Honesty, and Other Ways to Make People Uncomfortable

Bree Weber
Apr 2, 2018 · 6 min read

The problem with honesty is that no one wants it.

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Photo by Austin Chan on Unsplash

I’ve taken to treating my life like one, big experiment. Sometimes, people are really on board with my ideas. Other times… not so much.

Often times, my experiments make people uncomfortable.


It’s easy to talk about wanting honesty and being open to criticism. I decided to put this to the test and see how people truly responded to honesty. Let me start by saying that I wasn’t a dick. I just chose to stop following the social niceties that typically manifest in conversations.

When someone asked how I was, I responded honestly. When someone asked me about my business, I responded honestly. When someone asked for my feedback, I responded honestly.

I noticed a massive uptick in awkward silences, changes in conversations, and filler phrases such as um, uh, etc. Now, this wasn’t the case with close friends and relationships; but with colleagues, strategic partners, and acquaintances, my honesty, especially about things most people consider negative, left them feeling uncomfortable.

I believe it’s because we feel like we need to put our best foot forward when meeting new people, as well as in business settings. As a result, we pretend like everything is amazing 24/7, even when it’s a lie.

Here are some sample conversations:

Catch up call with acquaintance/colleague

Her: Great, this year has been incredible, I can’t believe it’s already March! How about you?

Me: This week has been a bit difficult, I think it’s because I haven’t spent time getting clarity on one of my projects. So, it’s of my own making.

Her: Oh… {awkward silence} well, I’m sure you’ll get it figured out. {changes subject} Anyway, did you get a chance to look over my website?

Me: Yeah, I got your email about it and had a few notes. {gives 3 recommendations}

Her: Oh… everyone has absolutely loved the website. You’re the only one who’s really given me… feedback.

Me: Do you still want me to share my thoughts?

Her: Is there more? Um, I think I’m good with this.

Me: {puts away 10 point list of recommendations}

First meeting with referred connection

Me: Thanks for the offer, but I don’t feel like I need to be served in any way. I was just hoping we could get to know each other.

Her: {awkward silence} I just mean… I’d like to support you in your endeavors, if I can, in any way.

Me: Well, I’m really focused on improving my writing; would you be interested in sharing your thoughts on my articles?

Her: Um, sure. {awkward silence} If you’re looking at growing your passive income, I’d love to tell you about an opportunity that….

Networking event

Me: I pilot business ideas and test out career paths. Every week I need to meet drop-off conditionals in order to continue the pilot idea for another week.

Him: Wow… that sounds really interesting. What happens if you don’t meet your, uh, conditionals?

Me: I consider it a failure, learn as much as I can, and move onto the next pilot idea.

Him: So, it’s just succeed or fail?

Me: Yup, just like in life.

Him: {awkward silence} {excuses himself to talk to someone else}


In the entrepreneur and startup world, we talk about failure a lot. It’s a badge of honor to share your past failures and lessons learned with your peers. It’s like we’ve all been initiated into entrepreneurship with a deep dive on the pure glory of failure, because without it, we’re taught that we’ll never achieve success.

But there are limitations to this failure talk. If you follow the status quo, your failure will be seen as heroic and necessary, but if you go off-script, you just might be seen as a failure yourself.

The script goes like this:

I/We started [insert company/idea here] to solve [problem the idea solves] by [solution hypothesis]. After [timeline of 1–18 months] I/we learned that [mistake in approach], but this fast failure was indispensable to [recent achievement or milestone] because it helped me/us [new project approach]. Even though failing was [negative feeling] at the time, I/we would 100% do it again because it led me/us to [how idea’s new approach solved original problem].

You’ll notice some clear markers here that are essential to script.

For starters, the starting problem and idea to solve it remain the same. If anything changes, it can only be your team’s approach to solving that problem, and typically not the solution (or – heaven forbid! – the original problem) itself.

Secondly, including a timeline of more than 4 weeks ensures listeners that you didn’t rush into anything haphazardly. Keeping the timeline below 1.5 years proves that you did the hard work of really, truly testing that original approach. You were dedicated, damnit!

Finally, you should really stress how important that failure was. Focus on what you couldn’t accomplish without it, and how that failure was super core to your success now. This helps reinstate that failure must always serve a purpose, and you have purpose.

I abandoned the script altogether.

I talked about my failures openly, even the ones that I hadn’t learned from yet. Even the ones that didn’t serve a purpose. I got one of these three responses:

  • Well, don’t be so hard on yourself. Try again!
  • You clearly didn’t give yourself enough time. Don’t give up!
  • We learn from failure not success. Everything happens for a reason!

Reassuring statement followed by encouraging statement, even they’re following a script!

Doing Things Differently

When I launched Pig Pilots, I decided to be very transparent about what I’m doing and why. This means anyone who cares to follow along can see my strategy, track my progress, and knows whether I succeed or fail.

I anticipated that when I succeeded, I’d receive praise, and when I failed, I’d received feedback on mistakes that I’d made and suggestions for next time.

Instead, I made people very uncomfortable.

Whether I was failing or succeeding, I received the exact same feedback – that there was a better way to do things: the way everyone does it.

I was downright startled by this undiscerning response. If I’m getting great results doing something unique, why should I do what everyone else is doing?

So I dug a little deeper, and I asked for more information. Here are some actual responses I received:

To be honest, [what you’re doing] makes me feel really anxious.

I just think people will get the wrong idea unless you [do what others are doing].

If you really loved it, you’d [do what everyone else is doing].

These responses have me speculating that it’s not about me at all.

Once one person or a group of people find success, we all look at that path that resulted in success as the be-all, end-all. We look at that path as the done thing, the way to get success, and the way to show that you’re truly passionate about your goal. In other words, we create another script.

We create a lot of scripts in our lives: to talk to new people, to share our vulnerabilities, to do something new or different. Going off-script will always make people around you uncomfortable, because there isn’t an auto-pilot response anymore.

But going off-script has helped me do some pretty awesome things, like rediscover who my friends vs acquaintances are, and approach my life in more fun and challenging ways. It’s helped me to improve as a person and be more successful in my life.

I’ve cut out some of the BS and noise, and even though it made some people uncomfortable, it made me all the happier.

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