5 Experiences You Need

My career has been shaped by 5 core experience types. Perhaps those just starting out can get something out of these reflections.

I’m fortunate to have held many jobs over my lifetime (actually, growing up, I was “encouraged” to earn money). Fact is, things like shoes and gas cost money. I’ve held the following jobs in my short life (things that the Social Security Administration would know I’ve done…):

Farm worker (corn picker, potato grader, possibly not-so-legal farm truck driver)

Lawn mower

Roadside watermelon salesman

Retail sales associate

Ice delivery boy




Material handler

Loan processor

Investment analyst

Professional athlete

Production planner

Financial advisor

Cold caller



Venture capital analyst

Management consultant

Corporate strategist

It’s a lot.

Now, before you say what a friend of mine said last weekend—”You sure have kicked around a lot in your career,” you must understand that necessity is the mother of work. I grew up with a healthy ambition to play sports coupled with limited sources of funds. The seasonal reality of the sports I played meant that I would cycle through work and sports in a periodic manner—finding a new job every few months through high school and during the summers in college to keep money in my pockets.

I’m blessed because of it; it gave me perspective. So I figured I’d share a reflection on what I think are the best experiences I’ve had from that long litany. I don’t mean the best in terms of my resume—I mean the best in terms of roles that taught me how to want to be a better professional.

I’d argue that these are 5 experiences that you need in order to grow as an effective but empathetic professional.  This is all, of course, one man’s perspective.  They are:

1. Sales. Any kind of sales

You haven’t really lived until you’ve cold called. As a relative introvert (when it comes to work style), I absolutely hated the notion of reaching out to people by phone or door to door, but  I also got a lot out of having had to do so. Once you have called on people and endured a healthy, consistent stream of rejection, you learn that being an A student really isn’t worth much in the real world. The real world is messy.

It’s also healthy to have had to sell things that are easy to sell. I was fortunate to have had the opportunity to sell watermelons roadside during part of one summer in my teen years. It was a product that sold itself (although it never hurt to break open a melon and give people a taste).

As you get older and/or as selling gets more intricate and complex, the experience you gain from selling early on—the experience of influencing and dealing—becomes valuable in every environment. I’ve never seen a truly effective CEO who had no sales in his DNA. Do it. Sell something.

2. Personal service of any kind

Waiting tables is an example of a formative experience that anyone should have. When you provide a service in real time that people will reflect on, assess, and compensate in real time, you become attuned to other people in ways that I’m not sure you can find elsewhere.

There are all kinds of personal service jobs that fit here, ranging from the elite (concierge) to the important but more menial (shining shoes). What they have in common is the need to live up to another person’s standard at least once in your life. The value of that empathy, even if it’s merely learned and not intrinsic, is exceptional.

3. Work with a deadline

Having to work until the wee hours or through significant pain to deliver on a deadline is a formative experience. Learning to manage around deadlines as a writer, analyst, consultant, or delivery boy means learning how to assess a situation in terms of resource needs, capacity, timing, and costs.

Deadline work also teaches you to manage pain. Nothing taught me that better than football games. When you play ball, the game kicks off not matter what state your body is in, so you get ready, and you deal with the pain.  I always appreciated what I recall famous football coach Bobby Bowden once said about an injured player of his:

“He’ll be in pain, but we have a ballgame, and pain don’t matter.”

Deadlines can be tough.  Learning to answer the call regardless of pain is valuable.

I’m learning as I age that there are generational differences with respect to deadlines. I’d go so far as to say that there are some age cohorts in the workforce (ahem…millennials) who have, as a stereotype, significantly less appreciation for the urgency and precision that deadlines can demand. When those people mix with others that are more delivery oriented…they lose. Understanding what deadlines are and how to commit to and manage around them comes from critical experience.

4. Work that requires you to write

I first became a published author when I wrote an article entitled “Venture Capital in the Not-So-New Economy” while moonlighting for a consulting firm in 2001. I was volunteered to write a series of blogs (under deadline, surprisingly enough) for BusinessWeek Online while in graduate school, and now I write for fun. I have always found the absolutely necessary habit of stopping, structuring, and thinking when writing to be instrumental to my later career. Clarity of thought is a rare thing—I always strive for it, and sometimes I achieve it. Writing as a job and as a hobby is a fantastic developmental pursuit.

5. Work where there is no safety net

I still have in my file cabinet (somewhere) a two-year contract with the NFL’s San Francisco 49ers. There is likely no more pure meritocracy in the for-profit world than an NFL roster. You either produce, or you are cut. You tend to know where you stand right away, and  I certainly did—I lasted a few preseason games, and I was cut. I “failed.”

But that failure has made the rest of my career a cakewalk.

I spent more than 7 years as a client service staffer (that is, on the tip of the spear) at the world’s most renowned professional services firm. That firm is known as much for its brand and talent as for its “up or out” career development policy. There was, once again, a distinct feel that you either perform or you will be cut. While the environment was more humane than the NFL, this model was high pressure. It was a social contract understood by all. It made you sharp, and it created focus.

Once you’ve worked without a safety net woven out of bureaucracy, cronies, and obfuscation, you realize and recognize more and more of the bad behaviors that come from rent seekers and moochers. You also notice the really bad ones—the ones who tell everyone else that it’s a meritocracy while really just politically and financially feathering their nests. Their safety nets start to entangle their morals.

I’ve had the joy of diversity in the work that I’ve done. I’m so thankful that my life circumstances have afforded me the opportunity to work everywhere from a tractor to a delivery truck to a storeroom to a boardroom. I’m truly lucky.

I hope my perspective can be of help to you.

2 replies
  1. Bryant Reeves
    Bryant Reeves says:

    Great blog. Growing up on a farm creates work ethics that are not found in most homes today. I know for I grew up with tobacco stick in my hand and cotton to be gathered before the storm,
    Will forward this to my friends.

    • Geoff Wilson
      Geoff Wilson says:

      No doubt, Bryant. I never worked as hard as I did one early summer loading watermelons with a crew of migrant workers. I can still feel the steam coming off those fields in the early morning. I owe my uncle a lot for that experience.


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