To distill 2015 down into a single phrase for me, it’s “Self-development is tough, but life is good”. In some ways, I worry my development and improvements have plateaued a bit through 2015. That’s a tough acknowledgement but something I can work to improve.

My expectations of 2015 were ambitious. When reviewing 2014 and starting 2015, I was optimistic especially in regards to where I worked:

I'm ending 2014 in a good place. I'm gradually becoming more optimistic and I've found like-minded people who care deeply about people. The company itself is working on interesting problems all while striving towards the goal of the workplace being a platform for happiness and self-actualization. I'm pretty excited.

Probably the biggest change was how that idea didn’t work out. It soon became apparent that the balance of rewards over the risks, and belief in the capacity that my previous job was no longer a good fit for me. After much consideration, and some delightful conversations, I joined Stripe in August of 2015. It's been pretty great. I didn't expect that from January of 2015 to August this would happen, but that's the great thing about life. When we expect things we seldom get them; embracing the unexpected nature of life and preparing ourselves to be the best we can be we have great opportunities unfold in front of us. We can’t attach ourselves to any outcome, because we do not decide the outcome only how we handle ourselves. The best lesson I learned from this experience is that it’s important to witness how people respond in crisis before making decisions. I still have a lot to learn. A lot of self to develop, in fact.

And Self-Development is tough!

This is an area I’ve been focusing and studying on for 4 years and it isn’t getting much easier. Sometimes it feels it is getting harder. The changes within myself are more subtle, too. Whatever I’ve been reading or studying lately is more difficult to integrate and interpret. Essentially, I think I’ve read most of the books aimed at the layperson and moving into more abstract readings or research papers. This knowledge is powerful but it’s more difficult to integrate and interpret into my life. Reading takes more time but I have time. Every year, I get at least 365 days to use!

I’ve started reading (or re-reading) some of the earlier books on self-development which has had an interesting effect. Many of the previous books that had a powerful impact and were hugely inspirational are still great reads, but now they better help me articulate concepts and messages. The first read I was inspired, the second I started to understand. Maybe the third read I’ll be able to explain! I’m working on that in the form of blending ideas from, for example, 7 Habits of Highly Effective People, Flow, and The Four Agreements. With each read this becomes a lot easier and better articulated.

But the real reason for losing some of my edge with self-development is not keeping in close contact with people who push me along this line. I really want to get better about this. I usually wait until someone else reaches out ot me, and that isn’t fair. I need to get better at cultivating and maintaining positive relationships. Relationships are important, and they aren’t just about friendship. Last year I was asked, “Why do I coach?” and it was entirely about relationships. I started the year intending to begin to get certified as a professional coach, but the timing didn’t work out and with the job switch it likely would have been impossible to finish without great inconvenience. I did some coach training, and began actual coaching, but have a long way to go.

About coaching…

Reading Erich Fromm’s Art of Being made me realize the importance of coaching as a transitionary role, and to set expectations about that clearly. Interdependence, not codependence or independence, creates long-lasting growth spirals where people expand their influence and effectiveness. Relying on a coach to get started, with periodic check-ins, is the best way to do this but the coaching relationship must end at some point. That point is probably sooner than most people would like, but this is for their own benefit. Any time you have a coaching-style relationship, it’s too easy to fall into a codependent and paternalistic relationship.

I’m excited to do further coaching in 2016, but I have to cultivate an environment where that’s possible. I don’t think it’s feasible to get certified in 2016 which is disappointing but I can make it a priority for 2017.

And those annual focal points?

For the last few years, I’ve written out the primary areas of focus for that year. This is where I should invest 80% of my time. This idea was borrowed from Peter Bregman’s 18 Minutes, which is definitely worth the read if the idea of setting focal points for your year is intriguing.

  • More effective conversations

  • Travel while working
  • Expand my capacity for building products
  • More public contributions
  • Focused and specific writing

So how did I do? Oof! The final two items should have not even been there. I did absolutely nothing noteworthy regarding public contributions through the entire year. My writing fell off as I fell into a malaise and switched jobs. I wanted to write, but few things came out. Through the entire year I wrote 6 things. That’s awful. I had many drafts, but eventually I discarded the drafts and just gave up trying to post things. This really must change for 2016. Writing is such a great way solidify my understanding of what I’m reading and learning, and my daily notes on what I learn aren’t enough.

Building products has been great. Over the last year a friend and I built Done Did.

It's sort of like Twitter, for your software.

It's sort of like Twitter, for your software.

Done Did is a tool to manage software changes and publish those changes to users. This is a sorely missed part of relying on other people’s software, and as someone who builds software we don't give enough conscious follow-up to the work we do. I didn’t do a great job thinking about this as a product. We looked at what other people did but that wasn't very helpful to our end goal of creating a cycle of celebration of progress and more deliberate work.

I still improved through this. As we went through the product development process I thought of better ways to do things. Often I stopped and reflected on how I approached what we were going and practiced articulating ideas. Most importantly, I continuously asked myself what I would do differently the next time. This led me to a startling conclusion: I almost never actually ask myself, “What would I do differently the next time?” At least until the next time is here, and then I think how things went in the past, and try to desperately remember.

Fortunately this is software and the great thing about software is how easy it is to go back and change things. All those times I’ve proactively asked what I would do differently have gone into another project I work on. I’m also rewriting The Daily Practice. This means taking a much different approach to building it that I think will greatly improve the end result.

The effective conversations was probably my best area through the year but also highlighted some failures. I had many, many great conversations with such a large group of people. I feel extremely privileged to do this. It wasn’t perfect, I tend to take some people for granted and those are the ones I should communicate with the most. My kids are at an age where they have many ideas, thoughts, and struggles in daily life. Rather than give them advice I should stop, sit down and listen more. Being a parent is tough, because it feels as if the right answer is always advice. Advice isn’t effective when what is needed is acknowledgement.

I didn’t do great on maintaining and cultivating relationships I already have. I sit idle while other people reach out to me. This inevitably causes those relationships to wilt and it’s all on me. I’m going to work to improve on this.

Travels were pretty good even though I didn’t quite exceed my goals. I spent all of June in Japan, mostly working with a 16 hour time zone difference. The kids went to Japanese elementary school! I’m hoping to repeat this in 2016 because it was a great experience. My work environment there is cramped, but functional and has a nice view. It makes me appreciate my wonderful office at home a lot. The kids were great, and learned so much about the culture and language there in such a short time. We didn’t do a lot of working US-based trips, which is understandable because the kids require extra effort when we’re away from home.

So... much... whisky.

All ready for school, and excited to be there!

All ready for school, and excited to be there!