
I was talking to Ian Ybarra the other day and realized that, although my days and weeks are largely planned out, what about the long term planning? Sure, I can prioritize the little tasks but what about the big picture? Do I know what it is I’m doing and why I’m doing it? Yes and no. Who says I need to?
Timing is everything
On one hand, it’s nice to know what your goals are. Ian made an interesting point: he loves baseball. Sure, he could keep writing and maybe even do some speaking right now but in 50 years will he still be able to play ball? Not likely. Would he still be able to write and speak? Probably. So, if you had the two options which would you choose to do at this stage in your life?
I’m sure we all do the same kind of prioritizing every day. For example, I could sit here and keep working until 10pm or go to the gym now and work later. Given that the gym closes at 10pm it’d be wise to take care of that first. Can I metaphorically zoom out a few weeks, months, or even years and look at what it is I’d like to accomplish given my finite lifetime?
Some people argue it’s best to become an entrepreneur out of college. You don’t have a family and kids to worry about, you can spend an absurd amount of time working and if you fail it won’t be a big deal. On the other hand, if you were to wait and work for a number of years you could build your savings. With more money and more experience you might avoid a lot of hassle and issues that neophyte entrepreneurs would face. Which is the right answer? How do you know when its the best time to do _______?
Living one week at a time
So, as I sit here I realize I don’t have this issue, yet. Maybe I never will. I don’t have lofty goals and I don’t sit and dream about what I might be able to do: I just ‘do’. Similarly, Ben Casnocha says he, too, lives day by day and simply keeps taking on new opportunities. In fact, he cites one of my favorite quotes (remember I have a constantly updated collection of quotes here).
“We have a ’strategic plan’. It’s called doing things.” -Herb Kelleher, Southwest Airlines Chairman
People constantly ask why I take on so many projects, jobs, and so on. I figure opportunity shows up in so many places. By making myself readily available I’m not missing out on anything. Additionally, instead of having to actively look for new things to keep me busy and growing (and employed) I am more frequently approached by individuals looking for someone to help them. The timing has worked itself out; I’m no longer anxious about when and how things are going to happen.
With that said, it seems my strategy of “wandering” is paying off.




Interesting post. With the entrepreneur thing, I’ve heard those same things you mentioned, but I really don’t think there is a right time. I’d just say to do it when it feels right and resources are lined up to get things done.
What’s weird, is that sometimes when I plan hard on things they end up not working out. It’s weird, and has kind of changed my view on planning.
I don’t consider myself a big planner now, and take things day by day. However, I am working on starting a small design shop to do on the side until enough clients/resources are lined up where I can go full time. Would that be considered planning? My own company full time is my long term goal, however I’m taking things as they come.
There is a relationship between goals, how far in the future you are planning, and the certainty of the outcome. For example, my goal is to get coffee after I write this, and then read some technical specifications that are due tomorrow. Good goals, with little doubt about the certainty of the outcome. I plan to become president of the United States of America before my 42nd birthday. Aggresive goal, extreme uncertainty about the outcome, and very hard to write down all the required steps to achieve the goal.
I conclude that short term goals can be planned and the plan executed to achieve the desired outcome with a high probability of achievement. A life-time goal can not be planned with much certainty of the outcome. There are far too many variables outside your control that will influence the outcome.
Last notion that seems to have a bearing on this. The way you define you personal value often falls into one of two main categories – to have or to be. Consequently, the goals of a “have-er” are quite different from the goals of a “be-er”. If acquisition and ownership define you, or experiencing the world and behaving within a framework of moral & ethical values defines you, then the notion of what is a goal changes quite a bit. And the kind of planning you engage in looks very different.
Time to achieve my “have-er” goals of coffee and reading
All good points. J Phill I think you’ve got the point; there may never be a ‘right’ time, it’s all relative. Speaking to what my Dad said I think when it comes to planning you’ll find there are many more variables outside the plan you can’t account for.
So, by removing the plan you’re succecptable to those factors alone. I think your real ‘goal’ should be positioning yourself and preparing yourself for when and if those factors and opportunities ever come around.
Now, would you say that in some sense, it’s point to plan because you never know what variables could change your course of direction? Some variables you can plan for, but some you can’t which seems to leave the plan very foggy, because nothing ever goes to plan.
So is preparation without plan possible?
I guess I’m using the words in different contexts. My point is that a plan is typically a definite course of actions to take. Preparation is thinking what you would do given certain situations. Being prepared (educated, in the right place, know the right people, etc.) is different than telling yourself “I will do this in a year.”
I’m going through a bit of this myself. A friend of mine suggested that one thing I should consider is writing very long-term goals, as if I was writing a retrospective of what I did and feel good about, what my life is like, etc. The idea of writing a story like that is appealing to me for several reasons: for one, I like writing stories and for another, it makes it possible to assess whether things I’m doing right now fit into that plan. Of course the plan can change, and will, but I suspect it would give me something to focus on more than short term tactics. Right now I feel like I’ve been swirling around in very interesting circles.
Hi Dave, it’s great to hear from you. I like the idea of long term goals. Nothing happens without some sort of plan and idea in mind. Obviously I’ve got some lofty goals (retire early, on an island, etc.
). I like the story idea, perhaps I’ll start my own soon. Heck, I write it in my head enough- why not on paper?
Best of luck as you get through your own story.