Planning Your Goals

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As we enter yet another new year, now is a great time to set some big goals. I recently formed a new Accountability Group and we met on this very topic.


This is where I got hung up with my 2019 goals. I recently got into OKRs so I was trying to use WeekDone for my personal goals but the system just wasn’t working for me (which, as a coder, makes me want to go out and build my own Personal OKR SaaS). I scrapped that and opened Google Sheets and soon had over 65 rows! I really wanted to use the OKR method to set my goals in 2019, but it was taking up way too much time so I reverted back to the system that I’ve used the previous 4+ years: Trello.

Read more about OKRs in John Doerr’s Measure What Matters or find examples at

I live in Trello. My buddy Alon taught me a great system for getting things done using Trello, and I’ve stuck with it since January, 2017. When I was with FMTC, we used Trello for goal setting. So why was I looking for something else?? Trello it is.

Create a new Board and find an inspiring background. Next, create 5 lists:

  • 2019
  • 2019Q1
  • 2019Q2
  • 2019Q3
  • 2019Q4

Great – now let’s set some goals!

Annual Goals

Think about where you want to be in 1 year. Picture yourself sitting there, reflecting on the year that just passed. What does your life look like? What does your Inbox look like (I don’t care if you’re at Inbox0; what I mean is who’s emailing you, about what)? Who are you? Answering these questions will help you set your goals.

I like to categorize my goals, and I use Trello labels to do this. My labels for 2019 are:

  • Financial
  • Credibility
  • Self
  • Work
  • (SaaS)

Assign each their own color label but avoid using the Black and Green labels. These are reserved for “Missed” (black) and “DONE!” (green).

Tip: get the Card Color Titles for Trello Chrome extension.

You’re not going to get your goals right on the first try. I probably spent 5-6 hours on them over the past week (not including the call w/ my Accountability Group). Even then, they changed a bit after talking with some others. Here are my 2019 Goals:

  • Financial Freedom
  • Be Known as a Thought Leader
  • Better Mental Self
  • Better Physical Self
  • WAH Freelance Programmer
  • Launch (SaaS)

If you’ve done any type of goal setting before, you should be screaming at me right now. Those are TERRIBLE goals! Why? Because they’re immeasurable. I know. This is where traditional goal setting & OKRs are merging in my system. I don’t simply have a goal of “Financial Freedom,” I have a checklist of 7 things in that card outlining what that means. In reality, that card is all about revenue, but the revenue goal, “$xxxk in annual revenue” is not inspiring. “Financial Freedom” is.

When Amy Powell of Resourceful Mommy sets her goals, she includes with them (on the Trello card):

  • Why
  • Obstacles
  • Quotes, Verses & Encouragement
  • Visualization
  • Resources
  • How will I track progress
  • How will I celebrate
  • Habits (a checklist – what needs to be done routinely do accomplish this goal?)
  • Action Steps (a checklist – how do we get started?)

This system is incredible and I’ll be going through my own 2019 goals to fill in these details. Creating goals is easy (despite causing much stress in my life last week) but the daily grind to accomplish the goals is difficult. Amy’s system reminds us why we set these goals in the first place, identifies the obstacles that will try to stop us, gives us words of encouragement to keep going, defines how progress will be tracked (after all, how do you know you’re getting closer to reaching a goal if you can’t track progress on it?) and dangles a carrot in front of us with a celebration.

Quarterly Goals

When eating an elephant take one bite at a time – Creighton Abrams

Now that we know what our lives are going to look like at the end of the year, it’s time to break down these goals into more manageable pieces and we start with our first quarter goals.

If the goal is something linear, the process is quite simple. If you want to read 12 books in the next year, you’re going to read 3 in the first quarter. But many of your goals are not going to be this way – even revenue goals.

Part of my revenue goal includes affiliate income, and I’m in a niche which is huge in Q4, but pretty quiet the rest of the year. So I’m not going to expect 25% of that income in Q1.

Another annual revenue goal includes income from a SaaS – which isn’t built yet. So I can’t expect any income from that in Q1. This is where I go back to Google Sheets and break down revenue by quarter – and make sure when I add it all up, I hit my annual goal.

Other goals are quite linear. If you want to write a blog post each week, you’re going to write 13 in Q1. Simple enough.

As you set your Quarterly goals, make sure you’re not over-committing yourself but also make sure you’re making progress towards your annual goals.

Tasks are not Goals

I had a couple of “goals” that, when I looked at them, realized I could sit down for 2 hours and complete them. Those are tasks, so why did I put them on my goals list? Because they would get me closer to my annual goal. It’s fine that I identified them, but they’re not goals.

I took these tasks and combined them into a checklist on a new Trello card which did represent a goal. Now when I complete the tasks, I can check them off and when all of the items on the checklist are completed, the goal has been met.

Let’s Go To Work!

Leaving your goals on a Trello board, only to look at them 90 days later, is a guaranteed way to miss them. Set up systems and processes that set you up for success.

Winners and losers have the same goal. – James Clear

We can all have goals but the individuals who achieve their goals are the ones who design and install systems to keep them on track.

Discipline = Freedom – Jocko Willink

I have a daily checklist of things I will do every day, and those items are broken down by time of day. An item on that checklist is “After dinner I will plan tomorrow’s meals.” I’m forcing myself to turn meal planning into a daily habit, and removing 6 decisions (what I’m going to eat (yes, 6 meals / day)) from my day tomorrow. When it’s time for second breakfast (my favorite meal of the day) I look at my plan and that’s what I eat. I do this after dinner since my lunch it typically leftovers from dinner, so I can measure and log the food before it gets put away.

So review your quarterly goals and ask yourself, “What’s it going to take to meet this goal?” Set up a system to eliminate excuses and decisions. I use Manifestly because I use it for other checklists, but you may be able to use Trello, Google Calendar, a piece of paper & pencil, or Habitica was recommended to me, too.

Now What?

Take your annual goal planning seriously, create systems to make daily progress, and next year you can look back and smile at all you’ve accomplished. Happy New Year!

  • Sherry Smothermon-Short
    Posted January 1, 2019 12:50 pm 0Likes

    Love this! Goal-setting can be hard especially since there are so many systems out there that we could use. Definitely can confuse you!

    I love the concept of “here is who I want to be” combined with “here’s how I’m going to make that happen.”

    Amy’s list of things she includes is genius! Putting that much thought into your goal sets you up to succeed.

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