The Best and Worst Jobs for “Questioners”

what are the best and worst jobs for questioners

Gretchen Rubin wrote a book about human behavior, and the psychology of human expectations called “The Four Tendencies“. 

The Four Tendencies is about the four different personality types that most people fit into.

The four personality types are:

  • Obligers: Obligers will do what others ask without much prodding. They like the external structure and expectations of others to drive them. They can have issues setting and meeting internal expectations and goals, though.
  • Upholders: Upholders can meet both internal and external expectations. They make great entrepreneurs.
  • Questioners: Questioners can meet internal expectations, but have trouble meeting external expectations unless they are congruent with their internal expectations. Questioners also like having a lot data and they question everything. Questioners can be tiresome because they want to understand things so much so that they can internalize it. The constant search for more data, combined with a need to understand everything can manifest itself in seeking “certainty” or a “guarantee”.1
  • Rebels: Rebels have trouble meeting both internal and external expectations. Basically if you ask a rebel to do something, you’re likely to be disappointed with the outcome. Supposedly rebels make good independent salespeople because they’re constantly challenged with new environments, etc.

She offers a free “Four Tendencies” personality quiz on her website that you can take for free.

I took it and confirmed what I suspected.

I’m a questioner.

What’s The Best and Worst Job For a Questioner?

For most of my life I have worked for myself.

I’ve found this mostly “necessary”… In every position I’ve ever been in, for the most part, I’ve thought about how I could do the work that I was hired to do, but on my own.

I started three different companies and for the most part they’ve been “successful”.

By “successful” I mean I had a great time building the businesses and had happy customers and was able to sell two of the three companies.

The last business was an e-commerce company. I ran it by myself with help from remote workers, independent contractors, virtual workers, etc.

For 7 years I worked for myself and had to motivate myself to do everything.

Then about two years ago I transitioned into an opportunity as a remote independent insurance broker.

I was still working alone, but now I was working for a company.

The rationale was that insurance is needed and it’s a business that I could build up that has a potential residual income stream in the form of future renewals.

That was the logic anyway.

I work from a home office and don’t see my superiors or have interaction with them much.

Also, if you have never worked in insurance, let me tell you…

It is horrible.

As a new person coming in from the outside for the first time… Insurance is idiotic and antiquated. The rules are ridiculous and governed differently, state by state. The amount of forms and paperwork needed in order to quote, accept and bind coverage is voluminous. Most insurance brokerages, wholesalers and carriers are poorly run.

I have been building a “book” of property and casualty business from scratch.

In insurance, it can take a year or two to start to get traction, especially in commercial P&C, which is what I do.

Insurance is 100% about sales.

You need to make 1,000 calls in order to meet with maybe 50-75 clients. Of those, you may get 10 or 15.

It’s a grind.

What you earn in commissions is split between the carrier, your brokerage and you, and maybe another broker.

But because the customer only deals with you, for the most part, they think they’re paying you the whole premium.

It’s an easy misconception… But they don’t realize you’re really working for peanuts, at least at first.

So, suffice it to say that it takes awhile to establish yourself.

It can happen… It just sucks and it takes time.

Doing it alone adds to the suck.

In the process of selling, I often find myself stuck in analysis paralysis about which clients to approach and how I should approach them.

I debate with myself about the outcomes of the calls before I make them.

The first call is always the worst. Once that’s over, I’m good to go to make more calls… But the first call is seriously painful.

As a “solopreneur” being a questioner can be OK. But being a questioner as a remote employee kind of sucks.

I wouldn’t recommend a solo sales position working for an employer if you’re a “questioner”. But if you’re alone working for yourself, it’s a bit of an improvement.


  1. Seth Godin recently posted about questioning things and creativity. It reminded me of my personality which is to seek more data as a way to provide myself with certainty before moving forward. However, this tendency also can stifle my productivity. When I stifle my own productivity I beat myself up, or get depressed because I’m not being productive. This is a bit of a circular issue as you can probably suspect.