The Necessary Evolution of Personal Goals

by Dan Walsh

Goals change as you change with them….

I’ve been a list-writer and goal-setter my entire life. That behavior comes with a whole set of best practices, but I’ve been internalizing a specific one lately: Goals should be allowed to grow and adapt to fit the person you become.

I think there is a general tendency to set a fixed goal, and then remain beholden to it even though you’ve grown out of it. I know I’ve been guilty of this. I added “train with Ninjas in Japan” to my life-list when I was in 5th grade. It took almost two decades for me to admit that becoming a ninja wasn’t really a priority in my life anymore. But in the intervening 20 years I would feel a pang of guilt every time I opened my list and saw the unfinished item. The older me felt guilty for not following through on my younger self’s dreams. But that’s sort of ok. Goals should evolve.

This entire site has been one prolonged exercise in the evolution of personal goals.

Scouring Rust and Delusions of Grandeur

When I first started this blog, I wanted a private space where I could develop thoughts. I didn’t link to it because I didn’t want the pressure of “writing for a crowd”. I also wanted to see if anyone would stumble onto it. If they did, maybe the content was so awesome that my renown would spread across the inter-land and I’d get a book deal out of it. Ha!

All fantasy aside, I hoped the private nature would give me freedom to explore ideas and grind away some of the rust on my writing skills. It worked – a little bit. I didn’t write often however. It felt like a huge chore. I’d get ideas for posts but never write them because it was do daunting. I was a slow writer and I needed more practice.

Building a Habit of Steady Progress

I was inspired to develop a regular writing habit after reading Bird by Bird. I often pressured myself into marathon writing sessions, and maybe I’d be better off with steady, regular progress. I was so inspired that I rearranged my entire schedule so I could wake up an hour earlier everyday and devote that quiet morning time to writing.

I won’t lie. It was tough in the beginning. It was hard getting up. It was even harder to jump into “writing mode” on command. Bird by Bird had prepared me for this though. I knew the most important thing was to just sit at my keyboard for an hour – even if everything I produced was crap. No Pressure!

I eventually developed a routine, including a warm up, that helped the words flow more naturally. This writing hour became habit and one of the most important times of my day. In fact, my days now felt wrong if wasn’t able to write for an hour.

I was diligent about this morning writing time. I didn’t know what to write about at first, so I recorded my earliest childhood memories. Then I dabbled in short fiction for a few weeks. Then I tackled some big topics that I’d wanted to write about for a long time. One hour every day. Even on the weekends. The goal was to craft these ideas into well polished short stories or blog posts and get them up on In this manner I made steady, private progress for a few months.

My habits were formed, writing was enjoyable, and I was steadily becoming more proficient.

Real Artists Ship

My friend Victor triggered the next evolution of my writing goals. One night over dinner he asked me what was new. I told him about my recently acquired writing habit. He asked where this writing was and why he hadn’t seen any of it. It was at that moment that I realized I was waiting too long to release anything. Perfect is the enemy of done, as they say. By keeping all my writing private I was in a way giving myself permission to never finish any of it.

In fact, most of my “writing time” was spent deliberating over what to type, or editing what I had already written. I needed more volume and I needed to separate the editing process from the writing process.

To remedy this I set a goal for myself to write one post every day for 30 days. It was hard – really hard – but I accomplished it. I learned many invaluable writing lessons during this month.

  1. Sometimes I had to break one post into two shorter posts so I could publish.
  2. I realized most of my “blog topics” could fill a book and that I really needed to chunk them down. No wonder I never finished anything.
  3. Writing honestly, with no pomp or pretense, is hard but completely worth it.
  4. I discovered how much I could actually write in an hour.

Most importantly, I developed the attitude and ability to say “Oh well, there’s always tomorrow.”

If I wasn’t happy with my writing from a given day, I had no choice but to let it go. This requirement instilled a sense of iterative progress in me. It didn’t matter if I was unhappy with what I wrote today, because I could try to improve tomorrow. That next post might be amazing. The quality of my output was no longer tied to individual posts. Instead, it was reflected by my entire body of work. This seems like a minor distinction, but I cannot overstate its importance. Internalizing this lesson opened my eyes to all kinds of possibilities and has magically given me a universal map to all of them. Progress and success are products of iteration

30 days of straight shipping felt great. I improved so much because of the added pressure and it was no longer intimidating to make my writing public.

Momentum and Burn-Out

The benefits of writing and posting everyday were so profound that I wanted to keep up the practice. Just imagine, after a year I would have written 365 posts! That was crazy to me. I genuinely enjoyed writing at that point, so it wasn’t a huge sacrifice to continue to publish a post everyday. I wanted to continue to improve my writing and I finally wanted to get all those “great blog post ideas” out in the wild.

I kept up the pace and even hired an editor for a short time to kick my writing up a notch. But after a few months I started to get burned out. I still wanted to write everyday, but I was having a hard time coming up with topics that were interesting and short enough for me to tackle within my one hour writing window.

My writing sessions became a source of anxiety for me. They used to instill a sense of accomplishment, but as it got harder to write they felt more like failure. Is this writer’s block? I don’t know.

For better or for worse, I was forced into a short hiatus. I started teaching a night class and I frequently got home too late to even get a full night’s sleep, let alone wake up early to write. When I forced myself out of bed I was barely awake enough to get dressed let alone write something intelligent. I struggled with this for a few weeks before I gave in and allowed myself a writing break.

Betraying Former Goals

My class finished a few weeks ago and I feel refreshed from the break. I’m back in the habit of writing every morning and it feels great. I have one problem though: I can’t seem to publish everyday.

Now that I’m back, my tendency is toward larger topics that require more words to fully articulate. This post is an example. There’s no way I could do this topic justice in only one hour, but these are the kinds of topics I want to write about now.

This feels weird because publishing daily is such an ingrained goal. If I don’t publish a post everyday I get anxious. It’s hard to concentrate on other tasks until I finish. I even mentally compose sentences in my head while others are trying to have a conversation with me. It’s bad!

But I need to be ok with allowing my goals to change and evolve so that I can change and evolve too. I’ve already gained the benefits of writing many posts, so now I need the growth that comes from writing excellent posts. This isn’t a criticism on my former writing, just that “one post a day” shouldn’t be my priority any more. My priority should be to say what I want to say. I need to give myself the freedom and flexibility to pursue the topics that have become important to me. This change makes me feel anxious. But in retrospect, so did every other time I shifted my writing goals.

By necessity, goals need to change so that growth can continue. There’s no reason to stick with a goal just because my younger, less-wise version of myself thought it was important.