No Longer Cheap: Jobs-to-be-done Made Me a More Confident Buyer

My default used to be “don’t buy it”. Now, my default is: “buy it if I can feel the push for progress”.

I used to hold prejudices about selling and commerce. That changed when I decided to learn from people I knew held values close to my own, but didn’t have those prejudices about money.

They used Jobs-to-be-done, and so I decided to learn about it too. With it, I learned how to sell in a way that was considerate and patient. I then learned how to buy.

Learning to Sell Right

Ryan Singer, Jason Fried, Bob Moesta, these people didn’t look like the salesmen against whom I held prejudices. From them, I learned how selling is about being of service.

I used to hold prejudices like the following…

  • Selling is about convincing and manipulating;
  • Sales are inheritently extractive;
  • People only buy under pressure.

There’s a different way to see things:

  • A sale can be a considerate exchange, where both parties come out benefiting;
  • Great sales experiences start with having empathy for the buyer;
  • A buyer just wants to make progress, to get away from the old, and get closer to what’s next.

That’s the essence of the Jobs-to-be-done theory. People want to make progress. They’re “hiring” a product for a “job”. They aspire to get ahead, get to the next step, be seen, be heard, be important, break to the other side of the wall, make a difference for someone.

That also means that most people you come across aren’t in that rare moment when they’re ready for making a change, for making the switch. No use being in sales mode.

Most of selling is best not spent in sales mode. Most of selling is best spent listening. One buyer you can start listening to, is yourself.

Learning to Buy: Looking for the Push for Progress

You can try to be rational about your purchases. The benefits outweigh the cost. Pros and cons. “It’s a rational expense.”

But it pays to listen to the mess of feelings that push and pull in your mind.

If I buy this, I’ll be able to…

That hints that you have a deeper aspiration, that you sense a utility to help with something bigger.


There’s a sale going on right now, I’ll get it for cheaper…

Careful, that one’s about amassing things you might not need. Listen to what’s behind the appeal, but be wary of the pressure that discounts create.

But I don’t want to have to deal with these aspects of the product…

That’s an anxiety about the product. Totally legitimate. Lazy products have un-reduced anxieties. Products worth buying make sure the ramp-up is smooth. Keep your standards up.

That’s expensive, but I want it…

That one’s interesting. That’s a sign you want progress.

Enough is enough, where’s that thing I saw the other day?

This. That’s when you know there’s a struggle. There’s a strong push for progress. That’s what I’m looking for. That’s when I know it’s time to buy.

Examples of the Push for Progress in My Recent Purchase Deliberations

Here are four situations that ended up in a switch, in a “hiring” of a thing for a “job”, in progress being made. However, not all of them were a switch to the thing I was considering buying…

  1. A few days ago, I upgraded to the Family bundle for Apple Music. I was struggling with having deep, long stints of concentration in my work. There was anxiety around using our Apple Music subscription to get “in the zone” at my work, for fear that someone else in the house might press Play on their device and my music would stop. But an “enough is enough” moment got to me, and I wanted progress on getting “in the zone” at work. A few bucks a month for the Family bundle would allow all of us to listen to music at the same time. That did the “job”. Switch.
  2. Last year, I bought Bullet Train, a Ruby on Rails starter kit. A friend of mine asked if I could build an application for his startup. I wanted to find a way to offer him a fixed price. Bullet Train allowed me to spend a portion of that fixed budget (it was a “good” portion of that budget) so that I could save a bunch of development time and increase the quality of the app by having a bunch of decisions already made. I “hired” Bullet Train to win a client, to up my client and coding game. Switch.
  3. A few years back, we didn’t buy a bigger house. There was a lot of excitement at one point, but I was wary of not having a good sense of the progress we wanted to be making, my wife and I. There were other ways we could address our struggles, for much smaller investments of time and money, that did the “job”. So we made progress choosing those smaller options instead. Switch.
  4. Last year, I bought a email address. It came after having tried ProtonMail for a while, in a move away from using Google services. So, in a way, the struggle I had been feeling around “when you’re not paying for the product, you are the product” had been solved. But I was still feeling the struggle about managing my attention around email. I hired HEY for the job of giving me back some of the attention I had at my disposal every day. Sure, the price was an anxiety. But ProtonMail’s standard inbox+filters approach didn’t address that anxiety for pretty much the same annual price. Plus, with HEY, I could get a short, easy-to-spell address. Plus, I could be among the first ones using this cool new thing. Plus, and this was only felt after the purchase, I restored a fraying connection I had with the good old web. Switch.

Switch. That’s what happens when there’s a push for progress, and a sane purchase is made.

Studying Purchase Stories

When you’re studying your own purchase deliberations, you’ve got an advantage. You know the full story.

If you’re researching your buyers, to try to get a sense of what made them switch, you can do the same with them. You can ask their purchase story. To perform an effective purchase interview, you have to ask a specific type of question (retroactive questions), but you can learn to conduct those yourself. Make sure you find people who deliberated before making the purchase, and who made the purchase in the recent months. See How to Select Buyers for Purchase Story Interviews for more tips on that.

Using purchase interviews allows you to understand the forces that acted in the mind of the buyer, what progress they were trying to make, and the interesting jobs for which they hired your product.

I didn’t set out to become a better buyer by choosing to learn about Jobs-to-be-done. That was a side-effect. But at some point I realized that being cheap wasn’t helping me create empathy for buyers. Learning to be a better buyer educated me on the kinds of discerning buyers I wanted to attract and serve.

And buying right has this one extra benefit: I’m making tons of progress.

Stay sharp!


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