3 posts

You can get into a rut while building your dream company.

For all of August and all of September I’ve been a coding machine. On average I’ve spent about 12 hours a day working on our software platform. I’ve cranked out over 12,000 lines of code across 300 files. To be creating again feels absolutely incredible! Ending each day having produced something material and useful is a real joy, and one I’ve sorely missed.

My personality tends to be an all or nothing personality. Go epic or go home! There is no room for average. When deciding what projects to do for Hack Day at my old job it had to be an ‘A’ idea or it wasn’t worth doing. Be brilliant or nothing at all! (As an aside, this is probably why I am obsessed with finding “the middle path” and talk about it so much. But that’s for a later post.)

My personality also tends to be a perfectionist personality. It’s either perfect, or it’s wrong. I loved playing baseball when I was a kid. Our team could win, and I’d have gone 3-for-4 at the plate having driven in the winning run and I would obsesses over the one at bat I didn’t get a hit. In more recent years my team would put out an amazing release with new features, ahead of schedule, and I would obsess over the one small presentation bug we didn’t catch in testing.

Both of these personality traits offer advantages and disadvantages. Like Voltron, these traits become something more powerful when combined, multiplying the advantages and disadvantages. Last week the disadvantages got multiplied and brought the coding machine that was me to a complete halt.

It happened when the integration with another software platform I was working on didn’t work the way I thought it should. They key words here being “the way I thought it should.” The integration with this platform is simple and worked just fine. Their Python library made everything easy. My code works. But it doesn’t work the way I want it to. It isn’t elegant. It isn’t perfect. And because it isn’t perfect my brain and ego rejected it.

I then became singularly focused on finding perfection. I became angry with the software platform I was integrating with, and I became angry with my own design and code. I hate inelegant solutions – they make me feel like I’ve missed something simple and obvious. I became stuck and couldn’t code anymore. I shut down.

For the first time I didn’t want to work on building our company. This lack of activity lead me to feeling very badly about myself, which only compounded my “stuckness.” How can you get into a rut while building your dream company? How selfish! How ridiculous! It should be impossible!

But it is not impossible because we are human. We are not robots. We have emotions. No matter how introspective and self aware we think we are these emotions tend to always get the upper hand when it suits them. And when this happens we have to have to take a step back and have compassion for ourselves. We have to forgive ourselves, laugh at ourselves, and move on.

So after struggling for a few days of uselessly refactoring code, and writing and deleting code, I did just that. I put the laptop away, went to a bar to watch the Indians game (I gave up TV to help trim my living expenses), and gave myself the next day off. No hustle shaming please!

And you know what? It worked! The day after I had a delightful and productive company meeting (which I will talk more about soon) and started coding the next item on our roadmap. Since then I am back on track and am feeling productive and good again.

When trying to be compassionate and kind human beings it is most natural for us to focus on how our words and actions affect other living beings. We strive to be selfless. We think about how we can reduce suffering in other beings. This is very noble. However, in doing so we forget to think about ourselves and our suffering. We forget to care for ourselves.

This is a concept my team members and I talk about often. We talk about how as a team leader you cannot effectively take care of other people if you do not take care of yourself. We need to remember to include ourselves in the group of people we are taking care of.

The airline industry knows this as well. They tell us that in the event of a loss in cabin pressure we are to put our masks on first before helping other passengers. Be kind to yourself. Have compassion for yourself. Put your mask on first.

Being supportive is a superpower.

It turns out my friends and family are pretty amazing people.

When we decided to start Shepyrd everything felt right. I wasn’t scared about starting a company. I wasn’t scared about the financial risk. I wasn’t scared about our future success. I was scared about telling my friends and family.

Throughout my life I’ve sort of gone with the flow, surfed the waves where they took me, and done what was expected of me. In video game parlance my life was a game “on rails” — the experience I was having was amazing at times, but the trade off was that I wasn’t exercising any real freedom of choice. I was happy to go where I was expected to go and have the experiences expected of me.

For a long time living my life this way worked out pretty well. I’ve been professionally successful, met wonderful people, had ridiculous fun, been exotic places, eaten gourmet food, driven fast cars — the works! I cannot lie, it’s been a pretty great roller coaster ride.

But a roller coaster is the same as a video game on-rails. It’s an experience somebody else dreamed up to be appealing to the masses. Eventually it’s time to get off of the ride and start making a ride that is appealing to YOU, to start making the experiences you dream up. I am fairly certain this is a universal truth of life. Life is what WE make of it, why leave it up to somebody else?

So here I was getting off the roller coaster, and I wasn’t scared. Trading in the safety and security of a pretty good ride for the chance at something truly spectacular. The only thing that scared me was telling my friends and family.

And I was scared to tell them because I was scared I lacked belief in myself. Scared that as soon as I heard the words come out of my mouth I’d discover myself to be a fraud. Scared that their imagined lack of support echoed my own self doubt. Scared I would slink back to the safety and security of the roller coaster.

But guess what? None of those things happened when I told them.

It turns out my friends and family are pretty amazing people! Since we told everyone about Shepyrd, and I’ve announced my intentions to do this full-time, I’ve been met with nothing but positive support from everybody around me!

This is an unbelievably great feeling, thank you. Your support gives me the courage needed to tackle the difficulties that inevitably lie ahead. To know that you are all with me as I take on this venture feels truly remarkable. Your support makes me feel like I can build my own roller coaster and have the ride of my dreams.

Being supportive is a superpower. Use if freely, use it often. Teach others to do the same.

A beginning is a very delicate time.

On August 1st Julie and I created a technology startup company.

Up until this exact moment things had been pretty dire. I had no idea what to do with myself, or what my purpose in life might be. Truth be told, I thought I was done with technology, and the choices I was debating reflected that. Maybe I’d become a chef. Maybe I’d open up a bar. Maybe I’d solve crimes as a private detective. Maybe I’d finally become a Buddhist monk.

But then I decided to go down to Columbus, OH to the PyOhio conference. I desperately needed to get out of the house, and several of my friends and ex-colleagues were speaking and helping out with the event. It would be good to re-connect with all of them and shake up my routine.

That weekend proved to be a turning point for me.

Listening to all of these wonderful and positive people tell their stories reminded me that technology, when used correctly, can be a transformative force for good. It reminded me of my personal mission: to build technology that makes the world a better place.

Speaking with one of the managers I used to coach, who is now also a friend, I was reminded how passionate I am about taking care of people, helping them grow and be successful, and coaching other people to do the same.

I didn’t know it that weekend, but something started to change inside of me. Frost began to melt. Depression turned to hope. A way forward began to crystalize. A new beginning started to take shape…

Four days later, on August 1st Julie and I created Shepyrd, a technology startup company dedicated to helping you manage your team more thoughtfully and effectively. We’re going to take all of our experience and expertise and share it with everyone through simple and useful tools, resources and education, consulting, and a thriving community passionate about our mission as well.

I’ll start talking more in-depth about exactly what this all means in the weeks and months to come. I hope you’ll join us on our journey!