How to take intelligent risks

Recently, I covered my hallway in wallpaper I bought online (via Wallpaper Weekly). Everyone I showed the wallpaper to said the it would be too busy a pattern. But I loved it. So I bought it anyway.

There are a lot of problems with my hallway now — most notably, I used Elmer’s glue instead of wallpaper paste and I’m going to have to pull down the wallpaper and start over. But every time I walk through my hall, I think about how important it is to take risks with my house — because that’s what makes it mine. Which, of course, is very similar to a life. You can live someone eles’s tried-and-true template for a life, or you can make your life your own.

So many of the questions we grapple with in our life are about this very type of risk taking. We know what we want to try, and we’re not sure if we should try it. Moving across country. Writing a novel. Starting a business. Painting a room.

I’m starting to think, though, that we should evaluate risk in terms of process. Do we like what we are doing during the time we’re taking the risk? Because if you enjoy the process, the weight of the outcome is not so heavy.

I liked the solitary process of wallpapering. I liked making copies of family photos and gluing them to the wall. I like seeing how it all turns out — what works in my house and what doesn’t.

So I ask myself, what is the cost if the risk does not work out? But when I consider process as well as outcome, then the scales often seem to tip in favor of the risk. Here’s are five things I keep in mind when assessing risk:

1. Long-term regrets are usually about not taking more risks.
If you ask people at the end of their lives what their biggest regret is, it’s common for the regret to center around not taking more risks. The same is true of younger people. Ran Kivets is a psychologist at Columbia University who studies winter break. He says that in the short-term college kids regret not having studied enough, but in the long-term, college kids regret not having had more fun. So it’s no surprise that of the most popular posts on my blog is about regrets over getting straight A’s. (Hat tip: Joshua Althouse Cohen)

2. Being wrong costs very little.
In general, people don’t care if you’re wrong; it’s your life and you get to make mistakes. Also, in general, people don’t care if you’re right because they are too interested in themselves. And okay, it’s true that if you invest a lot of money being wrong costs a lot, butut there are very few risks we consider that require a huge outlay of money and a 100% risk on that money. Instead, risk-taking generally requires a relatively small percentage of the money you can earn. Fortunately, the way we get the most happiness from spending money is by spending on experiences. And what better experience than taking a risk and finding out what it will be like.

3. People bounce back faster than they expect.
Most of us are much more resilient than we realize. Daniel Gilbert, professor of psychology at Harvard, explains that we each have a set-point for how happy we are going to be, and we mostly just stick there. Winning a lot of money doesn’t make us much happier, and losing the ability to walk doesn’t make us much sadder. So it’s fair to conclude that most of us overestimate the impact risk-taking will have on our lives.

4. Don’t make the risk bigger than it needs to be.
For example a lot of people think they need to quit their job to try starting a new company (you don’t) or someone who thinks they need to completely dump one career to try a new career (you don’t.) The best risk takers are in fields like entrepreneurship, hedge fund management, and excavation. The thing these people all have in common — those who are successful in their field — is that they are constantly working to mitigate risk before they take the risk. Sometimes just looking at how someone else has approached your challenge can show you a less risky approach to taking the risk.

5. Most risks turn out fine.
In our minds, that is. Gilbert shows that we are able to reframe a poor decision in order to think it was a good decision. Having kids is his favorite example to use. Having kids makes us less happy, but we invest so much time and money into raising kids, that we’re able to convince ourselves it made us happy, and we don’t have regrets. And successful people who make big career mistakes are able to reframe the mistakes so they don’t matter. Also, inherently positive thinkers don’t usually have regrets over the long-term. (Wondering if you are one of these people? Take the test (middle of the page)

You might have noticed in the wall paper picture that there are a lot of lumps. That’s because I was so excited to get started the day the wallpaper arrived but it was 9pm and I didn’t have any wallpaper paste. So I googled and it looked like I could use Elmer’s glue. So I did. Five bottles. And it would have worked, but I didn’t know you put the glue on the paper and not the wall. So I have to tear down the paper and start over. But I don’t care. I like the paper and I had fun learning how to do it.

Posted in Entrepreneurship, Finding a career, Quitting, Self-management
61 comments on “How to take intelligent risks
  1. Jeffrey Deutsch says:

    Hi Penelope,

    Interesting points about taking risks! Goes to show that whichever way we go sometimes, we wonder about the road not taken.

    Also, it takes a mature adult like you to admit she made a mistake, even on something as mundane as setting up wallpaper. Keep up the good work, Penelope!

    Jeff Deutsch

  2. beans says:

    I recently have experienced risk taking that turned out really well. I applied for a job that I really wasn’t sure I wanted. I negotiated and asked for twice the pay they were asking. I got the job and really love it! No regrets!
    The risk turned out fine. You are so “spot on” with this post!
    Love the picture, by the way.

  3. jim says:

    Using Elmer’s glue because a Web search said it was possible, but then mucking it up, sounds just like something I’d do. But I end up with the opposite reaction, which is being pissed at myself for making a frigging mess out of my wall and having to double or triple the work to undo it and do it over.

    Funny how I’m much more of a risk taker at work, where too many failed risks, or one that fails spectacularly or in the wrong way, can get me canned. But I have a sense of adventure at work that I lack at home.

    I’ll bet I could put a therapist’s kid through college working out that one.

  4. claudia bullmore says:

    Thanks Penelope for your keen insights and unique voice. I really enjoy reading your blog. I recently took a risk and went on a 3-week road trip to research community habitats, i.e., cohousing, in 3 states and wrote about my adventure on the blog: twochicksandaguppy.wordpress.com. It was an adventure beyond my wildest imagination. I am not the same person because I took a risk__ I feel expanded. This world needs pioneers and risk takers more than ever. Thanks for the inspiration!

  5. Chris says:

    Thanks for this post. Risk-taking is not something I engage in often, but it helps to view it as an experience and not just an end-result.

  6. Jenny says:

    I’ve recently been thinking about thinking versus doing. I do a lot of thinking. I don’t know that I do a lot. Mostly because I’m scared or unsure. I’m risk averse. I appreciate this reminder that you can think, and do, just as long as you’re not immobilized by fear.

  7. Amanda says:

    Thanks for this post. I recently saw Erick Goss speak at a conference on media trends, and the best advice he gave was to find cheap ways to fail because there were no guaranteed solutions. It’s always when successful entrepreneurs give a reminder to those of us who are a little more “risk-averse”

    • Penelope Trunk says:

      Finding cheap ways to fail is such incredibly great advice. Sometimes I think that finding expensive ways to fail is just a cop-out –it’s great justification for not doing anything at all.

      -Penelope

  8. Erin says:

    I love that wallpaper.

    If I were you, I’d use black and white photos inside the frames rather than color. I think the color makes it busy…but black and white (or something else mono-chromatic) would make it really fantastic. That’s my non-expert opinion.

    • Penelope Trunk says:

      Yeah. Agree. I love that I can get interior decorating advice on my blog!

      Penelope

    • Laura says:

      I like the black and white idea too. I have always been partial to sepia toned pictures…there is somehting about the lighter and darker tones in a sepia picture that makes it really pretty (to me, anyway)

  9. Robert says:

    I truly am a devotee. I like the content of your post. But didn’t you mean to say “our” house instead of “my” house? I mean my wife will often use the word “my house” and I feel like her use of words reflects a deeper set of thoughts that our house is seen as “her” house by her. Sorry…I know this comment is tangential to the blog post..

    • Kristin says:

      Funny, that was the first thing I noticed about this post. It immediately jumped out at me and I thought “I would be very upset if my husband referred to our house as “my” house”.

      • Penelope Trunk says:

        Yeah. This is a problem. I noticed it when I was writing it. I decided to leave it though, because it is, really, how I feel. I know it’s messed up. I know I should feel more “we” about it.

        The farmer has lived in this house alone for twenty years, though. And if he dies, the kids and I will likely be thrown out of the house immediately. So it’s really always going to be his house.

        I don’t even know why I’m writing this. I guess because I feel like the situation is messed up and my blog is my therapy office. And anyway, it’s fun to have conversations in the comments section…

        Penelope

  10. KateNonymous says:

    “Gilbert shows that we are able to reframe a poor decision in order to think it was a good decision.”

    That’s what my mother called choosing to be happy. If you [generic “you”] decide that you are happier because you have children, who cares what the study says? Thinking you’re happier is really what matters in a lot of cases, because it’s your perception of your life. And I think that’s something that gets lost when studies quantify emotions like happiness.

    By the way, I like that wallpaper. I think it says a lot about you.

  11. bobby says:

    “Because if you enjoy the process, the weight of the outcome is not so heavy.”

    Couldn’t agree more. If someone does something just to say they did it (like running a marathon or climbing the Great Wall of China), but didn’t enjoy the actual experience of having done it or the accomplishment itself, it was probably a waste of time.

    • Margaret Goerig says:

      And that, Bobby, reminds me of one of my favorite quotations so far in the book I am reading, Blue Highways, by William Least Heat-Moon: "Any traveler who misses the journey, misses about all he's going to get."

  12. barbi says:

    I wouldn’t call using Elmer’s glue to wallpaper an “intelligent” risk, I mean we all know that Elmer’s glue is frustrating on even the most simple homework projects with the kids…. In fact I believe Elmer’s glue and intelligence do not ever belong in the same sentence, I’d even go as far as to suggest that Elmer’s glue should be banned because of the misrepresentation that it actually sticks in a glue-like manner. I think vanilla pudding does a better job at sticking, or spilled Sprite. Besides don’t they use donkey hooves for making Elmer’s glue? Like wasn’t Elmer that farmer who invented turning his old donkey’s feet (the one that bucked his wife off, caused a concussion which lead to all sorts of sticky trouble with the law) into
    Elmer the Donkey glue in 1932?

    • Jim C. says:

      No. Elmer’s Glue-All was made by the chemical arm of Borden (now Borden Chemical Company). Borden’s well-known advertising cartoon characters were Elsie the Cow and Elmer the Bull. It had nothing to do with a donkey, and it’s not made from hooves. It is a polyvinyl acetate product designed more with safety in mind than for bonding strength (i.e., it’s safe for elementary school kids).

      • barbi says:

        Oh dear Jim you caught me out, but I Wilkipeed same as you did and then took some liberties with the tale of Elmer’s cow and bull story, matching them to Penelope’s hilarious tales of the naughty donkey at her farm, my humor seems sadly lost on you but was rewarded with a factual comment indeed…

  13. Just Sayin says:

    Like the post about risks, and think evaluation of the process instead of potential outcomes is brilliant.

    Concerning the wallpaper: It would look better above a chair rail instead of all the way to the floor.

  14. Van says:

    Ah, this post warms my heart and inspires me to take more risks. I’m working a “dream job” as a writer because of risks. Two years ago when I was 21 I quit my job, moved back in with my parents and lived on savings and applied for writing work all day and night, submitting hundreds of resumes daily until I found my dream job seven(!!) months later.

    It was a risk, my parents and friends thought I was insane but it paid off. And now I’m taking more risks working countless hours starting up a couple of side businesses. No money yet on the new ones yet, but I’ll keep working and eventually THERE WILL BE.

    ALSO on your sexy new wallpaper:

    – you can add prints of art that inspires you
    – make the kids feel proud by posting their latest artwork within the frames
    – write in inspirational quotes to stay motivated
    – risk adding some drawings of your own, lightly, in pencil or something else that can be changed on a whim

  15. Sonia W says:

    I noticed when I was Dispatcher years ago, a ex-coworker had been in the same position for 12yrs making peanuts in my eyes. For her being in that position was her comfort zone. She never wanted or expressed a need to leave or venture out to see what else was out there for her. I remember feeling, what would anyone stay so long in one position and never want to learn anything else?

    I eventually left after 5 yrs and started with a start up company during the dot.com boom. Then left to do a stint at Yahoo and Google years later.

    To me those were the best years of my life working and has given me the experience and drive to learn more. The valuable lesson I learned was: “The more you know the more valuable you are”. If it’s within reason, take a chance and go for it!

  16. Tanya Lacours says:

    Penelope- I have been reading your blog for years and it is so great to see your recent increase in posts! I truly look forward to them.

    Your post today is a really great reminder for me since I feel like giving up everything I have built over the past couple of years and starting completely from scratch in a new place. But I know myself, and I am not particularly keen on the process of starting new. I’ve done it several times.

    Instead, I will look closer at what smaller risks I can take. And it’s refreshing to read that having children does not make you happier. I have never wanted to have them and now that I am 32 a lot of people ask me. Like even the car salesman.

  17. Matthew says:

    Your wall reminds me of the wall at the US Holocaust museum

  18. Harriet May says:

    I love the wallpaper. I love taking decorating risks, and our latest was to paint our bathroom green. Oh my gosh, it’s so bright. But now I like it, so it was worth it. It’s kind of like being inside a giant margarita, and when could that ever be bad!

    It’s also a risk because we live in an apartment and who knows if we’re allowed to paint the walls. But I live there now, and I can’t live inside a beige box. Maybe that color was designed for the non-risk takers, but if I have to paint it back to beige I might die in the process. So I think I’m going to start a fund so we can afford to pay someone to paint it back when we move out (mitigating risk). Also, the whole process of decorating our apartment brought me and my boyfriend closer together, and we learned that we actually have similar tastes in interior design. Who knew! And he’s a risk taker too: it was his idea to buy a bright red sofa for our gray-and-turquoise-painted-great-room. It looks fabulous.

  19. Matthew says:

    Here is what the wall looks like.

  20. Annie B says:

    And now I’m ordering wallpaper samples – something I had no plans to do until I read your post – okay, that’s not the point of your post, but – thank you! And. . . it is great to see risks put into perspective. Usually, people divide the world into ‘risk takers’ and those that don’t. As if there were some genetically coded ‘risk’ factor, and either you have it, or not. But, what a better world where “Have you taken a risk today?” might become a new greeting, rather than “How are you?” or “W’as happening?”

  21. barbi says:

    Glue jokes aside, just peel pieces off, leave others, take real creative risks, look at Peter Beard, Karen Blixen (a farm in Africa inspires a farm in Wisconsin?) to create a collage that is uniquely yours, cause that wall paper is a bit uptight. A fabulous source of inspiration always is J Morgan Puett, designer, farmer, artist in PA:

    http://www.jmorganpuett.com/index1.html

    • Penelope Trunk says:

      Great link. Thanks, Barbi.

      Something I have been noticing is that when I take more risks in posts — sort of veer off to the edge a bit in what I talk about — then commenters do the same. And the learning curve (for me, at least :) goes up exponentially.

      Penelope

  22. Kathy says:

    Penelope…Thank you for your comments today. I think that I take a risk running my shop and not having a paycheck every week (in fact, not most weeks) but I love what I do so much that I hope in the end it will be worth it to have taken the financial risk. My husband is not so sure. My point is, I think that if you are happy doing what you do & you can keep your head above water financially, isn’t it worth it to do what you love instead of worrying about the money?

  23. Tina Portis says:

    Gosh, I’ve been in my own place for over a decade. Built my own home in 2008 and have never painted or used wall paper on my walls. After reading this, I realized that I take intelligent risks on everything and everyone except “me” where it really matters. So, I found this site http://www.wallwords.com where I can put power words on the wall. So, here’s my project for 2011! Thanks Penelope!

  24. Kathy says:

    P.S. I’ve seen Penelope’s wallpaper & it looks NOTHING like the wall in the Holecaust Musuem. I LOVED it!!!!!

  25. Kat says:

    Love the wallpaper. Good pick!

  26. Jennifer says:

    You said it! I always feel it’s ridiculous when people insist you have to quit your job before starting your business. Granted, you may have to adjust the timeline, but that’s not necessarily a bad thing. And that bit about “are you enjoying the process” is so essential – whenever something in my life hits a road block (business or personal), I always remind myself, I’m doing exactly what I want to be doing, so no worries. (Now to go read those links!)

    Jennifer

  27. Mark W. says:

    Very good post regarding risk from mainly a solitary perspective.
    However, I think the first thing that needs to be established regarding any risk is whether it’s a solo venture or involves other people. If it involves other people as it often does, communication and negotiation in the beginning and on an ongoing basis become key factors. Successful communication and negotiation between people in a joint venture helps the process and the outcome become more enjoyable.
    You’re very open about your life here on this blog so I’m going to comment on the following sentences as you did above in the comment section –
    “But every time I walk through my hall, I think about how important it is to take risks with my house – €“ because that's what makes it mine. Which, of course, is very similar to a life. You can live someone else's tried-and-true template for a life, or you can make your life your own.”
    While it’s true it’s your house, it’s also the farmer’s house and your kid’s house because they live there too. I’m hoping that you have some sort of agreement/understanding with the farmer and the kids regarding the interior decorating of the house. I have to wonder though how much input and consensus there is going on when I read from a previous post – “What we ended up with are colors that make me happy and creative. In fact, these are the same colors I chose for my childhood bedroom.” I’m guessing there’s some communication and negotiation going on here based on the “What we ended up with …” part of the sentence but you did get your way nonetheless. There’s also something else that happens when you get your way here. You transfer the joint risk to a solitary one and consequently the rewards/benefits from a journey (and sometimes outcome) perspective are solitary. Some risks (and associated journeys and outcomes) are joint but you’ll want to do them yourself anyways – that’s a risk in itself and okay as long as you’re aware of it and know yourself. This is the thing though – it’s easier to ask for help and can be more fun (or not) if the joint risk is done with someone else. And then there’s some risks that are joint that just need to be done on a solitary basis (at least to some extent). It’s complicated and details for each joint risk on a case by case basis need to be addressed but communication, negotiation, and maybe even compromise are important.

  28. Tom Hawkin says:

    Great post! I’m always trying to encourage others to not be so scared of risk. When you really stop and take a look at the ‘worst case scenario’, it usually ends up not looking that bad. If you want to make a major change for the better in your life-you’re going to have to take some risk at some point. They key (as Penelope noted) is to take calculated and smart risks.

    tomhawkin.com/career-blog

  29. Josephine Hanan says:

    You used 5 bottles of Elmer’s glue? That’s hysterical and I love your determination to just go with it and abandon trying to “get it right” or do what other people you “should” do …although they don’t even live there!

    I was intrigued by Daniel Gilbert, professor of psychology at Harvard, explaination that we each have a set-point for how happy we are going to be, and we mostly just stick there. The question in my mind then becomes, how can we raise the set-point, or can we?

    Overall, my biggest takeaway from your post was that stepping out of my comfort zone to take a risk doesn’t mean I have to be uncomfortable with the risk I’m taking, because more often than not..it’s a risk in which the cost of not taking the risk outweighs the downsides of taking it.

  30. Christopher Flett says:

    Great article. It seems in my experience that most people don’t achieve their goals in business because they are afraid to go ‘all in’. They want to keep one foot in something else ‘just in case’ which sets in their mind that if they fail, they have a back up plan. The most dangerous person in business (in a positive way) is someone who has nothing to lose because they commit 100%.

  31. Yuan says:

    The title of your post is “how to take intelligent risks,” but the rest of your post is just urging people to take risks of all kinds. I agree that taking risks is important (and fun!), but some risks are just plain stupid and harmful

    So maybe your next post should talk about how to avoid taking stupid risks?

  32. Patrick Garmoe says:

    Hi Penelope,
    Enjoyed the post, and couldn’t agree more. Too many people are so risk-averse that they remain in jobs they hate for years or even decades, instead of looking around for other options. I was laid off a year ago, and it has made me mentally richer than I could have ever imagined. Whether it’s a job or something else, the risk these days is in not taking a chance. Because what passes for “security” these days is largely a mirage anyhow.

  33. Casual Surfer says:

    Timely post, I’m taking a small risk right now. I’ve decided that if the “rules” require me (a woman) to wear a men’s shirt in order to represent my employer at a tradeshow, I’m breaking them. No one would expect a man to cross dress & wear a blouse (with darts or additional seaming) so why expect a woman to wear a man’s button down shirt?

    It’s a better outcome for the company as well. I’m more comfortable and more confident when I’m wearing clothes that FIT and I feel good in. That’s the right frame of mind to be in when talking with dozens (or hundreds) of people. I might be the first person to take such a stand at this place, but so be it.

    • Techquestioner says:

      Good for you. Even the military doesn’t have unisex uniforms! Lots of clothing companies that sell company- branded business attire (polo and dress shirts, for instance) offer feminine versions of the same shirts. Tell your HR department to ask whoever orders the company shirts to order appropriate ones for you and the other ladies.

  34. Steph Bruno says:

    Penelope,

    Your post reminded me of a quote from Lucille Ball:

    “I’d rather regret the things I’ve done than regret the things I haven’t done.”

  35. Cindy Allen says:

    Is the farmer charmed by all of this experimenting on “your” house that you would be thrown out of immediately upon his death? It makes me sad just typing that. How’s it all going? I know you were head over heals for the guy, but it’s got to be kind of nuts for him since you all moved in. Are you supporting each other? I’m just curious. Just tell me it’s none of my business, because it really isn’t.

    As someone who was married for 25 years then divorced, the topic of entering into another long term relationship is interesting to me. Why, what is the plus side of it, etc….I’m very happy single (six years now) and have had wonderful male relationships. Just not eager to enter anything lifelong for some of the reasons I’m seeing here…You sleeping on the porch to avoid the farmer because of your home decorating choices being one of them.

  36. Cougel says:

    Great post. “do we like what we’re doing during the time we are taking the risk” is everything!! Posted this to my facebook.

  37. le@thirdontheright says:

    love the paper by the way … le

  38. Jing827 says:

    I love to take risks & try on new ideas. It’s the only way I think we can learn through life, instead of “playing safe” all the time.

  39. Nadine says:

    Yes! Yes! Thank you for the article on taking risks. I couldn’t agree more. Thank you for reminding me that weighing in on the process, thsat enjoying the process changes the whole equation. I have taken large risks in my life because I did not want to have the regret of “I didn’t try it”. Risks Don’t always pay off in ways I expect, but the experience alone and lessons learned are usually worth it.

  40. Paul Hassing says:

    What a great post! We’ve been talking about risk on a couple of our blogs and Joanna Maxwell just flagged yours. It was well worth the trip. Many thanks, Penelope! Best regards, P. :)

  41. Ryan says:

    First off who are they to say that its too busy or whatever. I like it but really even if I didn’t, its your life and your wall. Also some risks can cost you and not just talking bout money. Some people take risks and are wrong or they fail in that instance but they never learn the lesson from the experience. In that sense it cost them. The quality of our life is based on the valuable lessons we take away from each and every experience.

  42. angie says:

    Love the wallpaper. Let someone else put it up ;)

  43. Sheldon Mohl says:

    I’m not into decorating much, but can relate to taking risks. Go for it! Chances are you’ll feel better when you look back and reflect anyway, so why not?. Be happy & constantly work towards your goal (mine is getting employed) everyday. I have learned from the experience. Thanks for letting me post my 2 bits.

  44. Jerry says:

    The wallpaper seems to have inspired a lot of thought. Gluing empty frames to the wall would have been too strong a statement, for sure.

    When I was a child, we made “paste” by mixing flour with water. I understand that Elmer’s used to do the same.

    I have always found it interesting that people are generally more comfortable with a display than a barrier.

    Don’t let walls get in your way.

  45. NairaBrains says:

    Can’t agree more with your points.

  46. Danielle Webb says:

    Whoah, that is some awesome wall paper. I have also been playing around with my interior decor recently. I personally find wallpaper way too much hassle, especially when it comes time to replace it. I have had some really good results with vinyl wall lettering. I recently ordered some lettering from these guys > http://www.letteringonthecheap.com. I must say I am so far impressed with their product and service. Cheapest place I could find online.

  47. Burt Lovaas says:

    Hi there everyone, I am sure you will be enjoying here by watching such comical video lessons.

  48. Graham Hastings says:

    Whoa, that is some awesome wallpaper! My wife loves it. Probably just a little bit too busy for me though. My wife has been experimenting with wall vinyl recently, placing quotes, and graphics around the place, and I must say it looks pretty cool. If anyone is interested you ought to check out these guys > http://www.letteringonthecheap.com.

  49. hal wulff says:

    Risk taking is for those who want it all. Intelligent choices will yield exactly that if you incorporate it into your mind set. Believe me, I should know. Look at my face book pictures and you’ll see why. (Hal Wulff)

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