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The Typewriter and the Outliers


I was in downtown San Francisco at a coffee shop with a longtime friend and coworker. We were spending the day reconnecting and working on our respective projects. Laptops were open throughout. As we talked and worked, an older man sat down at our communal table next to my friend. After setting down his drink, he opened his backpack and brought out…a typewriter. I was surprised and more than a little amused. This seemed so odd and out of place; the man and his tech didn’t fit in.

I made a polite comment to him, telling him I hadn't seen a typewriter in years. He was gracious, and we shared a quick laugh. But I still was amused and even took a quick anonymous phone picture. Even after I left and went to a late afternoon coaching session, the image stayed with me. I planned to post the picture and story on my social media accounts over the weekend. No slam on the man, just a quirky San Francisco moment. But I had a change of heart.

I remembered the man’s polite demeanor and the quiet way he went about his writing. He took obvious pride in his work; this was his craft. This man reminded me of another client, who I really value working with. She’s a gifted technologist who can go deep in a wide range of technical spaces. My client has a huge range of interests and is an accomplished artist who’s performed in multiple venues. She takes great pride and can be obsessive in building her knowledge and contribution. Her craft: pulling together technology teams to build challenging products and services. But she faces a challenge because she sees the world differently. Like the man with the typewriter, my client is an outlier.

The path she’s created is tough and her methods are unique. She’s growing into a strong team member and leader with an insatiable curiosity. Her work ethic is off the charts and applies to both her career and personal passions. She’s far from the profile of a typical millennial.

But she faces the challenge of being an original and not fitting “the model” we create. Graduating from a top school, a first job at an iconic company, expectations dictate she continues along this path professionally and personally. But that path and those interests aren’t a part of her. She’s deeper, more curious and wants to be a passionate expert in her career and personal life pursuits. She’s an outlier.

There’s pain being different and outside of the career path bell curve. She’s felt that pain often accompanied by doubt and loneliness. She’s preserved and has grown significantly both professionally and personally.

Like the man with the typewriter my client is a craftsperson using her unique skills and tools to produce consistent high-quality results. I’d argue my client and the man with the typewriter think and do things differently, but usually produce better results.

There’re two core questions:

• If someone can provide strong solutions to their organization, and be a good team member, should we care if they have different methods, tools and path? I hope we don’t.

• If your skills and crafts are unique, you’re a great team member and consistently produce solid results, how much do you want to adapt? I hope the pressure to “conform” diminishes as an outlier gains personal strength and satisfaction.

I’ve love the unique people in my life and value what they share with me, both personally and professionally. They’ve made me a better leader, coach and person. I'll always welcome outliers into my life and work.

A footnote: I never wrote the Social Media post and deleted the picture. I talked to my client the same evening. That was the better path.

I'm a certified Career Coach, long time Silicon Valley Recruiting Leader and lead Job Search, Career Development and Career Success at the Wharton Executive MBA Program in San Francisco. I also coach through HireClub.

If you’d like to discuss the ideas in this post or other areas where Coaching might help - I’d love to share. All initial sessions are free and we dive right in. There is never any pressure or push.

My email is

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