Put yourself in uncomfortable situations

One of the biggest changes in the workforce in the new millennium is that we have to be information synthesizers instead of information producers.  All information is available online.  So we can’t add value by memorizing it.  We have to add value by reframing it. I call this synthesizing.

IBM conducted a survey of CEOs to find out what they thought were the most important leadership skills of the near future. And in the top five was boundary spanning, which is networking ideas and collaborating in order to synthesize information in new ways.

Side note:  I have a theory that this is why we suddenly are noticing how many people have Asperger’s, because it used to be that people with Asperger’s were extremely valuable for their memorizing capacity.  Today, when we don’t need to hire people to memorize things, people with Asperger’s are suddenly viewed as weird and unemployable instead of savants and extremely valuable.

This made me start thinking about how we create that unexpected clash of information that leads to new ideas.

Organizations have been spanning boundaries for decades as a way to expand their brand equity. For example, Shell Oil sponsors the Van Gogh Museum in Amsterdam.  Shell has a prominent facility in Amsterdam.  Shell funded research into how van Gogh chose paint, and as part of that, Shell offered up their research facilities and their own researchers to do lab work on the project.

As the collaboration got deeper and deeper, the result was a ten‑year investigation of how van Gogh taught himself to paint through color, and how we can understand color in different ways today. One of the most memorable results is that van Gogh experimented with destabilizing red pigments, which means that today many of his paintings have become more blue than they originally were – like the walls in The Bedroom.

This changes our understanding of the bridge between the impressionists that van Gogh hung out with and the colorists, such as Matisse, that van Gogh provided a bridge to.

But how can we as individuals span boundaries in order to become better at information synthesis? Pair yourself with unlikely people.

1. Go somewhere you don’t fit.
Travelers to other cultures are the obvious example of people spanning boundaries. In the past I talked about how stupid travel is because people generally use it as a method of getting away from the problems in their life. However, you can use travel as a way to address the problems in your life if you use travel to do a specific job.  If you set out to solve a problem and then you need a different type of information to solve that problem, you can travel to create that solution.

This is very different from traveling to get away from your problems, because when you travel to get away from your problems, you don’t have a very specific solution that you’re on a mission to discover. A test of whether you’re using travel productively is whether or not you have a very clear way to implement the results of your travel once you get home.

2.  Work with people you don’t like.
When you get hired, your job is not to do your job description.  Your job is to help your boss. The boss that you’re most likely to give the most help to is someone who doesn’t share your skill set at all.

This means that if you’re good with people, you need to work with someone who is terrible with people.  If you’re good with numbers, you should work with someone who is terrible with numbers.

One of my most successful attempts at being an employee was when I worked for a CEO who was a frat boy. He was still wearing his fraternity sweatshirts ten years out of college.  The chief marketing officer was his fraternity brother, and so was the CFO.

When we sat in meetings, my sole purpose was to be the intellect in the company.  They never would have hung out with me outside of work because to them I was boring and overly concerned with the future.  But they needed me a lot because my way of thinking was so different from theirs.  Most of the great ideas we came up with were a combination of my ability to see the big picture and their ability to make my ideas fun and saleable. 

3. Make yourself nervous.
I made a rule for myself that I can never hire people that I coach, but it happens all the time that I coach someone and fall in love with the idea of working with them.  I coach such smart, interesting people, and they’re usually backed into a corner because they’re very good at something, but the thing they’re very good at is not working at that moment.  So even though I have a rule for never hiring people I coach, I end up hiring them all the time.

When I was dictating posts to Melissa we had a few problems.  I could talk faster than she could type.  She got frustrated when I made corrections and she always wanted to add her two cents.

Melissa is not a focus‑in‑the‑moment person.  Melissa’s brain is wandering all the time to new ideas.  So we can’t have two people wandering to tons of ideas if one person is supposed to be writing down the other person’s ideas.

So I was coaching this woman who is a court reporter, but the court reporter business is going to India and she doesn’t know what to do. Of course, I hired her to write while I dictate blog posts.

She can write so fast that we can actually get five posts done in one hour, but only if I’m focused. So what ends up happening is I get really nervous before our scheduled call, because there’s no reason for me to pause.  I should be dictating posts the whole time which means I have to prepare, and it means I have to commit to posts that I think I’m going to write, but maybe I don’t want to write.

Dictating posts to Carmen also encourages me to take more risks, because the posts go so quickly that if they end up being stupid, it doesn’t matter.

I would never have dreamed of hiring a court reporter, but when you pair yourself with someone you never dreamed of pairing yourself with, you do things that you never dreamed you were able to do.

The point here is that the risk takers will rule the next millennium. This is how we find a clash of new ideas and a surge of creativity, by taking intellectual and emotional risks. The other reason that risk takers will rule is that Generation Y is risk averse because they’re people pleasers and Generation Z is risk averse because they are consensus builders.

The last fifty years have been dominated by Baby Boomers and Gen X—two generations known for taking risks. As they retire, there will be a dearth of risk-takers, yet the need for risk takers will be increasing. So those who can put themselves if very uncomfortable situations, on purpose, will have the most to offer at work.

Posted in Management
42 comments on “Put yourself in uncomfortable situations
  1. Gary says:

    Another skill rising to prominence is argumentiveness. Our Vice President of operations finally realized sycophantism gets the company nowhere. Now, his meeting assignment points all finish with, “debate and communicate”. What used to be “crossing” superiors is encouraged, to generate as many ideas as possible. And yes, this even goes on down to the people on the floor. Accordingly, our productivity and sales are taking off. I don’t know who said it first, but Nick Saban says, “If we always agree on everything, then one of us is unnecessary.”

    • Ijeoma says:

      Debate and communicate! I really like that because it’s important to have an opinion. Nodding along gets old and doesn’t show your analytical or communication skills.

      I continue to make myself nervous and look forward to travel to expand my boundaries.

    • karelys says:

      And so scary!

      Groupthink is scary when you think of so many things that happened in history because of it. Like the spaceship exploding and other tragedies.

      Anyway, I am always scared when my husband 100% agrees with me. It makes me think he just wants to make me happy. And although it’s nice to be validated, I’m happier when someone is covering my blind spot. I know I am smart but no so smart that I can see the full picture from all angles so I need someone to look where I can’t read mentally, emotionally, even physically.

      • mplo says:

        The tragedies that’ve occurred are a great indication as to why groupthink is not necessarily and always a good thing. Groupthink that promotes hatred of and exclusion of people who’re different in some way or other isn’t a good thing, either.

        As a person with a history of developmental disabilities, I’m in constant contact with people who’re different from me, or who I’m different from, due to my persistent refusal to enter into specialized programs for people with developmental disabilities. That also has to do with the fact that Chapter 766 had not yet come into existence when I was growing up, but it more than likely made me stronger, in many ways.

  2. Steven Branson says:


    Great that you wrote this post. Getting lost is sometimes the best way to find yourself. Being in challenging situations either makes you shrink or makes you learn

    Not a big deal, but I went up a path in moonlight after being warned of rattlesnakes to take sunrise photos. No snakes and some of the most amazing sunrise photos…. so challenges are worth it


  3. Tess says:

    Definitely one of your better posts recently – you really hit the nail on the head here.

    My work is building partnerships for a nonprofit organization and I keep seeing more and more articles about how important “boundary spanning” is in moving an organization forward, particularly in a time when no one has “enough money.” Collaborations are key.

    A much needed “kick in the ass” to take more risks in my work and personal life. Thanks, Penelope.

  4. SheilaG says:

    “The boss that you’re most likely to give the most help to is someone who doesn’t share your skill set at all.”

    True, but most bosses also appreciate people like themselves the most, so don’t expect that your great help will be wildly appreciated by the boss.

    • Angie says:

      True—people like to surround themselves with other people who are like them. But a smart boss will appreciate when their staff’s strengths complement their own. The best manager I ever had used to tell me how glad she was that I think in terms of systems, because she just could not. So, she would see a lot of things I didn’t notice, and I would notice things that she didn’t. It really helped when it came to problem solving.

      • karelys says:

        I don’t think all the fault falls on the boss. I think that if you are nice, or make an effort to bridge the emotional gap, then you can show the boss how being different than him/her is not necessarily disastrous it can be good.

        Being different doesn’t mean being on different pages.

        • Wes Peters says:

          It is, of course, critically important to be polite while disagreeing with someone, or when agreeing with them. That aside, there are many people, bosses included, who are never comfortable with others questioning their judgement. My current boss is in his first ever leadership position, and is learning, but is so uncomfortable both up and down the corporate ladder that we sometimes spend more time taking care of him than we do accomplishing actual work. Needless to say, this is pretty counter-productive.

        • mplo says:

          Sometimes, it’s just plain bad chemistry between a boss and a subordinate, and that’s just that. I worked a job for sixteen years in the Customer Service Department of a small local publishing company, and most of my years were good ones. The last few years I was there, however, a new supervisor was brought in to reflect certain changes in the company overall, she became overzealous (like VERY overzealous!), in implementing the so-called new rules, and, since our department had gone from 20 people to six people, including myself, due to attrition (a hiring freeze–when permanent workers left, they simply didn’t hire more permanent workers), three out of the six people left, including myself, ended up filing grievances against our new supervisor. As it turned out, my job was being eliminated, but there was absolutely no excuse for the overzealous behavior on the part of the new supervisor.

          Another woman in my department, who was bi-racial, did an MCAD case, which got denied, and another woman, who was white, like myself, had ADD and a seizure problem, also filed a grievance, also ended up leaving.

          So, our department eventually got outsourced, but there was just no excuse for the way in which this new supervisor behaved, even though she, too, was eventually swept out.

  5. Dale says:

    Hi Penelope,

    I loved your bit about using travel to solve specific problems. I think most people have expectations that travel will automatically change their life, and this is propagated by the travel blogging world.

    I wrote a blog post on the subject:

    Will Travel Make You Happy? Probably Not:

    I believe travel can be useful, but you have to use the opportunity deliberately and more in line with developing mastery in one area or another.

    Anyway, great post!


  6. Candice says:

    This kind of set up is great for a marriage, too.

    • Penelope Trunk says:

      I agree! I my husband is almost my polar opposite — efficient, focused, lives in the moment, kinesthetic learner. His mind never wanders. And I learn so much from being with him. Everything about myself I see in a different light because he approaches all tasks so differently than I do… Well, actually, I seldom even approach tasks since they are so short-term and my head is always in planning-for-the-future mode.


  7. karelys says:

    I love how Carmen and you are two puzzle pieces that fit.

  8. GenerationXpert says:

    Love this:

    “Your job is to help your boss. The boss that you’re most likely to give the most help to is someone who doesn’t share your skill set at all.”

    This is why I got along so great with my boss – and I just hired someone who can do stuff I can’t.

    • Paul says:

      The problem is ego. No human being with any of it is going to be able to communicate consistently with someone whose skill set is entirely different. And bosses need ego more than they need help with their weak points.

  9. Carmen says:

    …and this is why I need another session with Penelope.

    Just seeing my first name on the internet in this post has me paralyzed. In the comments is one thing because I can blend in, but connected to who I am as a person, connected to my own ideas and vision, connected to my job is a different story. I gotta get over that.

    • mbl says:

      I suppose I would have thought that voice to text software would ultimately obviate jobs that rely heavily on typing skills. But surely many other talents, such as stellar listening skills, go into being a great court reporter. How wonderful that you you and PT were able, not just to connect, but to figure this out.

      FTR, the crappy voice to text software that came with her computer is hilarious when my 7 year old tries to use it!

      • Carmen says:

        Voice to text is great for certain things, but you won’t achieve the same kind of flow.

        The one thing humans have that computers do not is comprehension skills. Computers can’t make sense of what you’re trying to say. They just interpret sounds and pick the closest option.

        Penelope doesn’t have to punctuate while she’s dictating or clean up her false starts. She speaks freely. I clean it up and send her a clean draft formatted to her specifications. I research unfamiliar words and names, which voice to text can’t do.

        • mbl says:

          That sounds just lovely!

          After seeing some of the goofy stuff that the v2t program came up with for my daughter, I wondered if there is a site somewhere for people post these gems. Along with the translations, of course, since they aren’t likely to be discernible.

        • Gary says:

          Carmen: The Über Transcriptionist! Y’know, I’ve known court reporters who’ve said typing and reporting were practically oranges and apples (sorry, I HATE overused cliches). Your focusing ability must be phenomenal.

    • Jen Gresham says:

      Hey Carmen,
      I think it’s a really cool idea. Drop me an email. I would be interested in trying out a session with you. I mean, if it works for Penelope… :)

  10. Jo Danehy says:

    I seem to be a master putting myself in uncomfortable situations now mater where I am or what I am doing. Your blog is one of the only blogs I can honestly stay peeled to on MOST posts. I am such a busy person I can only afford to focus my attention on deep thought that might help me understand myself and what I am doing right or wrong. I am like a dog swimming trying to keep my head above water. Your advise helps inspires me to get to land, shake off and try to go on. Thanks

  11. Alexis says:

    I wrote about a similar idea. We need to be in jobs that make us feel uncomfortable if we want any hope of having a successful, stimulating career.


  12. Rachel says:

    This makes me feel better and more positive. I love your blog (even though there are rare moments when I hate it)! I refuse to give it up.

  13. Linda Black says:

    Sometimes you need to travel to get away I think. Clear your head and then think about the issues in your life, maybe in a new perspective. Sometimes something isn’t obvious while it’s happening, but upon reflection you see why it was helpful or how it could be helpful to you.

  14. Aleric says:

    “The other reason that risk takers will rule is that Generation Y is risk averse because they’re people pleasers and Generation Z is risk averse because they are consensus builders.”

    What you actually mean to say is that generations “Y” and “Z” have become feminized. Years of single motherhood and a feminist/PC-dominated education system will do this. Deep down, you know this to be true, as you work to keep your marriage together and vehemently proclaim the virtues of homeschooling.

  15. Stacy Peters says:

    Great post, as usual, but haven’t risk takers always ruled the world? Steven Jobs, Bill Gates, Oprah, etc….key is it has to be an “educated” risk in an area you have real knowledge and value in. Love the reminder for all of us! Thank you!!

  16. Sonia says:

    I always feel comfortable living within my comfort zone both in my personal and professional life. Working with people I don’t like, or going somewhere I don’t fit is always a turn off factor for me. But that really don’t work good for me.

    • mplo says:

      I see your point, Sonia. Working and/or socializing with people that, for whatever reason(s) I either don’t like, or simply can’t connect with has never really worked for me, either.

  17. Melissa Breau says:

    Okay, my comment is a bit off topic but your first line resonated with me about something totally unrelated.

    “One of the biggest changes in the workforce in the new millennium is that we have to be information synthesizers instead of information producers. All information is available online. So we can’t add value by memorizing it. We have to add value by reframing it. I call this synthesizing.”

    I think this is the problem in the publishing industry today. For so long they were producers. Today they are trying to learn to be synthesizers. But in many ways they are failing.

    • Wes Peters says:

      I beg to differ with the generalization “All information is available online.” It would be a sad, sad world if every thought that could ever be thought in human experience had already been thought, and recorded on the internet.

      What you’re responding to is the explosion of information regurgitation, simply because it’s become so cheap to do so and there are generations of people who haven’t yet discovered that they can find the information from the original sources almost as easily as from the regurgitators. In a decade or two, once the mass of people who are still discovering “the internet” has mostly passed away, most of this suck on the internet economy will die away with them, and we’ll have reached the point Tim Berners-Lee envisioned: a world wide archive and point of publication for human knowledge.

      The point the publishing industry has to grow into is not just to get over the idea of repackaging existing ideas onto dead trees attractively, but of how they are going to contribute to being the repository of human knowledge.

      This applies equally to newspapers, which are already struggling and failing to come to grips with “new media.” They had barely started to acknowledge the idea that radio and television were their competitors when the internet happened. Now all but a few papers are figuratively staring around them asking “who stole my cheese?”

    • Penelope Trunk says:

      I think you’re right, Melissa. I think a lot of people go into journalism to report on what other people think. But the jobs in journalism today are for people who will go out on a limb and give their opinion from a fresh angle. Which leaves them much more vulnerable and exposed than an old-school journalist.


  18. Steve Hayes says:

    Really nice post! I read a lot about working out-side of the comfort zone. I know how important that is. Actually, for me this is one of the keys of personal growth. It is a little difficult to apply it because our mind tends to keep us into the comfort zone but we have to do an extra effort to push ourselves away from that. When that happens we can achieve greater success! I know that is true.
    Great sharing!

  19. Gary says:

    My mind is never satisfied. After the initial infatuation with a new job, skill, ANYTHING, I get bored with it. This has been my Achilles Heel my whole life; I require almost constant stimulation. Therefore, I am built to lose, and forget a decent retirement; you know a rolling stone gathers no “moss”. So now I’m about to retrain for the umpteenth time, wish me luck!

  20. John Lee says:

    I think you are confusing the skill with the person. You don’t have to particularity like your co workers, but if they can do that job your workplace is more comfortable. If you are an accountant, why would you possibly want to work with someone that can’t do math, it just makes your job harder.

  21. Lydia Powell says:

    I have really worked to seek out clients with different skill sets as mine. The #1 reason I wanted to begin my own bookkeeping/tax/payroll business is to help those people with fantastic ideas and fantastic businesses make the financials work. So many people have this deep emotional fear when it comes to money and finances, and I never want that to stop them from creating their life’s passion.

    It can be challenging to work with someone who is disorganized when that’s my biggest strength, but it is ultimately so satisfying when I can provide a valuable service.

    This whole post is full of great advice. I definitely need to make myself more uncomfortable.

  22. Martin says:

    Great tips! I am going to try go out of my comfort zone, I am too lazy.


  23. Stephen Bailey says:

    Couldn’t agree more Penelope. Although as a member I suppose of the Baby Boomers, I would say that, wouldn’t I…
    I remember volunteering while at college for interview practice – a large company needed guinea-pigs to be grilled by their HR trainees, unpaid. Turned out they were also looking for the sort of people who would volunteer for such an exercise – an invitation for a real job interview followed…

  24. Claudia Gomez says:

    Being uncomfortable makes you grow. Being ‘in the moment’ forces you to be 100% awake, conscious and present. I believe that putting yourself in uncomfortable situations will allow you to conquer new challenges as well as grow your confidence. One way to overcome challenges and make difficult situations manageable, one must increase our pain threshold for discomfort as much as possible.

  25. Josh says:

    I definitely need to start taking more risks and going outside my comfort zone. It is nice to have a career related reason to do these things. Hopefully that will push me to take the steps to get there.

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