The Great Unknown

This is my attempt at a founders story. Why I left an awesome job with an amazing team to venture into The Great Unknown of entrepreneurialism. The Why, in other words, I started Sendline.

Last fall, we sold our house in Tacoma, packed up everything we owned, and relocated to Wenatchee, on the eastern fringe of the Cascade mountains. Warmer, dryer, twenty-six minutes door-to-chairlift from the local ski hill. As we settled into our new house, unpacked, I discovered a box of folders that needed to be filed. One of them was labeled, simply, ‘Development.’ In it, I had kept random things from throughout my career. An old career plan from REI where I had written ‘Leadership and communication (verbal)’ to the question ‘What knowledge, skill, or ability are you developing through this plan?’ Handouts from past leadership classes I had participated. Notes from my meetings with mentors.

A printed copy of an email from a boss of mine, Mike.

It was dated December 14, 2006. There was a deep crease through the middle. I guess at some point long ago I had folded it. An arrow I drew to the bottom of the page led to the notes I had scribbled from our meeting. ‘Need to work on leadership skills, how to present ideas, get concerns right out in the open to build relationships,’ and such. The email was titled, ‘TS Update.’ Mike had wanted to chat with me about some stuff.

Tom (this was before I added back the ‘h’),

I’ll be at HQ next Tuesday for a meeting. I’d like to review what we have for projects (yes, that’s still my responsibility).

That was Mike being the boss, as he needed to be. Then, below that necessary business, he continued:

Other topics I’d like to discuss:

  • Your future (where you want to be in the mix @ REI)
  • Some advice from me on what you should be doing to position yourself to get what you want
  • Adopting a mentor – probably someone @ HQ that you can use as a coach, teacher, confidant – someone respected by their peers, management, and direct reports – you know, kinda the direct opposite of me!

So some food for thought – mull it over – the times will be a changing and I want to make sure you’re able to get what you want!

That was Mike being more than my boss. That was him being my mentor and advocate, my champion. It’s not a coincidence I accomplished more with Mike than at any other time in my career.

Over a decade now has passed since he sent that to me, since we sat down in the café and talked about my future, his future. More accurately, twelve years, five months, and twenty-one days. Twelve years… In that time, I’ve held many different positions, moved desks from one end of campus to the other, and yes, last fall, packed up everything we owned to move our family across the mountains. Yet still, after all those years and all those moves, all the changes life has brought us, I held on to that old, folded copy of Mike’s email.

That’s why I’m here. That’s why I left to do something I’ve never done before. That’s why I started Sendline.

The world needs more Mikes. More bosses from whom, many years and however many moves later, we’ve saved their notes, wrinkled and worn, because those notes remind us how much they cared. I started Sendline because I want to share my story with other managers, as many as will listen and open themselves up to the possibility of what it looks like and how they can leave that kind of impression on those who call them their boss. 

Mike regrettably passed away a few years later, not suddenly, but way too soon. I still remember an afternoon, late, him coming into the shop asking me, ‘Hey bud, what’s on your mind?’ I can hear the tone of his voice, inquisitive, genuine, with an edge of anticipation for my answer. Wrapped up in my memory of Mike, I envision a world where all managers resemble him. Where they, as I once read, believe in their people, are humble, and care about them so they can be demanding, compassionate, disciplinary, praising and, maybe most difficult of all, risk not being liked.