Updated on 01.26.09

Making the Hard Choice

Trent Hamm

A few days ago, Seth Godin (my single favorite blogger by far) wrote the following:

Think about how often your goal at a conference or a meeting or in a project is, “don’t screw up!” or “don’t make a fool of yourself and say the wrong thing.” These are very easy goals to achieve, of course. Just do as little as possible. The problem is that they sabotage your real goals, the achievement ones.

That paragraph really hit home for me. There are often times when I’m writing for The Simple Dollar when I have to make a fundamental choice. Do I say something controversial that actually represents what’s on my mind, which risks alienating a portion of my audience but also engages people? Should I reveal something about myself that could be personally painful, especially since almost everyone I know well reads The Simple Dollar? Or do I put that idea aside and chase the safer idea, the one that won’t alienate anyone, but won’t really engage anyone, either?

I felt this same push and pull at my previous job, too. A large portion of my time was spent on software development and system administration. I was in charge of a handful of servers and I was also responsible for writing some code that had to be deployed on those servers. This led to a balancing act whenever I had to write code for a new feature: should I implement the most robust and complicated version of the feature (which would stress the servers more and make my system administration job more stressful), which would wow the users, or should I implement a simple version, keeping people minimally happy and also making my system administration job easier? It was a balance that I constantly had to walk – and it also wore me down over time, because I felt like every choice had become a milquetoast compromise.

One choice is easy. It lets you more or less maintain where you’re at and enables you to avoid having to choose the harder path. The only problem is that, over time, you don’t become known for greatness. You become known for mediocrity.

The other choice is much harder. Whenever you choose to take the hard path, you not only have to take a more active role in things, you also risk alienating people. Yet, this is the only path that leads to great success in life. You won’t be known as mediocre – but you do run the risk of being seen as a failure.

We are given many of these choices every day in our lives. When we go to a work meeting, we can choose to engage the discussion, or we can sit there and be quiet. When we go to church or to any community meeting, we can go out of our way to talk to others, or we can keep to ourselves and go through the motions. When we work on a project, we can do what’s expected and get the job done or we can go the extra mile and develop something truly impressive that also runs the risk of not being widely accepted, either. When the call goes out for volunteers, we can either sit there quietly or we can step up to the plate and give it a try.

One path leads to mediocrity. The other path leads to the possibility of success, but also runs the risk of failure.

If you want great things in your life, the choice is clear. It’s time to step up to the plate and take that risk.

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  1. Your Friendly Neighborhood Computer Guy says:

    I would personally love it if you got a little more controversial on this blog. I’m a big fan of TSD posts where you speak your mind and share your opinion. It may be because I’m on the same wavelength as you on most things, but when our opinions differ, I appreciate how you’re always fair, smart, and concise when you share your opinions, so it doesn’t offend or alienate me in the least.

  2. Nancy says:

    Great post. There are so many folks out there wanting to not offend others or fail at projects. In many groups I am involved with there are the doers and the watch and see what happens types. I like being a doer! When I attend meetings for my job I like to be involved and ask questions while so many others just sit and listen. It is my way of learning all I can.

    I too like the posts that you really share where you stand on something. It brings it all home for me. If it is something I don’t agree with it gives me something to think about. I don’t often miss reading a post so there has yet to be anything offensive to me. There may be things I would do differently but it is in the process that we learn.

  3. IRG says:

    Terrific posting, Trent. As always, your honesty and integrity shine through and really give weight to what you write. So, Bravo for taking the risks to say what a lot others–who worry only about clicks, being liked and making money–won’t say. Cause blogging is really putting one’s self out there and you truly can’t hide (from critics, etc.) so it’s understandable how some may not choose to be as honest/direct/forthright.

    In this topic, you cut right to the heart of the issue with so much of life–and our personal and professional choices.

    Choose: Safe, mediocre. Risky but rewarding. or, of course, risk and failure–and what comes with the “failure”

    It really should not be all that difficult, theoretically, if we are clear on our values. But often the issue is…what is our INTENTION? Something we need to look as carefully at as the results we’d like. (In fact, some might say more important to look at the intention rather than the outcome.)

    This issue of risk, reward…it all goes back to focusing on the outcome and our attachment (both personally and professionally) to the “results.” But the reality is we don’t always influence and/or control the “results.”

    So perhaps we have to go back and focus on our intention. Then if we choose risk, we at least understand and accept where we are coming from.
    And that’s where everything must start.

    Trent writes:
    If you want great things in your life, the choice is clear. It’s time to step up to the plate and take that risk.

    The use of terms like “risk” is, in many ways, a label and an off-putting one. Let’s think about what risk really constitutes: A result we won’t like or will get us in “trouble” with someone, or make us less likeable or popular in others’ minds. Not just lose something for someone.

    But risk is really more about not knowing the outcome of an action versus a “safe” choice, where we THINK we know the outcome or history tells us this is generally the outcome. But think of how many have been surprised when the “safe” choice (as in marriage, work, etc.) turns out NOT to be so safe after all.

    It’s about choosing the known (the alleged “safe”) versus the unknown (the “alleged” risk), but really it’s about whether we choose being authentic or not.

    I’m not judging those who choose NOT to risk. The world can be tough when you don’t go along with conventional thinking, society’s take on things or even your peer group. You do pay a price and sometimes we are just not emotionally (or fiscally!) equipped to make a choice that could harm others as well as ourselves. (Another factor in risk. It’s one thing to risk yourself, entirely another to put others at risk.)

    But to truly live, you have to think about choices not in terms of results or outcomes, but about your goals and intentions. If you’re strong enough to make tough choices, you’ll be strong enough to take responsibility for the outcomes. Regardless.

    Trent, one of the reasons your site shines above others is that you ARE authentic, do take risks by bringing up topics and taking a stand on stuff that some may disagree with.

    But life is about agreeing to disagree.

    Being real and authentic and living a conscious life, with intentional choices, should not be about making a “hard” choice. It should be a lot easier.

    Posts like this shed light and do help make it less risky to BE.

    Thanks, Trent

  4. Joey says:

    There was a time when I was obsessed with standing out, with making a name for myself.

    Fortunately, that time has passed. Simply living is enough for me, and these days, I’m far more interested in doing what interests me than I am in trying to surpass or impress others.

  5. Thanks Trent.

    One of the better blog posts I have read in a while. Very true for a lot of people, including me.

    If I think back to the biggest accomplishments I have had in life, I have followed the harder path.

    It hasn’t always worked, but the alternative wouldn’t be any better.

  6. friendlyfire says:

    Awesome entry & by far one of your best in the short time I’ve subscribed.

    Blogs give the blogger the freedom to be what they are as long as they understand the consequences of putting it out there. This premise also holds for performance in the working world, albeit within the more specific boundaries set by the employer.

    As for typical American business environments – speaking from the wide range of ’em I’ve been involved with in over 35 workin’ years – I do NOT think most arenas reward going the extra mile – at least in the thoughtful, proactive way that I think you mean.

    They are fine w. extra mile as in coming in early, staying late, skipping lunch, putting work before family or personal goals, doing work errands off the clock for hourly workers and continuous “voluntary” overtime for salaried staff, etc.

    My general experience is they want people to do their jobs as defined by the job descriptions (including the freebies described above).They do not want people to ask difficult questions, raise complex points that will take time & money to analyze and resolve if necessary, and above all not outshine their superiors (the concept of mentoring is going under the wave of desperate competition to hold onto jobs). Company-think is very status conscious as that is the way some people in the system define themselves and establish what they think is their superiority.

    Paradoxically for American business, this kills off the very things we need most now – independent thought, analytical honesty, and true vision. These can light the fires of creativity and productivity.

    We used to be a “can do” people. Now we seem more like a tepid “should I?” workforce.

  7. Ranga says:

    Inspiring article.
    I wanted to share a related quote I read recently, “when you always tiptoe, you won’t leave any footprints”.

    Similar to your lines, “The only problem is that, over time, you don’t become known for greatness. You become known for mediocrity.”

  8. Mike says:

    In your professional life the tendency is to play it safe and not make waves.

    Its also a fact that only about 1 in 10 workers have the ability to make things really happen and achieve a result. Thats becasue they’ll take risks for the sake of achievement. Those same folks are also generally rewarded far beyond their peers despite the occasional failure because the ability to achieve results is the best job skill you can have.

  9. chris says:

    Take this how you will, but one of the quotes that changed (literally) the way I look at life was in a real estate investment book by John Reed. It goes like this:
    “Life, to an inescapable extent, is a game of chicken. Chicken is a game where the courageous may win or lose, but the cowardly always lose.”

    Love the blog. In the words of Gary Vaynerchuk, “crush it!”

  10. The Personal Finance Playbook says:

    This post speaks loudly to me, in part because I’m a youngish attorney who still makes a lot of mistakes and fears making them. Good post.

  11. Gayle says:

    Trent, I ALWAYS read your blog, immediately, when it pops up in my email. So odd that we are often on the same wave link, considering my “demographic” is very different from yours!

    I got laid off just before Christmas. Rather than getting out there & trying to replace the job, I decided to launch the business I’d been thinking about for some time. Pretty risky all the way around.

    I’ve always chosen to follow my own lead, maybe not always SPEEDY about it, (didn’t go back to college & finish my degree until I was 40), but if you don’t listen to your inner voice, the one that really wants to TRY IT, you end up very disappointed in yourself. That feels worse than any public perception that you have failed.

    I always think of my Dad. He died suddenly at the age of 46. He had tried all kinds of different things in his life. It wasn’t until he began to do what he had always wanted to do – at the age of 41 – that he was truly content.

    How many of us can say that we have spent five years living in a way that makes us happy?

  12. J.D. says:

    Thanks for posting this, Trent.

    Right now I’m working to put together a presentation for a meeting of the local group of financial planners. My approach has been very much “don’t screw up”. But you know what? That’s probably why my talk is coming off so milquetoast. Screw the people who might think my idea is half-baked. I’m going to change my tone and go in full-bore in support of blogging. I believe it. If they don’t, it’s their loss!

  13. Geoff K says:

    Good post Trent, but I wonder if your overestimating
    the alienating effect of a controversial post. A lot of debate and interest can be stirred up by one, and far from putting many people off your blog it may involve more people. Particularly those with strong views on the subject.

  14. Danielle says:

    I’m all for the more controversial approach. Your writing is so friendly that it really isn’t a burden to be told the honest-to-goodness truth.

  15. DollarDream$ says:

    Hi Trent

    Great post. This is very timely for me, as our company announced the news about layoffs today. They will be reducing the headcount here shortly in next month and now everybody is afraid. During these times, people need to change their attitude from # 1 to # 2 path you described above. I am somwehere in between, but trying to move to the taking risk side.

    I hope this post inspires lot of people and for once everybody stops complaning about how their job suck – because they still have a job! I am surprised even in today’s economy lot of people I know talk about – hating to go to work on Mondays ( the end of weekend fever). What else would you rather be doing?!


  16. This post reminds me of a motivation class I took at my last job. The basis of the class was that all of us are either Victims, Vacationers, or Volunteers. Everyone likes a volunteer. They step up to the plate. They take the risk when everyone else doesn’t want to initiate. We should strive to be the Volunteer.

  17. Michelle says:

    I often face a similar decision on my blog, so I can really relate to this post! I have to admit that when I take a deep breath and go for the post that reflects my true self, the most interesting discussions come from it. But it is more work :>)

  18. Lori says:

    quote for the day:

    Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows neither victory nor defeat. – Theodore Roosevelt

  19. JR Moreau says:

    Really good, thought provoking post. I love thinking about the paths given and the ones we take and why.

  20. Carrie says:

    I worked as a lawyer in a previous life. The lawyer’s motto is “Don’t screw up. EVER.” Needless to say, being a lawyer means avoiding risk as much as possible. That’s why I’m not a lawyer anymore.

  21. Carol says:

    A few years ago our son was the scorekeeper for his older brothers basketball team. He was new at it, made a mistake and was harressed by a couple classmates. He was upset and reluctant to go back. I said to him “where were they sitting?’ meaning the kids who gave him a hard time…I pointed out to him that they were sitting on their butts, while he was doing something. Next time they have a criticism invite them to come on down and work along side you! He got the point…take risks and don’t worry about those sitting on their butts critical of you. When I find that I’m critical of others…I’m sitting right there on my butt not taking any chances! Great post!

  22. Carol says:

    A few years ago our son was the scorekeeper for his older brothers basketball team. He was new at it, made a mistake and was harressed by a couple classmates. He was upset and reluctant to go back. I said to him “where were they sitting?’ meaning the kids who gave him a hard time…I pointed out to him that they were sitting on their butts, while he was doing something. Next time they have a criticism invite them to come on down and work along side you! He got the point…take risks and don’t worry about those sitting on their butts critical of you. When I find that I’m critical of others…I’m sitting right there on my butt not taking any chances! Great post!

  23. richerandslimmer.com says:

    I think you have to find the right balance. Most of the times you should be able to say what is on your mind, but there are situations when that may not be very wise. As long as what you say is not inappropriate for the situation/time/people involved, you should be fine.

  24. Trent, I’ve been a silent lurker on your blog for awhile now, but I just had to comment and tell you how inspired I was by this post.

    Sometimes it’s so easy to take the safe route that we do it automatically and don’t even realize that we’re taking the road to mediocrity.

    Thanks for helping to shake me out of my stupor!

  25. Quatrefoil says:

    I agree with you that it’s better to aim for greatness than mediocrity, but it’s also important to recognise that sometimes it’s necessary to choose your battles. Sometimes I have to go for the easier, less perfect solution because I know that I can get it done in the available time, or with my available energy. It’s frustrating but I’ve learnt over the years that trying to be the best at *everything* sometimes means failing at too much.

  26. Reinder says:

    I agree with the previous poster. Rather than “Playing it safe” vs “Pursuing excellence” being a black and white choice that people make for their whole career and approach to life, most people in the real world, when given a chance, perform a kind of triage. “THIS project is my chance to show how good I am”; “THIS project we’ll do well to get it done as per the client’s instructions”; “THIS project is one we shouldn’t touch/shouldn’t have touched at all” (“shouldn’t have” if you don’t get to choose your project). Wisdom here is recognising the first type when it comes around and taking on as many of those as humanly possible, while avoiding the third type. Bread and butter projects are often the second type.

  27. I agree with you and I can relate. In my job, I was so eager to go to work everyday before. I possess the drive and energy but the work itself is so boring and not challenging. It does not have some self-fulfillment. I asked for some extra challenging work and I did an initiative project but was left unnoticed. Now, my energy and drive to go to work is slowly drying up. I feel I am neglected.

  28. jan says:

    You are talking about risk! Necessary to really be alive is risk. It is life affirming as well. Once I was young, now I am old, life is to be lived to the fullest.

  29. “A person starts to live when he can live outside himself.” – Albert Einstein

  30. Anna says:

    Excellent post, Trent.

    I would like to point out the difference between taking a stand on a controversial subject and revealing personal matters. Both involve risk, but the risks are different.

    When you express your well-thought-out opinion on a controversial matter, some people will complain and others will applaud, and the ensuing discussion will be lively. That’s more than likely to be good.

    When you reveal personal things that might be painful, then you have to balance the potential good to your readers against the possible damage to your psyche. You do need to protect your boundaries. This is a tell-all culture, and that’s not necessarily good for anyone.

    Also, since most people you know read your blog, you have your children to consider. It’s not too far-fetched to foresee that when they are in school, a classmate will come up with “My dad says your dad XXXX” all out of context, but embarrassing to the child nevertheless.

  31. jreed says:

    Isn’t it far riskier to your writing career to bore everyone to death by always covering every basis so neatly that there is no room for discussion? How many people read the “great post” comments? zzzzzzzzzz

  32. Jen says:

    Millionaire Acts, I was recently in a similar situation. Not only was my work unrewarding but it didn’t even fill my time, and there were no other opportunities for me at the company. I finally had a momentary flash of either brilliance or insanity and flat-out quit, with nothing else lined up, in the middle of a recession. I’m not necessarily advocating this path, but for me, that was the hard choice. The very, very hard but necessary choice.

    (Side note: fret not, fellow readers. I had the foresight to prepare a good cash cushion for the day I finally snapped.)

  33. Tom says:

    Well said.
    I think people choose the easy road because it’s comfortable.
    I’m in a similar situation and I’m bored to tears, but my cash cushion isn’t quite there yet, so I can’t just quit.
    But soon …

  34. beth says:

    I can relate as a public educator so I am transitioning to a 2nd career that still involves teaching but more money and lots of entrepenurial opportunities, very uncomfortable to make changes is a sign I’m on the right track

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