How I went from a hot mess to an organized professional

I used to scoff at goals, resolutions, and aspirations. Life, it seemed, was too full of random chaos. It’s what happens while you’re making other plans, right?

There were big things in my childhood that were out of my control. My dad left. My grandma died young of cancer. My mom devolved into serious mental illness. In the face of these inevitable realities, I learned to give up on the idea that I could control anything at all. I learned resilience and good humor in the face of adversity, but I did not learn how to make plans.

Some kids with chaotic childhoods go the other way and develop type-A perfectionism as a coping skill. I slid toward “why bother” instead. By my teens, I had stopped trying to perform academically or hold onto any hopes for my future.

Of course, I did make plans. I got out of my hometown in Idaho and went to art school. I got a job, and then another, and so on, and over thirty years I have built up a career. But most of what I have accomplished has been reactive rather than proactive, because reactivity is how I learned to cope.

I am not a planner person

In the 1990s Franklin Covey had a retail store in Downtown Seattle. Whenever I walked past I was drawn inside by some mysterious pull. There was a part of me that wanted to make plans. I wanted to have structure and lists and goals.

I could not afford Franklin Covey products, and whenever I bought a cheaper day planner from the University Bookstore it sat abandoned. I could never figure out what to put in there, or how to make it useful. I would write down some aspirational goals for my health, career, or social life, but I could never figure out how to take the right actions to make progress. I abandoned my lists and fell back into self-comforting behaviors. Somehow, life went on anyway.

We all come to adulthood with our particular challenges. My childhood traumas left me with depression, anxiety, focus problems, and a sense of hopeless apathy. I was not the kind of person who could get organized, even when some part of me wanted to.

STEP ONE: Unpack your baggage

PLEASE NOTE: You do not need to modify yourself to fit a productivity system! But you may be able to modify a productivity system to fit you.

Not all of us find planning or achievement-oriented thinking easy. If you are carrying trauma or dealing with any sort of neurodivergence (or happen to be human), you may find “productivity systems” to be somewhat hostile.

Before planning anything, it is helpful to go through a review process to understand what is already working and what you want to change. This may be a straightforward accounting of things that are working well and a few things that need attention. Or it could be an existential crisis. If the latter, you may need some support or therapy to get to the bottom of what is keeping you stuck.

One question to answer before making a plan is: what do I want to change in my life? If the answer is “nothing, really,” then all you need is a system for keeping the lights on. But I’ve never met a person who did not want to change something, and if you want to change you need a plan.

STEP TWO: Evaluate your balance (or lack thereof)

In our culture, we tend to hoard projects, to-dos, activities, and stuff. Part of living in consumer capitalism is being valued as a consumer. That means we have strong cultural messages encouraging us to ADD MORE to our lives if we want to be happy.

Even those of us who try to be aware of this or embrace minimalism get caught up in acquisition. I own a shocking number of Udemy courses that I haven’t started and an alarming collection of colored pens. And black pens. And art supplies I rarely use. These all represent things I care about, but buying more of them doesn’t usually lead to the progress I want.

Likewise, I keep adding things to my calendar to try to compensate for my lack of community. I have a memoir buddy, a sketching buddy, a massage therapist, a women’s group, as well as dozens of people I would like to see more but can’t find time to schedule more social time without totally depleting my battery.

I am hosting an Equinox Planning workshop this fall to go through a process of rebalancing and letting go. Part of this process is documenting where my energy and time are going and deciding what to let go of (for now). Arguably the most important part of planning is deciding what NOT to do in a given time frame.

STEP THREE: Decide what’s important (for now)

The tendency to hoard projects is a function of not having a good way to decide what your priorities are. We tend to think everything is more or less equally important and end up with more on our list than our brains can cope with. This leads us to default to what’s urgent and indefinitely procrastinate all of our equally important projects.

Here’s the thing. You can keep an infinitely expanding list of things you may someday like to do, but you don’t have to work on all of them at the same time. I have found that keeping three to five projects on my active list keeps me moving forward on them.

To keep your projects manageable, try to define work that can be done completely in 2-3 months. Of course, some projects are bigger than will fit into a few months, but if you can break big projects into smaller pieces, it will help you gain momentum. Once you have all of your wild aspirations chunked into juicy, doable plans…pick any three.

By focusing on only three projects within a given time frame, you have a good chance of keeping all three moving forward. As soon as one is finished, you can add a new project from your backlog. If something more urgent comes up, you can press pause on your projects until the urgency has passed.

I wish I could say that I always have only three projects on my plate. I have gotten better about having no more than a couple of personal projects in play at any given time, but my day job tends to stack up projects on top of each other. To manage this, I set priorities on a seasonal, monthly, weekly, and daily basis.

STEP FOUR: Block out your priorities and habits

Some things cannot be turned into projects. Habits like healthy eating, exercise, or even small things like flossing and loading the dishwasher are aspects of daily life that have no endpoint. While certain habits may support your projects, most are simply what make up your life.

The best way to maintain the habits you want is to make them as easy and automated as possible. There are plenty of books, blogs, and podcasts focused on habit formation, so if you find habits a challenge you can find plenty of resources (Atomic Habits is a great place to start).

When you want to form a new habit, the best strategy is to focus on one at a time for at least a month. If the habit is simple (like flossing), you can attach it to a habit you already do daily (maybe brushing your teeth?) and then keep track of whether you did it or not.

Eventually, a simple habit will start happening on autopilot, and you won’t have to use reminders or trackers. But you may not get there for months, so the trick is to not give up if you forget now and then. It takes time and persistence to form a habit.

More complex habits like healthy eating or exercise take longer and require mini-habits to start programming into your routine. Simple habits like “find one recipe” or “put on walking shoes” can be repeated easily to start these larger lifestyle changes.

Once you have a stack of habits built, make sure you have blocked out the time to practice every day. Habits don’t have to happen daily, but they will stick better if done more often. I find it helpful to have a morning routine and a bedtime routine to bookmark the day. It is also helpful to have a workday shutdown routine. These are all opportunities to create sequenced habits that can become largely automated.

To move projects forward, you will need to block out time in your schedule to actually work on them. Creating a project plan without time to work on it is as useful as making a wish.

I don’t like having a fully scheduled day, but I find that the process of blocking out my day increases my odds of doing what I intended. The times don’t matter as much as the process of seeing what will fit in the day. Try creating a time block plan around any meetings or appointments that includes your daily habits and longer focus sessions for project work. You can use a paper planner, a digital calendar like Google Calendar, or just draw it on a Post-it note or a scrap of paper.

STEP FIVE: Review and adjust

This may be the most important step. No matter how good you are at planning, things will not go as planned. Let me repeat that: Things will never, ever go as planned. In the words of Dwight D. Eisenhower, “Plans are useless, but planning is indispensable.”

If plans are useless, why bother making them? Plans are like compasses, and they let you know whether you are going in the direction you intended to go. Without a plan, you are wandering, aimless. But for a plan to be like a compass, you need to check it frequently.

One of the pillars of David Allen’s GTD system is the weekly review. In this process, you look back on what you accomplished and make some kind of plan for the following week. This is an opportunity to adjust your direction if you are off track, and it is also an opportunity to decide on a different route.

Persistence and staying on course will lead to completed projects, but minor adjustments along the way will lead to better outcomes. A review process keeps you out of the productivity trap of simply checking items off a list and adding more to the same list. By the time your project is complete, the way you got there can and should look a bit different than you had planned. Changing direction means you’re learning.

Be an underachiever

One final tip for the chronically busy over-planner: Be an underachiever. Those who attempt to do less do more and do it better. In your weekly or monthly review process, try to remove as much from your list as you can, until it only contains the projects and habits that represent your best life.

Clearly, there are some unwanted tasks and projects that are requirements for work and life to run smoothly, but remember that these are optional, too. On some level, you are choosing to do them because you want to keep your job or maintain marital harmony or be able to find matched socks. But you don’t have to.

The more you can delegate, defer, or delete unimportant projects and tasks, the more time and energy you will have for the things that you care about. This is the secret to doing more and making a more significant impact in the world: Do as few things as possible, but really put your whole heart into what you do.

Join me for Equinox Planning

Do you want to shift your habits or finish more projects? Do you feel like your life is too full of tasks, meetings, or random thoughts? Join me for an Equinox Planning session to learn my system for keeping my life in balance and projects on track! These workshops are totally free and happen twice per year, in the spring and fall. Just add your name to my email list to receive invitations.