The purpose of this blog is to enable readers to adopt a low cost of living, work fewer hours and gain free time. But for those of us who have managed to do that, sometimes the question of what to do with all that free time can feel intimidating.

Preserving some free time purely for leisure is crucial for happiness and well-being, and I’ll talk about leisure for leisure’s sake in a future post. But for me, the most alluring aspect of this lifestyle is my ability to spend my extra time, energy, and money on passions, projects, and schemes.  Currently, my “outside of (paid) work” projects include studying Spanish and writing this blog, and I’ve also been running, swimming, and biking a lot because I’m interested in training for and competing in a triathlon sometime next year.

Sometimes, discovering passions and selecting projects to work on is simple; training for a triathlon feels like the natural and logical continuation of things I already love and do on a regular basis. In other cases, the selection process can be more difficult. The concept for this blog, for example, was born out of an enormous degree of introspection and personal work.

This week, I want to talk about means of unearthing your deepest dreams and goals and creating a roadmap for achieving them.

Step One: Learn about yourself to set intelligent and fulfilling goals.

At the beginning of this year I felt stuck. I was bored in the studio and experiencing some physical problems related to throwing pots, and I was considering career change options. January through March is my “slow season,” so I decided to take a couple of weeks off from work to do some self-reflection.

I took a short online course offered by writer Patti Digh focused on making big leaps in your life; I also read Wishcraft and What Color is Your Parachute and completed the exercises they contained. Some of them were dopey, as self-help activities can be, but others were helpful and illuminated desires of which I had been previously unaware. For example, when I began I thought that I wanted to get hired full time by someone else, but I quickly discovered that for the time being,  working for myself and preserving my free time were vitally important to me. I also realized that I love teaching groups, something I never would have anticipated.

The concept for a prescriptive nonfiction or “didactic” type blog about living simply and working less was one result of this work.

(In addition to the books I mentioned above, two other self-inventory tools that I like are the Enneagram and the MBTI, both personality typing systems. You have to pay to take the “official” tests, but free and thorough tests can be found online.)

Step Two: Brainstorm a broad list of possible goals.

Put in your earbuds, pick some music, set a timer for an hour, and grab your favorite notebook and pen. Think of it like a freewriting exercise: write as many goals as you can think of, without self-editing or questioning your ideas. Don’t worry; no one expects you to complete all of them. You’re simply giving yourself an abundance of enticing options for when it comes time to winnow your list. This can be a fun exercise to complete in a group; I’ve had great success leading it outside in a field on some blankets on a sunny day. 

If you’re struggling to generate ideas, try breaking up your list into 1-year, 5-year, and lifetime goals. Alternatively, break your list down into categories such as Health and Wellness, Adventure and Travel, Money and Finance, Relationships, Skills, and Knowledges. While you’re writing, keep in mind the things you learned about yourself during the personality inventorying you completed in step one.

Once the initial hour is up, carry your notebook and pen around with you for a couple of days. I guarantee that additional goal ideas will come to you unbidden while you’re cooking dinner, falling asleep, brushing your teeth, or eating breakfast. Write all of these down as well.

Step Three: Narrow Your Focus

Once you’ve generated a lengthy list of goals, it’s time to focus your attention. I like to run through my list, starring any goals that jump out at me, and then dividing those goals once again into 1-year, 5-year, and lifetime categories, creating a sort of “shortlist” and narrowing my choices significantly in the process.

Finally, put your curated 5-year and lifetime lists aside, (they can be examined and curated again before you begin working on them) and carefully select the goals that you want to work on in the immediate future. I recommend narrowing your list down to between 1 and 3 large goals that you want to be working towards right now. (Smaller immediate goals, things that will take a weekend or an hour a month can find space on this list too.) If you’re struggling, as I often do, to make your final cuts, try asking yourself the question “what keeps me up at night?” This litmus test often helps me to illuminate the goals that are truly important to me, as opposed to goals that I might feel like I “should” set. If you previously divided your list into subject categories, you might also consider making your final selections from different categories to provide some breadth and variety.

Business-y types love lecturing people about the importance of  “SMART” goals (Specific, Measurable, Achievable, Realistic and Time-Bound). I don’t think you need to get that fussy with much of your goal-setting, but I do believe it’s important for you to know when you’ve completed a goal. Many first draft goal lists contain imprecise objectives like “become an artist” or “travel internationally.” I would challenge you to nail down your finals goals and make them very precise. For example, “become an artist” could be improved to read “pay all of my bills from the profits of selling my paintings,” or “find a studio and an agent to represent my mixed-media sculpture.” In addition to providing a “cap” so you know when you’ve completed your goal, this process of refinement also enables you to define and clarify to yourself exactly what you’re trying to achieve.

Step Four: To Begin, Just Begin.

In a previous post, I talked about the “Ready, Fire, Aim” method for getting things done, and I want to revisit it here. Once you’ve narrowed down your list to 1-3 goals you want to work on in the immediate future, the best thing you can do is pick the one that tickles your fancy the most and start working on it Right This Minute.

If you want to build a website, do a quick google search for wordpress templates and make a list of three that you like. If you want to travel in Spain, start pricing tickets on skyscanner. If you’re interested in learning to brew beer, look up the address of the local brew shop and drop by. At this point, you’re trying to find out what you don’t know in order to illuminate your path to completing your goal.

Crafting a goal list that you feel excited by and then allowing it to stagnate because you’re overwhelmed and you don’t know where to begin is regrettably easy. By doing something- anything- that moves you closer to your goal, you create momentum that compels you forward.

Step Five: Create Your Roadmap

While starting before you’re ready can kickstart your goal progress, most large goals will eventually require some planning. Use the research you completed in step four to create a sort of “shortlist:” the next 3-5 steps that you’ll need to take to start making progress, plus the date by which you want to have these steps completed. For example, if I’m interested in traveling in Spain and I’ve already looked up flight costs, my shortlist might look something like this:

To Do: Spain Adventure (Complete within 1 week of August 1st)

  • Research living costs in Spain
  • Create trip budget
  • Order lonely planet guidebook
  • Select travel dates/trip length
  • Post to facebook looking for travel buddy

The more specific each of these steps is, the more likely you are to succeed. Once you’ve completed the steps on Shortlist #1, you’ll often find that the next few steps on the path will be illuminated for you. Depending on the complexity of your goal, you may be able to rinse and repeat the shortlist step- creating a second shortlist and completing it, and then a third- until you’ve reached your goal.

More complex goals can benefit from more involved planning; if your goal contains many steps or deadlines or moving parts, consider using the “reverse mapping” technique. Barbara Sher discusses reverse mapping in her book “Wishcraft,” but in brief, you start with your goal and work backwards, creating a task list that begins with the last step necessary to complete your goal, and then the second to last step, until you eventually “map” your goal all the way back to step one.

The Long Haul: Procrastination, Habit Formation, and Quitting

If fear or procrastination regularly prevent you from completing the tasks on your list, you’re not alone. If you struggle to get started, I recommend committing to a tiny amount of work; pick the smallest, simplest task that you can conceive of, and then sit down and do it right away. If your plan is to create a trip budget, commit to sitting down, opening a google spreadsheet, and titling it “Trip Budget”. That’s all. I wager you’ll find (as I often do) that the act of putting butt in chair is a powerful motivator; once you do it, you might just find that you’re compelled to continue. In the words of Steven Pressfield: “There’s a secret that real writers know that wannabe writers don’t, and the secret is this: It’s not the writing part that’s hard. What’s hard is sitting down to write. What keeps us from sitting down is Resistance.” (I highly recommend Steven’s fabulous book about the creative process, titled “The War of Art.”)

Try to carve out a chunk of time (an hour? 30 minutes? whatever you can spare) at the same time every day to work on your goal(s). This habituates you to the process of sitting down to work, and also makes it less likely that you’ll forget or flake out and watch Game of Thrones when you intended to be productive. If you find yourself avoiding a particular task, move it to the very top of your to-do list and complete it first. It’s kind of like they say in yoga: when you feel resistance toward a certain pose, it’s often the one that your body really needs. I guarantee that you’ll feel better once it’s done.

Finally, don’t be afraid to let go of goals that aren’t working for you. The time that you’ve committed to a goal is a sunk cost; you’re not going to get it back no matter what. Sometimes we get started working on a project that we think we’re interested in, only to realize that the reality doesn’t stack up to our expectations. Better to throw that goal back like a small fish and choose a new one than to continue slogging away at a venture that doesn’t fulfill or intrigue us.

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