking. Ideally, for every like-minded person you spend time with; find three like-hearted people to balance the ratio out.

Still hang with (some) people who think like you. Just remember: When you surround yourself with those who get it – and, more importantly, those get YOU – winning is three times easier. Minimum. Do the five people you spend the most time with ask the same questions as you?

4. Make use of every medium. I’m tired of reading articles about how text messaging, instant messaging, Facebook, Twitter and other social media outlets are time-wasting distractions.

First of all, when you’ve been sitting at a desk in your basement for three days straight with nobody to talk to but your goldfish – who, by the way, has been really whiny lately – you will welcome whatever form of communication you can get your mitts on.

Secondly, for those of us who work remotely (or with clients that we never actually meet in person), electronic communication is all we have. Don’t let some conservative teabagger from FOX News convince you that Twitter isn’t worth your time.

Look: Do what you need to do to get your fix. Indulge in your humanity with whatever mediums work for you. Just don’t do it at the expense of executing what matters.

Otherwise you’ll get sucked into the seductive vortex of instant communication and wind up trading loneliness for out-of-business-ness. How do you stay connected during lonely days?

5. Invite people to virtual lunches. This strategy saved me. Seriously. If didn’t do regular virtual lunches with the same few people each month, I would snap like a Slim Jim. Not just from the loneliness, but from a lack of seeing the people I love. Especially the ones who live out of town that I only see five times a year.

If you find yourself in this situation, here’s how you do a virtual lunch. About a month ahead of time, decide on a call time that’s convenient for both parties. Remember to be cognizant of differing time zones. On the day of, cook, prepare, order – or, if you’re Ted Nugent, kill – your lunch for the appointment.

Then, at the agreed upon time, sign onto Skype. And the spend the next sixty minutes of your lunch break sharing, listening, eating and connecting with someone who’s important to you.

That’s it. It’s easy, free and fun. Plus you don’t have to get dressed. Which, depending on who you call, might be very awkward, or totally awesome. You may never hang up.

Actually, forget that last suggestion. Wear clothes.

Either way, doing regular virtual lunches – say, three a month – is the perfect way to spice up your weekly schedule. Sure beats sitting on your couch watching Tropic Thunder for the sixtieth time while eating a cold can of Schnuck’s Chili Beans and feeling sorry for yourself. Whom could you invite to a virtual lunch this week?

ULTIMATELY: Loneliness is an inevitable landmark of the entrepreneurial landscape.

Not that you would trade in your lifestyle.

But that’s the thing about a career.

A career won’t curl up with you on a cold night.
A career won’t listen to your problems without judgment.
A career won’t send you a text message that makes you laugh until you pee.
A career won’t call you on your lies and delightfully disturb you into becoming better.

You need people.
You need social interaction.
You need conversation with other human beings.

Otherwise you will go crazy.

Now if you’ll excuse me, I’ve been sitting here in my living room for the past six hours working in my pajamas, and it’s probably a good time to take a Starbucks break.

God I hate getting dressed before noon.

How do you handle the inevitable loneliness of entrepreneurship?

For the list called, “34 Questions to Keep Your Company Growth Minded,” send an email to me, and I’ll send you the list for free!

* * * *
Scott Ginsberg
That Guy with the Nametag
Author, Speaker, Entrepreneur, Mentor

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