When looking into the future, the definition of ambitions is often intertwined with an assessment of their feasibility. There are two, frequently opposing, guiding principles at work:
- Be who, how and what you want to be.
- The past tells you what works for you and what doesn’t.
The former being a fairly idealistic and empowering maxim, possibly reminiscent of rationalism, I like to think of the latter as Realpolitik on a personal level with a scent of empiricism.
Personally, I feel very drawn to camp 1. At the same time I do acknowledge that there is some relevance to the second premise. There is just something very romantic about defining a goal, constructing an seemingly sensible approach and raising the ambition of executing it without hesitation or compromises.
Romanticism aside, definitions of approaches might come with flaws. There might be unfavorable starting conditions that were left unconsidered. There might be inconsistencies in the deduction of the approach. There might be devastating imprecision in the definition of the goal. All of those flaws can cause an approach to fail, and the past can take on the role of the failure’s witness.
I hope to combine the hope and innocence of premise 1 and the relation to reality of premise 2. Let’s look at an example.
Observation: Whenever I’m with Marc I end up drinking alcohol. I dislike that because the habituation makes me suffer from the downside of alcohol while removing the upside of its enjoyment. Moreover, I’m a bit worried as to what this says about Marc and I’s relationship. 
Goal: Don’t drink while seeing Marc for next half a year.
Approach: I will always bring enjoyable, alcohol-free drinks when meeting Marc. Also, I will voice my intention at the first encounter.
So far so good. Let’s add to that the empirical observation that I somethings figured it’d be cool to drink less. Yet, in such moments, at the latest when being offered a drink in a social setting, I complied and failed to drink less.
I would not want to let this discourage my belief in the execution of the newly formulated approach. I would argue that the vague intention of ‘drinking less’ is not representable for the feasibility of my plan.
Yet, if the empirical observation was that I set out to execute the exact same plan with Ben instead of Marc, I would want to be alerted. I would want this evidence to make me question harder whether there is justified hope to realize my ambition.
The difference thereby lies in the similarity of the situation. Importantly, the notion of similarity should, in my view, capture the explicit consciousness of the task at hand.
Going forward I’ll try to use the heuristic of asking the the proxy that is the following question:
Have I previously, with the explicit consciousness of the situation and its context, attempted to do the same? If yes: Re-evaluate feasibility or redefine plan. If no: It shall be done.
Thanks to Ruifeng for pointing out the following beautiful quote from Claude Shannon :
Thus we may have knowledge of the past but cannot control it; we may control the future but have no knowledge of it.