I feel like the “Five Year Plan” is everywhere–it’s the new thing in personal financial planning (according to some bank’s commercial). It’s the subject of a common job interview question. China’s been in love with 5-year plans since the Mao days.
I can see how it would be a useful personal development tool and a way to make sure you’re living your dream life. Putting anything on paper helps to identify goals and create a visual map to achieve those goals. Since I really like lists and schedules as a procrastination avoidance technique, the 5 year plan idea sounds good.
Many personal five year plans have you work backwards. You identify where you want to be or what you want your life to look like in 5 years’ time, then fill in the intervening time with the things you need to do to get to that place. Highly logical.
It’s also a bit intimidating. I think as humans we have a nagging consciousness of how life can come in and screw with us and our little plans. So making goals years in advance can present a scary prospect–what if we fail, on our own or because of some unforeseen event?

Unforeseen... like hitting a moose? (no joke, my husband hit a moose last fall. He was fine, thankfully!)
So I am also intrigued by the idea of working the opposite way. What if you focus on things that make you happy and see where that takes you?
For me, it might look like this:
- classes or coursework in writing, computer stuff, homemaking/cooking, interior design/decor (clearly education is an ever-present option to me)
- yoga instructor training
- lots of travel and maybe a stint living abroad
Where might all of that take me? Perhaps to a Thai island, running a guesthouse where I offer yoga classes and travel services (and there would likely be excellent writing material from that scenario). Maybe some kind of freelance writing for the internet. Perhaps opening a lifestyle and home decor store.
I understand why the Planners work backwards. It could be dangerous to just say, “I’m going to do whatever I want right now.” It would be tempting to act with no consideration for the long-term consequences.
However, keeping a general goal of happiness could be a check on that. You won’t be happy if you’re broke or alone.
Prioritizing happiness creates accountability. It doesn’t make me happy, really happy, to eat lunch out every day. It does make me happy to save up to have a special meal with my husband that we’ll always remember.
Just look at my jars. Even the most money-averse of us can be financially responsible. If I decide I really want to take a course in one of those things I mentioned, I’m sure we would be able to find the money. With discipline, you just make it work.
I suspect that some people will much prefer the goal-setting method, not being comfortable with big unknowns.
For me, I know that I get bogged down by self-doubt and end up not starting something because I’m afraid of failure. Instead, when I just start moving on something, I end up surprising myself with both the enjoyment and my success (it’s the perfectionism-procrastination theory magnified).
Ultimately, a combination of both approaches would probably be most successful. It’s important to set goals. But it’s also important to be flexible and realize that life doesn’t always go as planned, like my mom said.
I don’t want to be intimidated by the prospect of not achieving my goals. I want to be inspired by and excited about the unknown future.
Which side do you think you fall on? Do you make 5 year plans, something like it, or have you found another method for finding happiness?
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“What if you focus on things that make you happy and see where that takes you?” + “when I just start moving on something, I end up surprising myself with both the enjoyment and my success” = my view exactly
Judging by the design elements you have interspersed…design may be in your future…perhaps not literal design…but a type of design…instead of teacher/instructor/professor, I like to think of myself as an instructional designer.
“Instructional designer”–I like that! Thanks for commenting 🙂
I love this post Jean! 🙂 It finally highlights the other side ( i.e. NOT setting a 5 year plan). Being a planner type person myself, I always set 1, 2, 3, 4, 5 and even 10 year plans. While I have achieved some things that I set out to achieve, there are many things that I haven’t and THAT (go figure) bothers me the most!
Life for me took another route (marriage, house), which is far better than I ever imagined, but it has also left me wondering about the goals I didn’t achieve (re: my career and grad school). As a result, I kinda don’t want to take the planner route anymore. I prefer to do things that make me happy, or that I enjoy now and see where it leads. ….Yes, it scares the crap out of me, but then again so does setting out to do something and not coming close to achieving it! (It’s like a “to do list” that can never be checked off!)
Thanks for sharing your experience! Yes, I also get frustrated when I can’t cross things off the list (big or small). I love your insight about your off-the-plan route being better than you could have imagined. I feel the same way about it. I find it helpful to focus on those sorts of experience to remind me that the “unknown” is worth being excited about!
This is so timely for me, because I attempted to start a 3-year plan last week (notice “attempted” – I haven’t finished it as I also suffer the perfectionism-procrastination phenomenon). I’m so glad I read this post before proceeding, because I was doing this from the standpoint of looking at the perfect future 3-year self, and backing into how to get there. I like this so much better, because what was scaring me about working backwards is the thought that kept haunting me: what if I’m not here in 3 years? (or my husband, my home, my job, etc.) Thanks for the insight!
Funny that you were just working on this whole thing! I’m glad my post made you feel a little better about the whole process. I think the key is just being flexible and confident that if you work on start from what you know makes you happy, things will fall into place. Good luck and thanks for reading!
My general rule of thumb is to stay away from anything the Commies thought was a good idea – so I’ve never been a fan of 5-year plans. 🙂
Hahaha, not surprising…