I’ve taken a lot of time off since I first started school at Stanford, ranging from periods of 3 weeks to an entire year.
My freshman year of college, I was in 3 clubs, a Division I sports team, and way too many classes. I felt overwhelmed and alone, especially since every other student was stupidly smart and on top of their shit (or so it seemed). I was working myself to the bone even though I didn’t have a clear idea what I was working towards and why.
In the beginning, I took time off because I felt burnt out from a hectic college schedule. However, along the way I came to cherish these opportunities to introspect, explore professional and personal interests, and learn new skills.
Taking time off was the best decision of my life because I determined the direction I wanted to take and gained concrete skills to move in that direction.
By designing and executing a thorough plan of action, I gained much needed clarity during my gap year. I also gained concrete skills that ranged from managing an e-commerce store to programming a web application.
For those of you fortunate enough to be at an introspective crossroads, I want to share how to achieve ambitious goals when you have abundant amounts of unstructured time. Whether you are taking a gap year in college, in between jobs, or simply in a self-reflective mood, there are organizational tools that can help you effectively manage your time.
Here is how to structure an unstructured life:
1. Set an ambitious roadmap
2. Execute the actual day-to-day
3. Stay accountable and remember to self-care
I am currently taking my senior fall quarter off to focus on my passions, and will be using this two month period as my example.
Step 1 — Set an ambitious roadmap
Brainstorm what you want to do
The few months leading up to my 2 month productivity period, there were ideas constantly floating around my head for what I wanted to work on. Some were related to organizational management and startups, others were related to blog post concepts. I pulled on these threads and dug deeper. Since I knew I wanted to write, I read Medium articles and wrote messy drafts for articles like this one. Because I am interested in tech and startups, I read about tech companies like Tesla in my free time.
There’s a lot of questions you can ask yourself to get your brain going:
- What ideas are constantly floating in the back of your mind?
- What have you wanted to do but were prevented from doing because of your previous schedule?
- Where do you want to be 5 years from now? What skills do you need to do so?
- What activities do others do that make you feel a little envious?
- Who are the people that you admire, and what do they do?
How do you like to brainstorm? Is it by talking to your friends, thinking in your free time, reading for inspiration, or writing down notes? These simple acts of preparation are like preheating an oven before baking. They are essential for when the time comes to set and execute your goals.
Set personal OKRs
Popularized by my dear friend Googs, OKRs are made up of an Objective — a clearly defined goal — and key results — specific measures used to track achievement of that goal. The beauty of OKRs is that they are designed for you to set ambitious goals. You are doing OKRs wrong if you successfully complete all of them!
The goal of OKR is to define how to achieve objectives through concrete, specific, and measurable actions. Each Objective has 3–5 key results and each key result should be measured quantitatively. At the end of the 2 months, you evaluate your success by grading each key result from 0 to 1.0 (1.0 is best) based on the degree to which it has been accomplished. A 1.0 on all OKRs is actually bad because that means the goals were not ambitious enough! An average score of 0.6–0.7 is the sweet spot. OKRs were originally meant to be used in an organizational context, but I find them equally useful for managing my own time.
One of my OKRs for the next 8 weeks is:
Objective: Learn skill paths to explore artistic interests
- Key Result 1: Write and produce 5 songs
- Key Result 2: Take biweekly Ableton lessons (music production software)
- Key Result 3: Program a virtual reality game in Unity
- Key Result 4: Write and publish 5 articles on Medium
You can see here that each key result should be measurable and quantitative. That means that at the end of 2 months, I can clearly answer “yes” or “no” to the question: Did I accomplish this key result? If not, to what degree has it been accomplished?
It is also crucial to note your personal tendencies when setting your key results. I designed my key results to address my personal tendency to obsessively focus small tasks if they fail to meet arbitrarily (read: irrationally) high standards. Therefore, I set high quantity goals, such as writing 5 songs, so I can motivate myself to finish a song even if it won’t win a Grammy. My goals optimize for quantity since my tendency is to fixate on quality.
You should set your goals to suit your personal tendencies. If you get paralyzed by anxiety when your goals are too quantitative, then make your key results process-oriented. For instance, instead of “write and produce 5 songs”, you might have “sit down and write/produce music for an hour a day”. The key result is now process-oriented while still being a measurable goal that helps you level up your musical skill tree.
Step 2 — Execute the actual day-to-day
I like to visualize that my mind is made up of two parts: one is the higher mind that knows what I should get done for long term goals, and the other is the lower-level child mind that is instinctive and primitive. The latter mind executes quickly and is very creative. However, it is emotionally driven by habits of desire and avoidance — just like a child.
The purpose of personal Objectives and Key Results is to provide clear focus so that the higher mind can manage the child mind in order to execute on long term goals.
For each key result, consider how you would execute it. What are tactics that help you stay focused and motivated? It is important to know the habits of your child mind so that you can design a daily routine that breaks down undesirable barriers. It is also important to consider that your child mind is childish. When a child makes a mistake, you don’t want to yell at her (at least, I hope not). If you want your child to learn from her mistakes, you gently redirect her to the right behavior and positively reinforce this behavior in the future.
Personally, my child mind loves eating sugar late at night and sleeping late, which makes me wake up late and groggy the next day. However, I know that I am the most productive in the mornings. This is crucial information to know because it helps me anticipate the roadblocks my child mind will create when executing on my Objectives and Key Results.
Based on my understanding of my child’s mind, I use the following four tactics.
1. Set a single main goal for the day: What’s the one thing that I can do today where, if I get it done, I’ll be happy?
This should be completable in 2.5–3 hours. An example of this might be: write an article draft about taking time off.
2. Give an uninterrupted 2.5–3 hour time block in the morning to do it. ☀️
In Angela’s Duckworth’s book Grit, she says that the key to achieving expertise in a skill is through high-quality, deliberate practice. Deliberate practice means uninterrupted, focused time working on specific tasks. This means: no texting your friend the latest cat meme, no clicking YouTube clickbait, and no scrolling through Instagram. If you catch yourself doing so, don’t beat yourself up; realize that it is your child mind getting distracted. Gently refocus your attention to the task at hand and congratulate yourself for successfully redirecting your energy.
2.5–3 hours may seem like a short period of time, but for deliberate practice it is actually quite long. This time block also doesn’t necessarily mean that you are only working 3 hours a day; it simply means that there is deliberate practice on a single skill for 3 hours a day. The mornings are dedicated to a single task and the rest of the day is used flexibly for other goals. Later, as you become a productivity god/goddess, you can try ramping your deliberate practice block to longer stretches of time.
3. Timebox my work time.
I use the Pomodoro technique, where work time is segmented into 25 minute chunks, with 3–5 minutes of break between each period. If at the end of a 25 minute period, you want to continue working, only continue if you think you can do another full 25 minute chunk. If not, then take a brief break. By scheduling short, frequent breaks, the mind is given time to recover and stay alert. I also avoid my phone and laptop during breaks to stay feeling refreshed.
11/10 would recommend.
Meditation techniques provides me greater self-awareness of my body’s stress levels. When I feel anxious and don’t have time for a full meditation, I gently focus on breath for a couple seconds and do a body scan. It isn’t a magic wand that eliminates anxiety (I’d have a billion bucks if I could do that), but it brings my attention to where I am feeling negative sensations in my body. It also reminds me that they are simply physical sensations and it’s not the end of the world.
Setting a single main goal for the day provides direction. Is the thing I’m working on now directly fulfilling my daily goal, and is the daily goal directly fulfilling a key result? If not, then gently re-orient myself.
Based on your child mind, design a daily routine that helps you fulfill your goals.
Step 3 — Stay accountable
It is incredibly helpful to have an accountability buddy to check in on progress. I chat about the status of my personal OKRs with my significant other once every few days, which keeps me on track.
If you want to go the extra mile to stay accountable, publicly declare your goals. Because of the human need to be consistent, taking a public stance will make you much more likely to follow through with your goals because humans feel bad if we say we will do something and don’t end up doing it.
Writing this article provides me with accountability since I am publicly posting my personal OKRs. I am probably more likely to follow through now that there is a (self-imposed) external pressure to do so.
And remember to self-care!
When managing your own time, you’re really doing two things at once: you’re managing and you’re also executing. This can get overwhelming at times and that is why self-care is so important.
Self-care should make you feel good in the short-term and improve your health in the long-term.
Figuring out the right self-care habits is a life-long process. Some examples:
- Go to the gym
- Play Smash Ultimate
- Dance on a night out with friends
- Take a nap
- Read a neuroscience textbook (Apparently my dad likes to do this to unwind 🤔hey, whatever works for you)
For extroverted folks, self-care could be a night out with your friends. For fellow bookworms, reading a science fiction novel could be your form of self-care. Do what works for you.
Note: Sometimes I end up feeling guilty if I don’t give myself the self-care that I told myself I would! Don’t be me. Self-care is for the purpose of nurturing yourself and your inner child. Be gentle with yourself if you don’t fulfill your self-care goals, because that is also self-care.
I hope this inspires readers to reflect, think about their personal goals, and achieve them. Formalizing the process of taking time off has been several years in the making for someone like me who has taken many gap years and enjoys goal-setting, skill-building, and behavioral design.
Stay posted for Part II, which will have the outcomes of my OKR plan.
Did this post resonate with you? Let me know your thoughts in the comments below! 👏