On Keeping a Lofty 'To-Do' List

One of the things I’ve picked up from the other, wiser people than myself who are interested in self-motivation is that it helps to keep a lofty to-do list which covers high-level or long-term goals. That way, you’re constantly reminded of how you’d like the future to be.

Back in 2011, I worked at a small digital creative agency called Thin Martian as a junior web developer. It was the very beginning of my career in Tech, and I was (and still am) constantly seeking advice and good ideas from people more experienced than myself about advancing my career and improving my life.

Like in many creative agencies, there was a huge amount of work to do, and tight deadlines. My boss at the time, Damian Gilbert, and I were working quite late at the time and so we had a bit of down-time involving company-bought pizza from The Yard in the evenings. One evening, over a delicious fried-egg-topped pizza, I asked Damian how he keeps so motivated to carry on when times are tough.

One of the thngs Damian told me is that before he started his career as a professional football player (which somehow led to being in tech - it’s a long story), he set out some dates in the long-term future as milestones, and various aspects of his life which should be true at those times. He wrote all this down in a document somewhere. No particular format, just a simple plain text file will do - and put it somewhere he could access pretty much any time.

The long-term dates were things like “on my 25th Birthday,” or “July 2012,” or even further away… 40th Birthday, and so on.

The goals were varied. First, there are the career goals. He said that he hoped to be earning certain amounts of money by certain dates. He made goals for levels of responsibility or job titles that he might hope to have.

On top of that, he put personal goals. Goals for where he’d like his relationships to be at certain times of his life, such as marriage, and children, and friends which he spent his time with. Where he was living, whether he was renting or owning, debt, and other aspects of personal finance also featured in these goals.

Damian told me that although these goals are things he’d be aiming to achieve by their milestones, they should be primarily used as motivators. They should be reminders of what the long-term aims are.

Damian told me that every now and then, he looks at his list and re-assesses how he’s doing. He might’ve failed to reach some goals, or not quite hit targets, but they are a constant motivator.

After I heard this, I could immediately see the benefit, so I set about writing my own list. I keep mine in Google drive so I can add to it. Let me give you an excerpt from my first-ever milestone.

By 08/09/2011 here is where I want to be (I will be 23)

• In a flat with a living room, sharing with at least one person and to get on well with all my housemates
• In a serious relationship with somebody I see at least twice every two weeks
• Earning at least £24,000 p.a.

When I reached that date, I crossed off the first one and the last one. I was very proud of myself. Sadly, the second didn’t work out by that time.

The point is, these were the things which were important to me at the time. I wanted to have a comfortable living situation, a friendship group which I was happy with, enough money to live in London on and I was quite keen to have a serious girlfriend.

I’ve evolved the method slightly over the last couple of years. Now, as well as these milestones I have a list of large-scale or long-term goals to just to ‘at some point.’ When these feel like they should be higher priority, I move them under a milestone somewhere.

The size and themes of these goals vary greatly. For example, one of them is to make a wooden scrabble set, because I’d like to improve my woodworking skills and it’d be something to be proud of. Another is to run a Hack Week at Huddle, because I’d really like to encourage more innovation within the Product Engineering team.

I now keep a tab open in Chrome, pinned, with my to-do list in it, most of the time. Every now and then I look at my list and re-assess how I’m doing. Sometimes I realise I’ve done something, and cross it off my list. Just before writing this blog post I realised I’d achieved one of my long-term goals which I put into the list last year:

It is a small goal for many to get something they’ve done onto the iOS App Store, but for me it was a big deal. Now, I can set larger goals, such as turning a profit with StreetScout, or reaching a certain size of user base.

I’m going to leave that striked-through item on my list, so that every time I look at my list, stare at unfinished tasks, and think to myself, “how the hell am I going to do that?” I’ll be reminded that I overcame a relatively big hurdle once, and managed to achieve a new level of side-project involvement. That reminder will tell me that I can do it again, and again, and again, and each time the goals will become bigger and scarier.

Heckle me on Twitter @basicallydan.