Keeping in Touch

I’ve been talking with a few people about the concept of keeping in touch. Like most things, it gets more interesting the more you look at it.

Keeping in Touch means meeting over video, phone, or in person at least once per year.

Glen’s arbitrary definition

There are multiple categories, I think. Personal, Professional, and Sales contacts. I don’t think they are identical.

Personal Contacts

These are people like high school or college friends or even family members. I try to keep in touch with my sister Abigail at least once a month. These are people you have been close to, but maybe they moved away or got married. This is a big reason people drift apart.

Professional Contacts

These are co-workers, or colleagues you know from a professional setting like work, meetups, or conferences. This may include mentors or even mentees. There are several people from my past that I try to stay in touch with. People who you sit next to for years somehow become difficult to stay in touch once you move to a different company.

Sales Opportunities

This is a specialized category, but basically this is maintaining contact with a prospect to keep the relationship warm until an opportunity to sell presents itself. Good sales people know exactly the right way to stay in touch. Many marketing techniques like drip-nurturing are trying to automate this process.

The Tricky Part

Imagine this chart and enter in your own numbers.

People I want to keep in touch withPeople I actually keep in touch with
Want vs Actual Keep in Touch

Almost everyone I talk to says the same thing. The reality is that our list of people we should keep in touch with is much higher than the list of people we actually do keep in touch with. One person pegged it at 10-1 for personal and 20-1 for professional. Why is this?

Keep in Touch Anxiety

It’s actually quite difficult to keep in touch with people, especially if you are even mildly introverted. There are many steps that can lead to failure and potentially embarrassment. Here are some:

  1. Excuse to connect. People need a reason to be reaching out. It’s hard to say “Just to stay in touch”. Rather a specific reason feels more comfortable. Example: Congratulations on your new job! We should get lunch!
  2. Scheduling time with another person is a hassle. It’s several emails going back and forth with frequent cancellations. Maybe calendly helps, but usually it’s just hard.
  3. Location sometimes gets in the way especially when people move and it’s not easy to meet for lunch. When you travel to a city, you should probably meet people while you are there, but we either forget or feel weird about doing that.
  4. Topics: what do you talk about? Many people will not even reach out because they don’t know what they would talk about. It’s pretty awkward if two people meet in silence.
  5. Life changes often are connected to this. When one person gets married or has kids it often leads to a slow decline of connection. This may also lead to resentment between people who loved their connection and now have feelings of loss/grief.
  6. Channel of communication is often a mismatch. One friend uses Instagram for this. Another uses texting. Email feels like a professional vehicle. It’s hard to know the right way to contact someone.
  7. Authenticity vs Transactional. Sometimes people feel that keeping in touch is “sales-y” and transactional. is your relationship secure enough to feel authentic? Not always.
  8. Pandemics present a new problem where people meet via zoom. Lunches are much more relaxed compared to a 30 min zoom meeting.

All of these reasons add up to a bunch of anxiety associated with keeping in touch with people. This is especially true for introverts, but even my son (high extravert) struggles with knowing the right way to do this.


The more I talk to people, the more I can see that networking has become complicated and even negatively tarnished. It is an important part of capitalism and human connection, but technology has made it problematic to say the least.

We collectively do not know how to approach it. We aren’t taught how in school. We aren’t trained at work. We are all left to our own devices and the lucky ones benefit from doing it right.

I’ve tried to tool Lunchclub, but it feels wrong. First of all, you can’t actually book time at lunch. Secondly, it gives me no options of whom to meet. I don’t know, it just feels wrong to me.

Wrap it up

Well, that’s what I’ve got so far. If you would like to meet with me, I have a new meet page. I purchased TinyCal for the booking. It is a $20 one time fee for a lifetime subscription. Basically, it is a Calendly clone. When was the last time there was a one time for lifetime license? Nice. So far, it works well.

If you have thoughts, please comment below. My comments are still a bit broken until Jetpack fixes their system.

Whatya think?