How to Be a Socially Anxious Entrepreneur

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Want to know how bad my social anxiety is?

I used to have a process for sending an IM to a friend. You read that right — I didn’t say a stranger. I needed a process to reach out to a friend.

  1. Triple-check the message for potential alternate meanings
  2. Worry about it constantly until I receive a reply. Check back several times an hour to see if I’d just missed the reply coming in.
  3. Don’t look at the reply immediately. That would make it real. I needed to take several minutes before I was ready for that.

That is no longer my process, but the underlying anxiety has not gone away.I struggle every day not to fall back into that trap.

Needless to say, I couldn’t become an entrepreneur like that. I dreaded every email, every call, and even every text. Entrepreneurs need to communicate regularly with strangers, acquaintances, and friends, and that amount of stress would have overwhelmed me.

I had experience with overcoming emotional and mental issues in the past. After my divorce, I went on what I now call “the year of 50 first dates”. The goal of that venture was to overcome my fear of dating again.

Going on that many dates forced me out of my comfort zone. I made rules for the process. For instance, I would ask a girl out after no more than a dozen messages (for dating apps) or two social events. Making these rules stopped me from using my favorite cop-out of “I’ll just do it next time”.

I needed similar rules for my entrepreneurial venture. These rules had to force me into the very type of social interactions that I wanted to avoid.

Here are the rules I used.


Rule #1: Answer Every Phone Call

My voicemail used to get a lot of use. I can’t say that I screened my calls because that implies that certain calls would get answered. I ignored everyone equally. I was as likely to pick up for a vacuum salesman as I was for my siblings.

That needed to change.

Customers would expect a human, not a machine. The rule was as obvious as it was daunting. I needed to answer every single phone call.

I didn’t even make exceptions for calls my phone labeled as “spam likely” or “unknown”. If you called, I answered.

The only exceptions I made were calls that came in while I was asleep or in situations where answering the call would be inappropriate or unhelpful. Dinner wouldn’t stop me, but a noisy street or the bathroom would. I don’t care how important you are, nobody should be answering phone calls while on the toilet.


Rule #2: Set a Deadline for Every Email

Emails were such an easy thing to delay. The excuse of “Oh, I guess I didn’t see it.” is a harder sell for texts and phone calls, but the email spam folder always provided a scapegoat.

In my new framework, if an email deserved an answer, then it required a deadline. I treated them like any other item on my to-do list.

The process was relatively simple. When an e-mail came in, I would go through the following steps.

  1. Determine whether it needed a reply.
  2. If it did, answer it immediately if possible.
  3. If I couldn’t answer it yet, determine a date when I believed I would have the ability to answer.
  4. If that date was more than a few days away, send an email letting them know that I needed some time before I could respond.
  5. When the deadline arrived, answer if possible. If not, then repeat steps 3–4.

The steps were more formal than they were complicated. And that was the point. By having a process, I knew whether I was abiding by the rule.


Rule #3: Give Each Task the Focus It Deserves and No More

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This one was about getting to the core of anxiety. I used to treat each email, each text message, and each phone call as the single most important interaction of my life.

On the one hand, each of your friends is important. And every customer deserves your best. On the other hand, this was tearing me apart.

Every rejection left me broken.

Every unanswered text message was a statement. And that statement read “Zak, I’ve had enough of you.”

I felt like I was leaving a piece of me with each of those interactions. And I only had so many pieces left to lose.

Needless to say, this framing had to go. I knew that I had dealt with rejection in the past. I was at one point a 5’5″, nerdy, twig of a teenage boy in the dating world, which is a true crash course in rejection. More recently, I had experienced a significant amount of rejection when I switched careers from chemistry to data science.

I began to evaluate what tactics had worked well or poorly for coping with those rejections. After eliminating tactics that were too situationally dependent, I ended up with the following rule.

My focus can narrow to a single person or a single message, but I need to always be ready to shift my focus.

What does that mean?

It means that the message I’m writing right now can still get my full attention because my reader, my customer, or my friend is worth that. But I need to have other tasks waiting in my queue.

As soon as I hit the send button, my focus switches to those other items. The sent message doesn’t fall away from my mind, but it is no longer my top priority.

With this focus shift, I give that one message the focus and respect it deserves without letting it consume me. I don’t have to fear the send button because — instead of starting a cycle of worry — it triggers a focus shift. That energy that was spent worrying about the message that was already sent can instead be devoted to items that I still have some control over.

And that is the key reason for rule #3. The worst part of my anxiety is triggered when I focus on what I can’t control. I’m sure many of you have heard of the serenity prayer (or at least one variant of it).

God grant me the serenity to accept the things I cannot change, Courage to change the things I can, and wisdom to know the difference.

I know that the sent message is out of my control. Rule #3 is a constant reminder to simply accept that and replace it with the next things on my to-do list.

What happens if my to-do list becomes empty?

If you’ve ever been an entrepreneur, you know the answer to that question. Your to-do list is never empty. But I do verify what the next items are before I hit the send button, allowing the shift to occur immediately. It’s a hassle at times, but if the side effect is that I’m a bit too organized, that’s a price I’m willing to pay.


Final Thoughts

These three rules have become crucial parts of my entrepreneurial and general life experience. I hope that they provide as much value to you as they have to me. I also look forward to hearing what methods you use to manage your social anxiety.

This is not the story of a miraculous recovery. I still suffer from social anxiety, and I always will.

I’m not going to tell you that being an entrepreneur with social anxiety is easy. It would have been far easier to stay in the corporate world. But entrepreneurship isn’t about taking the easy road.

Entrepreneurship is not for those who are tough. It’s for those that make mistakes and learn from them. It’s for those that exhibit strength through vulnerability.

Entrepreneurship is for people like you and me.

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