Stepping Off the Path of Least Resistance

I’ve been writing here for a year and a half.

While I missed my initial goal of posting twice a week every week, I have published over 100 articles.

But upon reflection recently I found a problem.

How can I teach others to optimize their lives if I am not optimizing my own?

I am doing well in a number of areas. I am good with money. I am very efficient and productive. I have learned a great deal about the inner workings of happiness.

These are the areas in which I have focused my writing.

I have stated before that part of why I continue to write this blog despite having a million other things going on in my life is that it performs multiple goals. It helps others. It pushes me to become a better writer. And it forces me to continue learning.

This is still true. But I have recognized that I am learning only marginal improvements on things that I am already good at. That’s not an efficient approach to self-improvement. That’s not a good 80/20.

I need to step out of my comfort zone and work on my weaknesses.

Finding Truth in Fiction

Two years ago I started a creative writing group.

I gathered a bunch of friends with a creative streak that work in fields other than writing. The idea was to build a creative outlet for people that otherwise may not have much of one. Myself very much included.

Someone creates a prompt, anywhere from a broad theme to specific instructions to a poem or song, and everyone gets two weeks to write a short story. We share our stories and the next person in line creates a new prompt. Two weeks is long enough to write something, but short enough that you don’t have time to get in your own head about it. It forces you to brush off perfectionism and just write something.

If you don’t write fiction at all, I would encourage you to start.

Fiction allows you to get into your own head in a way that non-fiction writing, or even journaling, does not. You are not trying to learn about yourself, but it happens anyway.

One recent story that I wrote highlighted to me that I am uncomfortable with how I have lived much of my life.

The Path of Least Resistance

For most of my life I have followed the path of least resistance.

I want to be clear right off the bat here that I cannot complain about the results.

I have a strong sense of curiosity and equally strong desires to learn and help others. This has made the path of least resistance far more fruitful than anyone could realistically hope for. But it is still the path of least resistance.

I found that I could get good grades in school without effort, so I didn’t put in the effort. I got into a good college without trying hard in high school. I got into a good law school without trying hard in college. I got good enough grades in law school without putting much effort in there, either.

I went to law school not because of a strong desire to try cases, but because of a strong interest in politics and government. Just as importantly, I scored high on a practice LSAT without studying.

As I said before, I cannot complain about the results. I have a great job with a solid salary and a fantastic work/life balance.

But it is not an intentionally designed life.

Behind the Scenes in My Dating Life

I was never a great boyfriend.

Part of that was just being young and not knowing how to be better. Most of it was probably the path of least resistance mindset.

I was never a horrible boyfriend. It wasn’t about abuse or cheating or anything like that. Mostly I would mentally and emotionally withdraw when things got difficult. I had a handful of long-term relationships and most of them ended this way.

After what turned out to be my last break-up, I forced myself to stop and think holistically. Where was I in my romantic life? Where did I want to go? What did I need? Want? What was worth working hard for?

Soul searching ensued and I had the standard romantic comedy epiphany that what I was looking for had been right in front of me all along. I wanted to date, marry, and start a family with a woman that was a close friend of mine. All I needed to do was let her know and then we could live happily ever after.

So I asked her out. She said no.

Hm. That’s not supposed to happen.

I had decided that this relationship was worth working for. I also didn’t want to be that creepy guy that repeatedly asks a woman out only making her more and more uncomfortable. I told her that I would not bug her, but that I would wait for her.

In the meantime I set about making myself someone more worth dating. Self-knowledge. Self-improvement.

Somewhere around six months later she asked me out. This is where the romantic comedy fades to credits or ends on a montage showing our wedding along with short clips wrapping up loose plot lines of minor characters.

That skips over a lot of life, though.

I had decided that this was something worth working for. I reminded myself of that often. I kept working. I kept finding weaknesses and areas that I needed to improve. I kept looking for ways to be a better significant other.

I still look for ways to be a better husband. I will never be perfect, but I will always keep working at it.

I determined what I needed. I decided what I wanted. I devoted myself to working constantly and consistently towards that goal. With regards to my family life, I got off of the path of least resistance and continuously work to stay off of it.

Now I want that for the other parts of my life.

Optimize Your Life

A significant part of optimizing your life is knowing what you want out of it. Another is taking a systematic approach to get there.

That’s what I plan to do going forward. That’s what I plan to write about in 2018.

So here’s the plan:

Every month will have a theme. We’ll start in January with life design. Where are we in life? Where do we want to go? How do we get there?

We’ll continue on from there into other important themes involving issues like money, happiness, and productivity. I’ll continue to include articles written from positions of strength, but I’ll also include experiments and exploration to shore up areas where I am weaker.

I want to do things that are hard for me. I want to put myself in positions where I can fail. I want to work through fear and anxiety. I want to ask for help.

Join Me!

I also want to know what you want to learn in 2018. I want to know what your weaknesses are. Where you feel that you could use some help. I want to know these things both because I want this blog to continue to be useful to you, but also because haring from others helps us find our own blind spots.

Please let me know in the comments what you want to see, learn, and try in 2018. If there’s anything you don’t feel comfortable leaving in the comments, feel free to shoot me an email at

Speaking of email, I just started up a new email list that you can sign up for right after the next paragraph. The old list is the automatic wordpress list, where you will get sent a copy of each new article as it posts. The new list will be actual emails from me.

I want to use this list as a way to keep in touch during the month off as well as start some one-on-one conversations with readers. The emails will be more conversational than the articles and I will respond to any replies that you all send me. Even after relaunching in 2018 I will keep sending emails separate from the posts and hopefully having some good conversations with you all.

Subscribe to our mailing list

On to 2018

I do also have another reason that I want to work on being the best version of myself that I can be in 2018.

My wife and I will be welcoming our first child in February.

This is a very exciting and hectic time in our lives. I want to be sure that I am making the most that I can out of my time and living the life that I want. I have no doubt that it would be very easy to get swept up in the path of least resistance again this coming year. And I’m sure that would be a fine life.

But it wouldn’t be my best possible life. It wouldn’t be the ideal life for my family.

It wouldn’t be an optimized life.

See you all in the new year.

34 thoughts on “Stepping Off the Path of Least Resistance”

  1. I’m subscribed to the new list. I think this is one of the most unique and motivational blogs on the net. I can’t wait to see what you come up with next. This post about focusing on weaknesses and getting out of your comfort zone is something that everybody can relate to. Along these lines, The topic I’d love to see you cover is “risk” in general. I believe many of us would all live happier lives by taking more risks. Unfortunately, taking risks is very hard. A financial example would be taking a significantly lower paying job as a way to maximize happiness or improve long-term career growth. There are many non-financial examples as well. What are the steps to take to take to make an optimized decision rather than live the path of least resistance? I’d love to hear your take.
    Jason@WinningPersonalFinance recently posted…The World’s Least Fascinating Personal Finance BloggerMy Profile

  2. Congrats to you and your wife! As Brian said…parenthood definitely forces you to prioritize things in your life. It’s an exciting time and stage in your life. Also, I’m sure others have said it…but enjoy some time alone with your wife because it’s gonna be hectic when the new addition comes a long! =) Man time flies…my two little ones are 4 1/2 and 16 months! I know it’s cliché but cherish those moments.

  3. Well said and bravo on the upcoming birth!
    I really like this introspective style of writing and will be looking to write in a similar way during 2018. It’s really been great to get exposure to the ideas of you and other thoughtful folks in the community. Keep up the great work so we can all push each other! 🙂

    1. Thank you very much. Pete from Do You Even Blog wrote after returning from FinCon that he believed 2018 would be the year of authenticity and transparency in blogging, and I think he may be right. That’s at least the direction I’m working towards and sounds like you are as well.
      Matt recently posted…FinCon and a New DirectionMy Profile

  4. Congratulations Matt!!! That’s such great news! 🙂

    I am sooo looking forward to your challenges and experiments in 2018! I think we all tend toward the path of least resistance. Your not alone there. But there is much to gain from stepping it up and out of our comfort zones. As my

  5. If you want adventure in your life, have children! So happy for you, Matt. You’re going to be a great father. As far as 2018 goes, I want to see posts on how to finish a book you’ve been working on and off for a year and half. I also want see posts on how to build a home without going insane. So if you can focus your blog on these two things, I’ll be best bud forever. I’ll even buy you a beer (or two or three or four…) at FinCon 2018.

    1. Thanks, Mr. G! Strangely enough there may be a bit on writing a book. I’d like to take a stab at long form fiction and will be considering a novel among my possible 2018 goals. Either way, there will definitely be an exploration of setting and achieving big goals.

      As to the house, I think I’ll have to bow out. Considering that I am starting a one-year lease on a new apartment this week, I don’t anticipate that I will have any home-building experience in 2018. Would still love to grab a beer at FinCon, though!
      Matt recently posted…FinCon and a New DirectionMy Profile

  6. I love the theme of this post, Matt! Recognizing that you are taking the “easy way” makes it easier to step off that path. And the sooner, the better if you want to make big change. I think you are right about being happy with what you have accomplished, but moving from “good to great” takes a different look at how you are living life. So excited about your new year and all it will involve!
    Vicki@MakeSmarterDecisions recently posted…Scaling Up Our Lake House RenovationMy Profile

  7. Congrats on the baby!

    When you mention “How can I teach others to optimize their lives if I am not optimizing my own?” that sounds like imposter syndrome talking! Most people aren’t thinking about optimizing their lives at all, or being aware of times when they aren’t. I think you’re doing fine. 🙂

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