Category Archives: future

Listening to the clues about what’s working well: writing

I write down things I’m puzzling out, and I write down hints of things I might be good at. It’s useful to do both. Writing about my challenges helps me understand them better, and I often hear from people who identify with me, learn from me, and even share their own tips. Writing about my little successes seems a little more self-serving and egotistic, but it helps me pay attention to clues life gives me, celebrate the small stuff, and remember the good things. I’m looking for ways to make the most of this five-year experiment, so I’m on the lookout for strengths that I can build on.

At the last Visual Thinkers Toronto meetup, someone told me that how I share on my blog is working. People in the Emacs IRC channel tell me that they enjoy reading my posts. I often find myself sending people links to posts, sometimes posts that are years old.

So this writing thing… Hmm. Might be something there. What are some of the things I do in a way that might be different from others? If I can name those characteristics, I can then improve or at least retain them. =)

  • I write a lot. People boggle at this because they struggle to write once a week or even once a month. I write a lot because it’s my default way of thinking. There are a few things I think about privately, in sketchbooks and in text files on my computer. I share as much as I can on the Internet, though. It makes sense to do so – I can help other people along the way, and it’s easier for me to remember something if I can either Google it or ask someone to help me remember what I called it.
  • I write with happiness and enthusiasm. I’m naturally happy, I guess (happiness set point and all), and I consciously develop my ability to be happy. Not necessarily bouncing-up-and-down happy, more like… at peace with life. Besides, I have a pretty awesome life, so it’s easy to be happy about it. =)
  • I follow my curiosity. Can Emacs do …? How do I …? There’s no end to the questions I can ask, and therefore no end to the things I can learn and write about. It’s a privilege to have the space to be curious about things, so I try to justify that privilege by sharing as much as I can.
  • I’m good at analysis. I enjoy picking my thoughts and feelings apart in order to explain them. I like reading and I’m growing to enjoy listening to people, and that’s how I learn to recognize patterns and name them. I’m not super-awesome at it – lots of cognitive biases to work around! – but there’s hope for me yet. =)
  • What if I could get even better at this? What would better look like, if I built this up over decades?

Imagining the future:

Writing gives me an excuse to be curious. I write about useful and interesting topics in a positive, straightforward, well-reasoned, and creative way.

On occasion, I sit down and develop a topic much further, taking a comprehensive look at something instead of the scattershot approach of spur-of-the-moment blog posts. I review and summarize things I write about a lot, compiling them into blog posts and books.

Lots of conversations grow out of my writing, and my writing grows out of conversations. It’s an excellent way to hack around introversion, because people talk to me.

Even tough situations in life – deaths and other inevitable losses – become fodder for writing, as I try to understand and grow.

Because I write a lot, people can filter the topics to focus on what they’re most interested in, but still stumble across my other interests from time to time. I remember how to find things and can send people links quickly. I maintain an index to help people find things again, and I periodically browse random posts to jog my memory.

I keep my life simple so that I have the freedom to write about what interests me (no corporate shush policy) and to spend time pursuing what makes me curious. It might not be a glamorous life, but it’s a fun one. I save people time and open up new possibilities. I constrain my lifestyle to my budget, so people’s purchases or donations are icing on the cake – money that I use to learn even more, to connect with more people, to experiment with other ideas and tools, and to make strategic differences in other people’s lives. That way, I can always be surprised and happy when people give me some of their time (both in terms of attention and in terms of money, because money is time after all).

I manage to escape the nastiness that the Internet can sometimes have, or I survive it.

I live an awesome and well-documented life, and I make it easier for thousands of people to build on what I’m learning.

People want to avoid boasting, so it’s easy to downplay ourselves and brush off people who are giving us clues about what we might be good at. Knowing that tendency in myself, I’m learning to say “Thank you!” and examine these things with the same curiosity I want to bring to the rest of life. I ask the universe, “Why is that? And how wonderful can it be?” I can also ask myself.


Thinking about wild success

The more I explain this 5-year experiment to others, the more I understand it myself. =) I thought I’d spend some time thinking about what I wanted out of experiment and what wild success looks like, so that more people might be able to help me along the way.

I think the period of five years because it usually takes about that long before a business can be solidly established. Shorter, and I might mistake the fluctuations of figuring things out for long-term difficulties. Longer than that, and I might drift aimlessly without self-imposed goals or deadlines. Telling myself that I’ll take a close look at where I am and reevaluate my decisions in five years means that I can plan and budget for a fixed time period. Controlled uncertainty.

So where do I want to be on February 19, 2017, the 5th anniversary of starting my own business? What do I want to be able to say? What do I want to have done? Let me fast-forward to my future 34-year-old self and think about what that blog post might look like.

Here we are, five years after I started. I’ve learned a ton in the last five years. It turned out that making things happen isn’t anywhere nearly as scary as I thought it might be. I’m looking forward to bringing even more awesome ideas to life.

I’ve been so lucky to start with something that people immediately wanted and needed. Through consulting, I was able to help people take their businesses to the next level. I worked with amazing people who not only helped me take advantage of my skills and experiences, but also helped me develop new skills. We successfully transitioned all of my responsibilities, and they’ve turned that work into wild successes of their own.

Consulting allowed me to self-fund further experiments. I shared opportunities with other people, working with virtual assistants and other team members in order to get even more out of each day. In the course of training them to take over many of my processes, we built an operations manual that makes it even easier to bring new people on board. Many entrepreneurs’ growth is limited by their ability to trust and delegate, and by the network of people they have. Although I’ve also had my share of rough relationships, I’ve had the pleasure of building an amazing team with skills and passions that complement my own, and I reached out to an even wider network of people I can help and who can help me. Many of the people I’ve worked with have grown their own businesses into something they love doing.

Although I was tempted to continue consulting because it was familiar and comfortable, I eventually pushed myself to try other business models. I learned how to validate business ideas by talking to people and prototyping concepts, instead of simply building something and hoping people will come. It was also tempting to continue with the first new business as a job, but I pushed myself to grow out of it, bringing other people in so that they could make the most of those opportunities when I learned even more about creating businesses.

I learned so much along the way, and I’m glad I’ve been able to put them together in different books – at least one for every year of my experiment. I’ve shared what I learned about networking, productivity, delegation and automation, visual communication, entrepreneurship, business, and making things happen. Taking notes along the way really helped, and so did pushing myself to have interesting and novel experiences. I’m glad that so many people have found the books useful, and I’m sure my parents get a kick out of seeing me in print.

I’m now much more comfortable with reaching out to people and inviting them for lunch or coffee. I always learn lots of things in the conversations, and following up has become its own pleasure. I even host events so that I can bring people together.

In terms of paperwork, my attention to detail and comfort with numbers really paid off. The accountant helped me keep all of my books in order, and the CRA auditor found it easy to verify my records.

In my personal life, I continue to be the luckiest person in the world. W- is fantastic, and home life has somehow managed to keep getting better and better. We’ve got a solid financial foundation, and are excited about the possibilities.

What do the next five years hold for us? I’m not sure yet, but I’m sure it will be a good adventure.

My future 34-year-old self on Feb 19, 2017

We’ll see how it goes!

Rails pub night

I had tons of fun at the Toronto Rails pub night. Met some really cool people. =) Pictures to follow. Finally got to listen to Joey de Villa (The Accordion Guy) play, and his stories about the perks of accordion-playing were absolutely hilarious. Also greatly enjoyed chatting with the other Rails geeks there... =) Totally, totally cool.

I love going to events like these because I not only get to meet interesting people, but I also understand more about the social and technological space we work in.

From the experiences of others, I also learn a little bit more about what _I_ want to do. I'm starting to realize that my ideal life isn't one of teaching within the four walls of the classroom or the four/five months of a term. I want to be out there, teaching really diverse groups of people: schoolkids, seniors, entrepreneurs, volunteers. I want to help people discover how to make the most of technology. It isn't just about teaching, either. In the process of helping people discover something, I learn more about their needs and opportunities for technologies to adapt to people (instead of just the other way around!). That's what I love about the stuff I'm doing at IBM. It's not just data crunching and visualization. I'm there because I'm excited about trying new things _and_ bridging the gap for other people. That requires speaking and writing skills, yes, but that also requires deep listening skills, and I hope to learn all of those really well. =)

If I'm going to go down this path, then - training, teaching, mentoring, coaching, what-have-you - I'll need more experience in order to have more things in common with the people I want to teach. For example, I care deeply about encouraging people in developing countries to make their own opportunities, start their own business, build interesting and useful things. If I'm going to help people create opportunities, then I should immerse myself in the culture and experience here so that I can share those things with them.

That sounds like a plan...

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Random Japanese sentence: すると、ねこが一匹もいなくなっていました。 They could not see a single cat! Suru to, neko ga ippiki mo inaku natte imashita.