The five year plan should be a relic by now

Five year plan

Let me try to get into this idea of the five year plan a little bit dramatically. Bear with me.

I’ve probably been to 7-10 funerals in my life. Last Saturday was No. 10 or so, and it happened to be a good friend of mine who died about 12 days short of his 36th birthday. Death isn’t fun, but when you go to a funeral for a 94 year-old, there’s a sense of “Well, full life.” 36? No.

Before this deal, I’m sitting near Culver City eating a breakfast burrito. “Eating” in this case means periodically putting some of it into my mouth while mostly pushing it around the plate.

The family’s Catholic, and we’re talking about whether it might be open casket for a bit — during the reception/”wake” period, at least. We all concede that it could be.

We finish the breakfast, walk back to the car at our friend’s apartment, and drive over. It was about 35 minutes. The whole time I’m thinking about my friend, his life, our times together, and whether this casket is going to be open.

We get there with about 20 minutes left in the reception/wake period and lo and behold, it’s open at the front of the church.

I had just spent the better part of a half-hour (and a flight the day before) wondering what I would do in this situation.

should go up.

Do I have the strength to go up?

Initially I decide not to go up. It’s too much.

But then a couple of my friends decide to, so I do as well. It seems like I should do this. Pay respects.

I probably hadn’t seen my friend IRL in 2.5 years, and then add the concept of “death” on top of that. It’s obviously not the same. Not what you remember or expect. I lasted about three seconds.

When I turned away, my first thought was:

I was never ever ever fucking supposed to see him like that unless we were both in our 80s.

That was never ever ever supposed to happen.

I had to live that moment I never ever should have. 

Then about 14,883 thoughts entered my head in the span of time from going from that casket back to a pew.

This post is about just one of them.

The five year plan as bullshit, work-wise

We all know the cliche: “We are only promised today. We don’t know about tomorrow.”

When you see an ashen version of your friend in a suit a few feet from you, that one kinda drills home for sure.

Let me hit the work side of this deal first, then I’ll get to personal.

Even if you work for a big company these days, you are promised nothing. Disruption is fairly common. The tech stack has way outpaced people. A good salary? No. Firm-size wage effect has eroded that.

I’ve seen studies that an average company pivots their business model/strategy every 2.1 years. If you’re talking about a five year plan, that would mean your company would be several rotations different in five years.

Oh, and you might not even be there — average North American job tenure presently is 3.6 years.

Most studies also show average employees don’t understand either the (a) strategy or (b) planning of where they work.

It doesn’t seem like this five year plan model really makes any sense in the age of “VUCA,” does it?

But … the “we’ve always done it this way” problem is here

The whole question about your five year plan remains one of the most common job interview questions.

I understand why on the surface: to some HR flack or hiring manager, it supposedly conveys that the candidate is purposeful and forward-thinking.


But what does it matter as a question? 3.6 is an average tenure. In five years this person in front of you might not work for you. Statistically that’s the better bet. So why do you care what they plan to be doing in five years?

Also: any ambitious person that you’d actually want in a role would say, “I’ll have your job.”

Problem: that person would never get the job because hiring is typically based on avoiding threats as opposed to getting the best people. (I hope we all know that by now.)

I hope we all also realize that most interview questions are generic slop fests, but somehow we persist with this ridiculous model.

The personal side of this five year plan deal

OK, let’s try this. Five years ago today would have been October 17, 2012. I have no idea what I was specifically doing but here’s a general framework of what I’ve got:

  • In graduate school in Minnesota
  • In a long-term relationship (engaged, actually)
  • Figured I could be an organizational development type consultant
  • Hoped to have kids by 35 or so
  • Never went to the gym except for maybe 3 times/month to do “machines”
  • Had left NYC that past July so still up with some of those friends
  • Didn’t have a blog

Alright, today:

  • I’m not an organizational development consultant
  • Grad school was good in some ways, but I also have a ton of debt and don’t work in those fields
  • No longer with that girl
  • Probably more known as a “blogger” than almost anything else in my life
  • Not as up with those NYC friends
  • Live in Texas
  • Work out probably five times/week
  • Don’t have kids

That’s five years. In the grand scheme of life, it’s not a ton of time. Literally everything about my life is 100 percent different. And honestly, the girl side and the friend dying side have all happened since March. That ain’t even a year.

Back to this funeral for a second

Before the actual ritual ceremony got going, I’m talking to someone in the pews. Don’t know them super well.

They’re asking me about my life in a way that’s supposed to be small talk but comes off as wanting deeper answers.


So at some point, before we’re about to see this casket proceed in to begin the real deal, he asks me a question like “Think you’ll stay in Texas? What’s your five year plan?”

And I just look to the aisle and I’m like “Five year plan? Maybe we should ask our friend in there about that.”

That was probably the third time that day I started crying. I got to about 11 total.

So what’s my point here?

Personal side: I’ll spare you the empowering “LIve for today!” shit. But really today is all you’ve got. Just do your best and work on yourself. Take care of yourself, love yourself, and lean into the skid periodically. I guarantee you that if you looked at October 2012, you’d see a lot of differences. Things gonna change. Embrace and deal as best you can. Be good to yourself and try to understand where your blind spots are. A lot of people don’t, and social/tech has probably extrapolated those problems.

Professional side: If you evaluate candidates, please get rid of generic questions that prove nothing aside from making the Adam Sandler joke “Not dead” and seeing if it gets a laugh. As an employee/entrepreneur/whatever, realize a lot will change in five years. It’s much more about being adaptable. Most growth and productive work comes from putting in the actual work, not from “hacks.” As long as you keep realizing that work, you should be OK.

I am not saying “Fuck goals.” No. Have goals, beacons, road maps, lights, etc. Just realize that Act II of life will throw you a few personal and professional curveballs. It’s not the actual five year plan that matters. What matters is how you get back off that mat.

Ted Bauer


  1. I like this post in part because I had a lot of the same feelings on seeing him up there. Part of the reason I needed to see him was because it doesn’t feel real to lose a friend at our age and I needed to know that this was all really happening.

    I still think the important lesson in all this, besides what you say about focusing on today, is not to let so much time go by without talking to and seeing your friends. Because you never know how much time you really have.

    Though it still doesn’t feel real.

  2. Sorry for your loss Ted.

    The “five year plan” question is also one of my least favorite elements of hiring practices. I’ve debated people on this topic and generally the defense of the question involves assertions like

    – “it shows how well a candidate can plan”,
    – “it helps identify those who will leave within a year or two, and turnover costs money”
    – “it helps uncover hidden motivations” (literally what some guy tried to put across on Reddit once)

    While I agree that it’s important to find a way to:

    – ascertain a person’s planning skills (IF the job requires them to engage in planning),

    – find ways to get companies to retain talent/employees to stick around (that’s just always going to be more on companies than employees though, companies have far more resources than individuals and thus far more influence over a work environment/workplan), and

    – not hire pathological liars (I guess that’s what he meant by “hidden motivations”? I think he may just have been a pompous corporate douche who thought his brain had a built-in polygraph),

    These, of course, are all points that can be argued against; unfortunately, many people confuse opinion with fact, seem unwilling to consider another viewpoint, and haven’t had to show their work since math class in the sixth grade.

    Asking someone what they see themselves doing in a completely arbitrary time period is a really inefficient way to gather that data. First, it’s too broad, and in its excessive breadth can produce information that’s irrelevant/can get companies in trouble (depending on what the candidate shares). Next, as you’ve pointed out, any answer is going to be entirely reliant on certain contingencies falling into place that no one person can have complete control over. Finally, there aren’t any safeguards to protect against a canned/complete bullshit answer. There are websites upon websites that provide job seekers with ideas—or rote responses—for how to answer the question that would please most hiring managers/HR types.

    Of course, there are all the concerns this question raises related to confirmation bias, subjectivity, firm-size wage effect, etc. I don’t need to reiterate all that, you’ve done a great job elucidating those issues here.

    As far as my last five years go? Shit, I was living in New Orleans unloading trucks five years ago today. I didn’t plan on returning to grad school, didn’t know if I wanted to stay in NOLA or leave (certainly wasn’t considering living in Minnesota), had just started dating my soon-to-be wife, and didn’t really know if I wanted to continue working in nonprofits. Hurricane Sandy, family issues, trying to establish work-life balance while affording an apartment that wasn’t a walk-in closet as a nonprofit employee in NYC, and the bonkers nature of post-Sandy-disaster-recovery in NYC changed all that quite dramatically.

    For that matter, my job here in Minnesota has changed quite a bit in the 2.5 years I’ve been at my org. I came in as a part-time accounting assistant, was given a full time job and took on some HR duties, now I’m being shifted into higher ed project management under a different supervisor. We literally shift direction every four years under our strategic planning process, and our last strategic planning process produced an organizational re-structuring and job redesign for several people. The five year plan question is frankly useless in the nonprofit sector, come to think of it, as conditions/funding are subject to rapid change; a nonprofit itself can be “out of business” in that timeframe if a few grants are lost or funding declines.

    I think a better way to approach gathering the data the question is supposed to produce is to be frank with a candidate about WHY you need good long-term planning skills/someone who’s willing to commit to a long-term relationship with the organization/someone who has a sound understanding of the issues an organization faces and a reasonable plan for how to achieve them. Specificity in these areas can generate more organic conversation and provide better information, and I believe an informed hiring manager is a happy one.

    A while back I wrote this thing on LinkedIn on this very subject that was inspired by something you wrote: https://www.linkedin.com/pulse/five-year-plan-question-use-wisely-dont-all-dan-darbandi-cppm/

    Cheers and hang in there


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