Life Planning

My Bullet Journal practice helps me plan against different time horizons. Each morning (or the evening before) I contemplate what I need to achieve in the coming day. On a Sunday I’ll think about the week ahead. On month and year boundaries I consider a longer time horizon. But I don’t have a mechanism for thinking about longer-term goals.

Many guides for how to have a good life talk about setting life goals. The Seven Habits Of Highly Effective People has as habit 2: begin with the end in mind. This is all about setting life goals. If you are not clear about where you want to go how will you get there? I don’t know where I want to go through.

Start at the end

I did try as an exercise to write my own eulogy. A eulogy is what is read at a funeral and tells those present about how amazing the person they are celebrating was. I’m not sure where I got this exercise from – probably a book or a podcast. I didn’t complete the task but it was a useful thinking exercise. What would I want to be remembered for? Well, not just a string of promotions at work and certainly not for watching loads of TV box sets (this predated my Netflix subscription).

I was a bit concerned that given I’m typically goal driven (I’m a programme manager at work) I might set a goal and then drive to that and miss out on wonderful opportunities just because they don’t align. I mean who is still doing the job they dreamed of doing as a kid in school?

This existential uncertainty continued until June 2016 when I started to journal. I was 3 years prior to turning 40 and probably the point at which I had to admit I was not in my mid-30’s any more. In my journal, a list I created was: 40 things I want to do before I’m 40. A short enough time horizon that I could plan and a long enough one that anything is possible.

As a side note if you want an approach to ponder what you have achieved with your life and what you might achieve in the coming years have a look at your life in weeks. Be warned it will in part fill you with disappointment at the boxes you squandered and mild panic about how few boxes might remain.

Mid-life bucket list

My 40 by 40 list has small things like camp on Lundy Island and rock climb outdoors (ironically both not yet done). It also has challenges that need much more commitment and planning such as cycling LEJOG, diving in Truk Lagoon, learning to speak conversational Spanish, learning to play my guitar, and developing a location independent career (also all not done). I believe that I can do (almost) anything, but I can’t do everything. So narrowing down the possibilities to 40 was a helpful prioritising constraint.

A quick count suggests I’ve only completed 13 out of the 40 things on the list. I am not even 1/2 was though it after nearly 3 years and now there are less than 100 days to go. I’m deadline driven so all the magic happens just before the end right?. Well, not quite. It’s going to be really hard to go 90 days booze free between now and turning 40 with an extended family holiday away over Easter to celebrate my 40th and my dads 70th.

A couple of things have been delayed by event schedules. I’ll hopefully tick of the full iron man in July so only a few weeks late. And the marathon over Snowdon is in September so that’s kinda close right? I’ve got quite a few that I am on track to tick off. I’ll still fall short of 40.

This is not a new realisation that I am off track with my 40 by 40. I have got through several books with my journaling. Each time I start a new book I copy over my 40 by 40 list. Even by the time I started on my second book, some of the goals were highly unlikely and others did not resonate with me as strongly as they had done. I kept them on the list as a useful reminder.

So I guess we could conclude that, for me, 40 by 40 has been a huge failure. It’s actually been a huge learning exercise. In that lens, it has been a significant success.

Lessons from 40 by 40


I am (broadly) on track to hit my target of completing an Iron Man this year. If I analyse why that is I can see that I set a series of incremental milestones (sprint tri, Olympic tri, 1/2 iron) and planned what I would need to do to get to each. I prioritised my time allocation and enlisted help (a coach). I’m currently pre-committed to the event as I shelled out inordinate sums of money on the event ticket, the flights out there and accommodation. Planning and pre-commitment work. this is not a surprise to me and I’ve blogged about it before but there is a knowing-doing gap.

I contrast this with my camping trip. The plan was to go last summer. All I needed was a weekend with good weather. There were many weekends with good weather. Still, the trip didn’t happen. There was no plan, no compelling data or deadline and suddenly autumn was upon us. Simply picking a date and booking a site would have probably got this in the bag last year.

Goals and proxies

Some of the goals were not about the thing but the thing was a way to capture something else. A proxy. I wanted to complete 100 park runs as this represented a regular exercise habit. Though my tri training I achieved the regular exercise so the park run goal no longer resonated with me.

I wanted to rock climb outdoors. I have done loads of indoor climbing after an initial outdoor climbing taster but I’ve never made it back outside. Just going out for a day and climbing would tick this off but not really achieve the sentiment. This was about spending more time in the outdoors and spending more time with a mate who I climb with.

Ill-defined goals

My 100 park runs goals was overly specific. It gave a metric to measure something related. My goal to be confident completing a full bike service is not SMART in the goal setting sense. I’m happy doing the basics. I find some tasks really fiddly to get right (gear alignment and disk break alignment). I lack the tools and the need to strip or replace a bottom bracket so I’ve not done this. Do I get to tick this one off?

I want to do some wreck research at the National Archives. When I am diving we often dive unknown sites and it is fascinating when club members work to piece together to the history and identify a previously unnamed site. I have visited TNA, I’ve done a bit of research. I didn’t discover anything groundbreaking. Do I get to tick this one off?


I was confident that over three years I could achieve a lot. I did not spend much time prioritising beyond the constraint of 40 items. 

My list has a number of big trips in it (Mallorca cycling, Shetland diving, Truck Lagoon diving, cycling across the country both ways – LEJOG and Sea to Sea [again]). These represent huge chunks of time away from home, away from the family. I didn’t give enough thought as to what was sensible. I also did not discuss enough of the list with my family to get their support and commitment.

Some of my goals had soft conflicts. For the 1/2 iron man last year I was regularly training 12-15 hours a week. Weekends were where I would do my long training sessions. Weekends are where I typically dive since I live a long distance from the coast. My tri training put a dint in my diving so I did not hit my planned 500 dives. So I can’t turn my dive log into the 500 dives photo book I had planned. Next winter I plan to spend some serious time on the computer turning my dive log in to a book however many dives I’ve done. My log is electronic so it’s mostly just a job of sorting out the formatting. And correcting all the spelling mistakes.

Looking Back

If I had not created my 40 by 40 list I would probably not have toured the Canadian Rockies in a huge RV/motorhome. I might not have cycled to Paris. It’s doubtful I would have got my son to climb his first mountain. I would not have thought 3 years ahead to consider what it might take to complete an iron man. The iron man training alone will see me hit 40 in much better shape than I was in at 30. Just for these 4 things the whole 40 by 40 list was worth it.

Looking forward

In the book When, Pink explains how “nine enders” (those who are 19, 29, 39, etc) often make life changes as they approach milestone birthdays. This is why there are a glut of 29 and 39-year-olds completing marathons (and possibly irons man races 🙂 ). When I hit 40 I am looking forward to reviewing the list and thinking about which I want to roll with. I’ve already got a few new things lined up to go on my 50 by 50 list. Go big or go home 🙂


Leave a Reply