The best laid plans

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Aaaaaah plans. I have had a real push/pull and love/hate relationship over the past 10 years with planning and plans. I will confess - I used to be the type of person who wrote everything down in my diary, and if it wasn’t in my diary, then it wasn’t happening. While I still need the visual reminders to keep my life in order, and to ensure that I make it to the things that are important to me, my experiences over the past 10 years with plans, as I have taken on more complex projects which have some reliance on external factors, have taught me 2 big lessons about the best laid plans.

The first is that things probably won’t go according to the plan. This is the type of things that people often say in a very flippant way but the truth is - it took me a long time to believe it, longer to accept it, and even longer to be ok with it and realize that it might be a blessing rather than a curse. I used to take it personally when things didn’t go according to the plan. I figured that I needed to work harder, to plan better, to have more contingencies in place, to do more things myself, because then I had more control over the situation. And if things didn’t go according to the plan, then something was either wrong with me, wrong with the plan, or both. For years, I tried to plan better, to be better. And when I got to the end of a project, I would make a list (mental or real) of how things didn’t conform to the plan, so that I could plan better next time. I would beat myself up over the things that went wrong, and I was so busy doing that, I never realized the successes I might have had, or the fact that despite my best intentions - things NEVER went according to the plan. I would set goals that were smaller and more doable, just so that I could say that they went according to the plan and I stayed away from huge goals, with lots of moving parts that I couldn’t control.

It is possible that I would have continued in this way for the rest of my life, but there are two things that happened as the decade progressed that have changed my opinions about plans. Firstly, as fate would have it, I spent a year as the president of the Optimist club that I volunteer with a few years ago. The Optimist Club is a service organization that works with youth, and their members “work each day to make the future brighter by bringing out the best in children, in their communities, and in themselves.” I joined the Optimist club when I was feeling the pull to be more involved in voluntary work in my community, and it has been one of the best decisions I have made over the years. I enjoyed the projects that we planned and executed, and I jumped headfirst into taking part as much as I could. And a few years into my time at the club, I was nominated to be club president. I was pretty resistant to taking on this position, as I had seen how stressful it had been for some of the presidents who had been there before me, but the club members assured me that I could do it. And I did.  

There is much that I could say about that year, but for the purposes of this blog post, I will tell you that I finally was able to absorb these two big lessons about planning that year - the first being that things do not go according to the plan. AND the second - that it will be ok when they don’t (and often it will be better than ok). This was probably the first time that I was overseeing plans for projects with numerous moving parts, that depended on several people doing their part in order for the project to be successful. I will say that managing people is a different kettle of fish to managing processes which I had done up to that point. And managing volunteers has the added layer when you are juggling people’s schedules with the time that they are making available for the projects, which might not be convenient for all parties involved to meet at the same time. In addition, I spent a few years in the club, participating in projects, and thinking in the back of my mind how much better I would/could plan it. So this experience was exactly what I needed to knock me down several pegs, as I realized that I could not control everything, and that success is not dependent on everything going to plan. This important lesson fed into the first lesson I wrote for this series - How I finish what I started - as I learned how to navigate the plot twists that life and other projects throw at us, and still manage to finish and get a result which (in this case) resulted in funds raised, children smiling, and new skills and lessons learned. They don’t call us optimists for nothing!! 

Being ok with the fact that things almost never went according to the plan allowed me to finish my own larger projects, such as making progress on this blog, publishing my book, and facing the next big challenge that I had in the last decade - fracturing my ankle almost 2 years ago to the day. That was definitely an unplanned event, and it brought me other lessons such as dropping my habit of attempting to do and control everything myself (there is nothing like needing help to do everything from showering to making a cup of tea to make a person understand how to ask for help!) 

These two events taught me many of the lessons I have spoken about previously, including redefining failure, learning how to get back up after a fall and move forward, and how to make room in my life for magic once again. I wrote an entire post about this here, but I will include some of it below as well. After I fractured my ankle, I hit a real low point, as I entered the new year with only one goal in mind - to regain my independence after a couple of months of being unable to walk, drive or work. I also had an old injury in my hand show up as I tried to use my crutches, which meant I even struggled to write. I was disheartened from the giant comma that this event had put into my life, and for the first time in a long time, I didn’t make any new years resolutions, or goals. I started the new year with no plans whatsoever. 


It was here that I would learn my second big lesson about the best laid plans which is that sometimes when we plan things too rigidly, we miss the magical opportunities that are available to us, if we were willing to make a detour. As someone who had always been a planner, I saw any deviation from the plan as a failure or problem to be reigned in. So-called “inspired actions” were not going to happen if they weren’t in the diary. And if you had asked me a few years ago what I thought would happen in a year that I didn’t have any grand plans, I am pretty sure I would have said - nothing will happen except that a year would pass. I might even have repeated to you this saying widely attributed to Alan Lakein - “failing to plan is planning to fail.” 


By the end of that year, I had written two books, and was well on my way to self-publishing one of them. And one of them was a novel - something I had wanted to do since childhood (and attempted doing several times, without ever getting past page 20). I continued blogging, and managed to write almost 40 posts over the course of the year. I also completed my physio and returned to walking, driving and working. So many things happened that year that I could not have predicted, or even planned for. Things I didn’t know I could achieve or afford. The crux of this lesson was that sometimes when I made plans - I was missing out on the opportunities that I could never plan for - the spontaneous encounters, the inspired action… The magic. Having a schedule that was wall to wall with plans and the actions I needed to take to achieve them left no room and no way for the magic to catch my attention. 


I don’t see anything wrong with planning. Obviously. And it is a great way to achieve so many of the things I dreamed about and bring them into reality. But I also wonder what opportunities I miss when I am laser focused on my plans. And this isn’t about FOMO or regret, I am just genuinely surprised at what I was able to pull off when I had nothing planned. And the thing about planning and setting goals for me – even big goals – is that I feel as if I am limited by my own imagination, by my ability to only plan within the realms of what I believe is possible. And limited by my idea of what I can afford. I honestly was a firm believer that failing to plan was planning to fail, and maybe it is in some instances. But what if it isn’t? What if leaving space for adventure and inspired action can lead to fantastic and beautiful places? I think back on a number of the unplanned detours I made, and I had some of my best times and met some tremendous people. And don’t get me wrong – these things required action on my part too! But it is just a new point of view that I am thinking about at the moment.


I am sorry that I don’t have the answer for you – indeed I don’t even have it for myself. I am just putting this out here – what if we left space for magic? For inspiration? For adventure? What if we took inspired action? The road less travelled? Said yes to the things that we weren’t sure we could afford because they made our hearts sing with joy? What if…

(you can read the full post here)

So these were the two big lessons I learned in the past 10 years about the best laid plans. Do I still plan and set goals? Yes I do! Aside from the fact that it’s a hard habit to break, I definitely think that it is a good way to ensure that I achieve some tasks that I would otherwise put off, and there are always tasks that I need to do (and that I have no desire to), and so I must plan them. But I also hold less firmly to plans these days, am far more likely to roll with the punches when things don’t go according to the plan, remembering that sometimes it is more important to get things done, and that even when things don’t go according to the plan, they almost always work out. And lastly - I spend as much time looking up and around me as I do with my eyes on the plan, so that I can catch sight of magic when it is trying to get my attention, and some days go off on unplanned adventures.

What about you - what is your relationship with planning? Are you a strict planner or more of a go with the flow type? Or like me do you hold loosely to your plans and leave space for the spontaneous? I would love to hear from you in the comments!

And I send you big love from a small island.

PS the photo above is one I took when I was delayed one morning in Bridgetown, and it was amazing. I almost never see that bridge up! These are the bridges that our lovely capital city was named for, and for me that was indeed magic.