Over the summer on Twitter I asked, “Do you have a roadmap?”
(Do you follow me on Twitter yet? You should, please come say hello!)
Roadmaps are super useful and common among projects in the tech space. What I was really curious about, though, was how many people have roadmaps โ a list of goals and a plan to achieve them โ for themselves. So many smart people showed up to share knowledge, tools, and experiences! And just as many folks said they didn’t have a roadmap or didn’t know how to create one.
(Shout out to Eric a/k/a Second Realm for a comprehensive, step-by-step and to Kreature Kastle for recommending the Notion app, into which I’m typing the draft of this post!)
I mean, I have #lifegoals and thought I was doing a pretty good job writing them down and adjusting them every quarter, but when I dug into that process over the summer I felt like I hit a wall. My Big Dream hasn’t changed for over five years and I don’t feel much closer to reaching it than I did when I first created it. Maybe a tiny bit closer thanks to NFTs.
Big. Effing. Mood.
Goal domains
You can set goals for just about anything, really – work, financial, family, parenting, spiritual, emotional, physical, philanthropic, learning, etc. One of the most common rules you hear about goals is that they must be SMART – Specific, Measurable, Attainable, Realistic, and Time-Bound. Basically your goals should include what you want to do (specifically) and by what date.
I’m of two minds on the Attainable and Realistic bits of SMART goals. What’s attainable? What’s realistic? They’re such subjective standards that in the end those terms mean nothing – really odd when the whole point of SMART goals is to be specific, right? And what’s attainable and realistic for one person might not be for someone else. How do you even know what’s attainable until you try?
On the other hand…
You can squish your goals down so they’re attainable and realistic if you’d like to, but in my opinion…pffffft. Who wants realistic and attainable top-level goals? Why not go for a little strettttttcccchhhh and pursue something you really, truly want rather than settle for what you think you can accomplish?
Because like, we’re all capable of accomplishing more than we think. We underestimate our knowledge, skills, and talent SO MUCH.
All of this being said, you know best how your brain works, what motivates you, and what stresses you out. If deadlines give you hives, make SM goals. If you’re a big picture thinker and like to follow your interests, make ART goals. Pick your letters or just throw them all in the bin, you don’t need to set goals at all.
If you do set goals, though, it’s a good idea to become BFFs with them. Get in there with your microscope and tweezers and make sure they stand up to scrutiny.
Questions to ask yourself
- What does accomplishing this goal look like?
- How will I feel when I accomplish this goal?
- Why do I want to pursue this goal?
- If I don’t accomplish this goal, what will my life look like in five years?
- What actions would I need to take to accomplish this goal?
- What kind of person would I need to be to accomplish this goal?
- What habits do I need to cultivate to achieve this goal?
- What obstacles might I face pursuing while this goal?
- If I face obstacles, what will I do?
- What tools and supports do I need to accomplish this goal?
- What do I need to learn to accomplish this goal?
I recommend writing your responses to all of these questions for each of the goals you’ve identified, for reasons which will be come clear in like two seconds.
Ok, so now what?
It was a lot of fun playing 50 questions with yourself, yeah?
I hear you. It’s lot of work! Give yourself a pat on the back for doing it. โค
The best thing about answering the same questions over and over again as you move through each of your goals is this: each goal presents different challenges and obstacles, so you end up with a huge list of creative ways to handle them. That’s a lot of new resources in your creative toolkit that you can apply to any challenge you face. You might find it helpful to make a master list of things you can do when you get stuck and post it where you can easily refer to it.
Did any of your answers change how you think about your goals? Do they need adjustment?
The good news is goals don’t take it personally when you want to change them. They’re just words โ your words โ you can do whatever the hell you want.
I’d love to tell you want to do next but…I don’t know! I haven’t gotten that far yet. No worries, I’ll keep writing through this because it helps me clarify my thinking. Maybe it helps you too?
I think the next thing I need to do is type my notes and see if I notice any common threads. Maybe there are some supports that I will need for some goals. And I’ll look for ways some of my goals can support others.
I’ve only worked through my top level, 6 month to 1.5 year goals. I’d set out to do all one-year goals but some of the things I want to work on will take longer and others need shorter deadlines.
People I admire who inform my thinking about habits and productivity:
- James Clear (Atomic Habits)
- The Nap Ministry
- Darren Hardy (The Compound Effect)
- Ryder Carrol (The Bullet Journal Method)
- Charles Duhhig (The Power of Habit)
- Stephen Covey (The 7 Habits of Highly Effective People)
- GaryVee
Also, very highly recommend the InnerGuide Life Coach in-a-Book. It’s a 90-day goal planner full of helpful journaling prompts and gentle nudges. This is my third January working with one and it helps me stay on track so much. The trick to using this planner is to keep your top-level goals in mind but focus on very small actionable steps.
Hope all of this was helpful in some way! I’m always up to chatting about goal setting and such so feel free to drop a comment or hit me up on twitter @jenjustjen3 !

Leave a Reply