Don’t Get Trapped by the “Benevolent Dictatorship” of Tech Employers

Last week I spent time in the Bay Area visiting clients, listening to them talk about their jobs and careers, getting treated to free meals at their workplaces, and generally standing in awe of the wealth on display in their company headquarters.

While none of my clients dislike their jobs, there was a surprising amount of “meh” and ambivalence. These people are good at their jobs, they regularly learn new things, they enjoy succeeding and solving hard problems, the pay is good, the perks are great.

But some of them clearly aren’t fully satisfied by their current jobs. And what’s more, they don’t know what else they could or should do.

And I think the current role of tech employer as “benevolent dictator” is much to blame.

It’s Hard to Imagine a Different Life

These conversations reminded me of an exercise I do with clients when we begin working together. I ask them, if they had enough money to take care of their needs now and in the future, what would they change about their lives? What would they keep the same? (This is one of George Kinder’s famous-to-financial-planners three questions.)

More often than not, clients say they would like to do more of what they’re already doing. More travel. More video gaming. More time with kids. More volunteering. Rarely does someone suggest a radical change in their circumstances. The changes are quantitative, not qualitative.

Now, you can interpret this positively: “Wow! These people are already living their best lives and simply want more time for that same life.” And I gladly report that I think this is largely the case for many of my clients, who are pretty thoughtful folks.

There’s also a negative interpretation: that they simply can’t imagine a life other than the one they already have. I know I suffer from that lack of imagination.

So, here we have these people who aren’t unhappy necessarily, but yet they’re not particularly gratified in their careers in tech, and they don’t know how they should change it. Which, as you can imagine—or perhaps even identify with—can itself make you unhappy.

And Modern Tech Companies Make It Even Harder

I’m having these conversations, thinking these thoughts, while sitting in these gorgeous offices, eating free, delicious, freshly cooked, organic vegan meals, at one of several places in the office you can get food. Co-workers bring their dogs to the office. Some employers offer on-site childcare, free on-site massages and mani-pedis. And so on.

Hard to imagine feeling “meh” in the midst of all this, right?

Except, as I started to reflect, it makes Total Sense.

It is experience of and exposure to different ways of life, different ways of thinking, that enables us to imagine something different for ourselves.

A toddler has no clue what a fork is until they see their parent use it. Then the fork is no longer this foreign object; it’s something that can be a useful part of the toddler’s life.

Or, an example from my personal life: I had never camped a day in my life until my 20s. (I know, right?!) And I simply couldn’t wrap my head around how you camped, so I continued to not camp despite wanting to. Until I accompanied a girlfriend on a camping trip that she planned and executed. Once I saw and experienced it, I got it. I now started planning camping trips for myself, and it’s become a joyful part of my life. I just needed that up-front-and-personal exposure to cut through that mental paralysis.

How does this relate to working in tech,  you (rightly) ask?

As tech companies increasingly provide for your every need, you have less and less need to venture into the “outside world,” the world outside of your company/office/job. Either figuratively “outside” or, in the case of many offices in certain neighborhoods of San Francisco, very very literally.

Your entire life becomes increasingly integrated into your company/office/job. And, of course, living in some place like the Bay Area (or Seattle), even if you leave one company, you likely wouldn’t leave the tech industry in general because…well, what is there but the tech industry? Thar be dragons.

When you stop going outside, you stop spending time with people who have different careers in different industries, who have different hobbies, who spend way less or way more or way differently, who volunteer for different causes, who have different values. You stop seeing and experiencing different ways of living, working, and being.

The good pay and the awesome perks make it hard to leave a job in part because they’re “golden handcuffs,” to be sure. But I think these “all your lifestyle needs are belong to us” perks also create a more insidious hurdle to making a change.

When you no longer see and experience other ways of living, working, and being, you eventually stop being able to imagine other ways of living, working, and being. I think this increasingly all-consuming relationship you have with your employer might be crushing your imagination.

Many people in this world are stuck in a job or a life because they can’t change. They don’t have the money. Family considerations. What have you.

Most likely, you’ve got the financial resources necessary to change. You simply might just not have the imagination.

This benevolent dictatorship of tech companies is perhaps unavoidable if you do or want to work in tech. Certainly I cannot think of a major tech company that doesn’t provide many of these lifestyle perks. So, if we “have to” work in such an environment, how we can still maintain our ability to imagine an Other?

How can we still get exposure to other ways of living, working, and being? Exposure that might inspire us to make a change ourselves?

I don’t have an answer to that.

Travel is a classic answer to “how do I get exposure to other ways of life?” Except a lot of my clients travel, and it doesn’t seem to change the rest of their lives. And I don’t pretend to be anything more than an occasional armchair philosopher (is that redundant?), who is perhaps getting a bit intellectually self-indulgent with this post.

But I know that what I’m seeing in tech worries me for my clients because the abundance and wealth that seem so awesome have this dark side with the potential to leave us unfulfilled, and unable to find our way out of that morass.

You need two things to make significant change in your life, if you’re anything like me:

1. Financial resources
2. An idea of where you’re going

What are you doing to nourish both of those?

Do you want some help setting up your finances to give you more choice in your life? Please reach out to me at  or schedule a free consultation.

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