Which is It?

I have been incredibly contemplative the last couple of weeks.  This happens a lot when I teach- I get to thinking about how I would design my life, if I could do so deliberately and purposefully.  I am starting to recognize it as a symptom of when I feel like I don’t have choices.  Also, I can be just as big of a procrastinator as anyone else- so conveniently, these contemplative moments happen when I am supposed to be grading or reading papers or prepping for class.

In any case, I have been thinking a lot about what keeps people from accomplishing the things they want.  I read The 4-Hour Workweek  by Tim Ferriss a while  ago.  At the time, I was working in state government and was really frustrated with his ideas.  Long story short, he advocates outsourcing everything possible in order to free up time.  I thought it was highly unrealistic for people like me (people working in places where they have little control over their work life).  But, I am starting to realize that he’s right about some other stuff.  Mostly, that people do a bad job estimating what they actually need in order to accomplish dreams and live their biggest and best lives.

I think that if most people took a long hard look at their life lists and bucket lists, they would be surprised about how much of it is doable.  See, according to Ferriss, the things that most people are putting off until they retire or until their kids graduate or until whenever, are actually doable before then.  It’s mostly just a matter of figuring out what it is that you need in order to do the thing.

On top of that, if you don’t hate your job, you might not be looking forward to retirement (obviously, this is a very bougee thing to say-I recognize the relative privilege that allows me to be able to say that some people don’t hate their work).  While I don’t doubt for a second that there are people who want to win the lottery so they never have to work again, a lot of the rest of us don’t hate our jobs.  If you are a person predisposed to hard work, you might THINK you want to lay on the beach for the rest of your life.  But what happens when you get tired of doing that?  Beaches are kinda boring, once you’re past the thrill of being on a beach and your friends/family still have to work.  So what is the point of working your ass off for a pile of money so that you can retire and lay on a beach, when the rest of your friends and family are still working or in school?

It is easy to think that you need to just become a millionaire and then you can retire and start checking things off your life list.  Alexander Heyne notes that “breaking free” of the “rat race” isn’t likely to ensure your eternal happiness, because often, we don’t have a good read on the situation.  In the end, we have these big goals and life dreams, not necessarily because we WANT to actually do them, but rather because we aren’t really honest about WHY we want them.  With the exception of things that actually require vast sums of money (like buying a fancy yacht or donating a pile of money to charity), many of the things that we want to do don’t require a lot of money.

Time?  Yes.

Knowledge?  Yes.

Logistical support? Yes.

But not necessarily a pile of money

In the last couple of weeks, I have thought through the kinds barriers that people face to checking items off their life list.  And here is what I came up with:

Most of the big things we want require logistics, knowledge, resources, and/or time.


For me, things clicked when I stopped thinking in terms of “When I retire…”and more in terms of “Which of these can I do now?”  Literally, nobody has time for that.  I got things to do NOW.  I don’t have time to wait.  None of us do, really.

There are different reasons why I haven’t done all of the big things I want to do, like hike the Long Trail, learn to ice skate, brew my own beer, and run all the bridges in Chicago. Hiking the Long Trail requires 3 weeks off of work and a commitment of some resources.  Learning to ice skate will require that I have my life arranged in a way that I can commit to showing up and practicing how to do it, maybe hiring a coach, if I needed it.  Brewing my own beer requires a little equipment (most of which I have) and a lot of knowledge.  Running all the bridges in Chicago requires time and a daily commitment- but not a pile of money.

All of us are capable of starting where we are, once we know what we want.  The question is, what do we need to get there?

Knowledge?  If you want to learn to speak another language, are you currently not doing it because you don’t know how to get started?  Should you try an app or local classes?  Should you find a tutor online?  What way of learning a language works best for you?

Logistics? If you want to run a marathon, but are currently caring for a young child or an elderly parent, what do you need to have in place in order to get training runs in place?  Is it a matter of getting a treadmill for your basement?  Or do you need to arrange your days so you can run in the morning before your spouse goes to work?

Time? If you want to write a novel, is it just a matter of carving an hour out of your day to write?  Is there a way to reclaim some time in your day that you can repurpose for writing?  Or would upgrading your phone allow you to write while commuting on a train to work?

Resources? If you want to own your dream home, is it really being able to throw a stack of money at a realtor?  Have you considered the different paths to home ownership?  Is it matter of buying the perfect home or could you buy a fixer upper? Is it only the perfect home in the perfect neighborhood in the perfect city?  Or would you move anywhere?

All of these are questions we should be asking ourselves about why we haven’t done the big things on our lists.  Once you’ve answered the questions, you’re ready to start.