An Unconventional Guide to a Meaningful Work Experience

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Is it possible to accomplish work without humans?

Even artificial intelligence requires the hands of a human to make work happen. Keep work human is an awkward thing to say if you think too hard about it.

It begs the questions:

  • What about work is not human?
  • When did work start becoming inhuman? Why?
  • What does it mean to have a human work experience?
  • How does an inhuman work experience change our relationship to work?

All great questions that I am seeking to shed some light on from my own experience as a 10-year veteran…

Help your users get what they want, not what you want

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I first read the book “Badass Making Users Awesome” by Kathy Sierra in 2018. Considerably late to the game given the book was released in 2015, but it’s still a book I return to every so often as a reminder of a core principle in product development.

Bestsellers are driven by word of mouth

The author suggests that word of mouth translates to an honest, non-incentivized recommendation about a product and the results that it derives. When a user gets a result they don’t just feel awesome, they are awesome.

All that matters after a user experiences your product is:

A love hate relationship with selling your stuff

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It’s a garage sale day and I hate it.

My spouse loves it.

It’s a day that brings childlike excitement to her eyes.

The date was set a week in advance and the preparation has been fast and furious. Full closet sweeps and diligent preparation. That’s the name of the game.

Every evening as I return from work, I am met with the full force of preparations. I pull my car into the garage. I can’t open the car door. Volumes of treasure are unearthed, relocated, and piled into the parking space next to mine. …

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I found myself in a peculiar situation as a leader.

I wanted to promote a direct report. My management disagreed.

My report had a great attitude, they were resilient in the face of change, they were skilled in their role, they were influential, and the work they brought to the table was making a measurable difference.

My management didn’t see what I could see. From their vantage point, my direct report needed to add additional experience feathers in their cap to prove their worthiness of taking the next step.

I made two key mistakes.

Mistake #1

I chose to take the side of my leadership instead of for my report.

I made a big assumption. I…

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I’ve been a “watch-ya-preneur”.

In early 2000, a neighbor shared the book Rich Dad Poor Dad with me. He was an entrepreneur building his first business.

We had talked about start-ups and he knew my frustration with my full-time job at the time.

I read the book in one sitting on a rainy spring day. I’d like to say that the book catapulted me into entrepreneurship, but it didn’t.

I spent my spare time reading about business, how to come up with ideas, design thinking, audience building, customer problem fit and lean startup. Pick your favorite start-up buzzword and process…

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Startups are not just for young people.

I recently interviewed for a role with a startup. The company reached out to me to inquire about my interest. I was flattered by the invitation but left the call flattened.

I’m in my mid-40’s. Apparently, old for today’s startup culture. I’m not trying to hide my age, but I got the sense that the recruiter discovered my age mid-interview.

We had a nice conversation, but at the end of the call, she added some filtering questions that left me feeling the very real effects of ageism.

Here is what she asked:

Are you comfortable working with young people?


Make things engaging and let the people closest to the work drive it

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When I was at Mailchimp, I started a bi-monthly cross-functional all-hands event. I was a co-producer of the event along with our Sr. Director of Engineering.

It sounds like just a meeting. It wasn’t. It was a production AND a program to generate cross-functional empathy for our customers and our teams.

The beginning

We started with four observations after listening to our product teams:

  • They were not clear on what was important to leaders
  • They rarely heard about customer impact after they shipped
  • They were no aware of all the projects that were happening

Keep your customer’s need front and center or let it go

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My friend lost his dog unexpectedly a week ago.

Losing a pet is like losing a family member. It’s painful.

I asked him what happened. Swallowing hard, he recounted the weeks leading up to her death. She had stopped eating and could only muster slight glances up from her bed despite calls to engage in play.

We chose to put her down, he said. It wasn’t easy, but when we realized that saving her life was more about us than it was about the dog’s well-being, we knew we were making the right choice.

It was a sad story, but…

3 steps to follow to avoid hurting others with your healing

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Truth begets trust in relationships.

Your willingness to be open and share allows people to see you for who you are. It fosters connection because people connect to the humanity of your story. Your story helps them understand themselves and their part in life in new and different ways.

But, there is a dark side.

Because we connect through other people’s stories we may see things in ourselves that we are embarrassed by, fear, or loathe. By sharing your truth, you unearth the truth in others that they may not be prepared to deal with. …

What pace are you setting for your team?

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If a man does not keep pace with his companions, perhaps it is because he hears a different drummer. Let him step to the music which he hears, however measured or far away. — Henry David Thoreau

What pace are you setting for your team? Is your team following or are they walking to the beat of a different drummer?

Here is what I know, all organizations have a rhythm. Your team will follow it to the extent that they know it and agree with it. If the rhythm is unknown then they will look elsewhere and find a rhythm.

Justin Zack

Project leader. Product thinker. Write about human things. Find me at

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