To-Do or Not to Do

Reconciling structure with freedom in my sabbatical

I intentionally started my sabbatical with no checklists. I woke up everyday, and did whatever I felt like, except for any pre-scheduled health appointments. Initially, the empty calendar space felt terrifying. But over the course of a few days, that feeling transformed into freedom. One of my favorite days of the “no agenda” phase of my sabbatical was hanging out in Prospect Park, listening to Britney Spears' new memoir, indulging in 90s pop culture (a phase that I totally missed growing up across India/Saudi Arabia). 

But over time, the lack of structure got to me. I was stressed that I wasn’t making enough progress on my next steps. This stress was exacerbated by the fear of running out of money before discovering answers. Some days, I found it difficult to relax, which made me feel guilty about not “maximizing” rest during my sabbatical. Overwhelmed with my feelings, I would mindlessly scroll for hours on my phone, only to later regret all my decisions and feel even further behind. 

I was spending more time stressing out if I was doing things right than doing the thing. 

Looking back, I was fighting the fact that I am a creature of habit. I need structure to feel good about what I’m doing, but I also need permission to take a break if it’s not serving me in that moment. In many ways, I was fighting my instincts, molding my sabbatical into what I thought it “should” be instead of what I needed from it. I’d always envisioned spending my sabbatical actively experimenting with my next steps, guardrailing on my energy. 

Shifting towards structure 

So, I started thinking about what an ideal structure could look like. I thought about some of my happiest times in product and in my sabbatical, as well as what I was “feeling” like I was missing. I also took inspiration from different podcasts and books on time management. This thinking led me to three principles: 

• Clear goals, loosely held: I need clarity on what I am working towards on a long (aka quarter/year) and week-to-week timescale. However, I also needed to recognize that things change, whether it’s with what I’m working towards or the pace itself. Having some slack in the schedule and enforcement will be key. 

• Balanced intensity: I crave periods of sprinting intensely on a meaningful task, and taking rest periods to recover from the intensity. This was a surprising realization for me, but also not surprising, given how much I enjoyed building product at startups (until it stopped becoming fun). This is similar to running, which requires both active work and intentional recovery to actually make progress. 

• Playing the long game: making a career transition takes a while, especially for creative fields where jobs are dwindling and breaking in is harder than ever. While I do want to make this transition, I want to be thoughtful about it, avoiding the tunnel-vision achievement-oriented ambition trap I fell into with product. This means I need to be really intentional with the way I define success. 

Searching for freedom in the dunes of Mexico. This photo is from a still from a slo-mo video of me jumping with the board on. But more impressive this way :)

Turning Principles into Action

I then took the principles and converted them into concrete “rituals” to organize my time. Here’s how I implemented it: 

Clear goals, loosely held: 

• Holistic goal setting: Whether I’m planning goals for the quarter or week, I’m looking across all areas of my life. This year, the buckets are my writing projects, coaching business, inner work, relationships (family/friends/partnership), and wedding prep. This helps me ensure that I’m intentional about how much time I’m carving to different areas of my life holistically. 

  • I’m also setting intentions every week of how I want to achieve my goals. Most weeks, my intentions center on being present, accepting imperfection, and embracing the messiness of my emotions. Writing intentions doesn’t guarantee I’ll follow them every week, but increases the chance that over time, they’ll become easier to embrace. 

• Loose accountability: Most weeks, I don’t accomplish 100% of my goals. Instead of punishing myself, I ask myself: what happened? Was it something unexpected, or is there a process change I need to make? Especially in this phase of my life where so many changes are happening at once, I hold grace for myself and use it as an opportunity to learn. It’s led to some helpful tweaks in my process, ensuring the success of this process over a longer period of time. 

Balanced Intensity: 

• Mandatory rest: I schedule in rests, both on a day-to-day and quarter-to-quarter basis. 

  • Throughout my day, I have scheduled breaks to meditate/take walks, deep work time (since meetings drain me the fastest), and “nights off” where I don’t do any work or see people (including chores, wedding planning, or life stuff). 

  • Every quarter, I spend one day in silence, with my phone on airplane mode, to give my brain a longer break from stimulation. I also take one week completely off, usually to travel or spend time with my family. 

• Celebrate: At the end of each month, I give myself a little treat (whether a nice dinner, gift, or something else). Last time, I bought myself a lil macaroon from a coffee shop. 

Playing the long game: 

• Evaluate success over a long time horizon: when evaluating my week, I go to my calendar this week from last year to see where I was. Then, I look at where I am today. No matter how much I got done, I almost always have the same realization: I’ve made so much progress. I’ve also done this exercise on a smaller time horizon: looking at where I was last week vs this week. It helps me feel gratitude for everything I have done rather than focusing on what I haven’t done.  

• Embracing failure: I intentionally plan to fail at something every week. This helps me be realistic about my bandwidth while giving myself the permission to take rest or switch plans when needed. This is huge for balancing my energy and reconditioning my corporate mindset. 

New Sabbatical, New Routines

Getting to this level of clarity about my lifestyle took six months of active experimentation and reflection. Now, I feel pretty settled into my routine, with rituals like weekly planning and templates to evaluate the success of my week that allow me to  breeze through my weeks. 

Yet there’s still an anxiety gnawing at the back of my mind. Is this the most efficient way to do things? Am I falling into bad patterns, overextending myself? Tough weeks and whispers of burnout intensify the volume of my anxiety. 

But then I ask myself: is this better than where I was in June 2023, drowning in work, balancing my creative projects, and starting wedding planning? I think about how I’m genuinely excited to wake up in the morning and tackle my day. I recognize that Sunday Scaries haven’t happened in months. I celebrate that I can change my schedule at a whim, making time for a random lunch with a friend, without feeling guilty about the potential lost hours for work. Most importantly, I feel in control of my time, rather than feeling like time is passing me by.

In some ways, structure helped me uncover freedom in my sabbatical, because I’m no longer fighting myself on what I want to do. That’s the opposite of what I expected, as I thought freedom came from doing nothing. That’s definitely some people’s version of freedom, or maybe what’s sold to us through TikTok trends like “lazy girl jobs” and creators that sell courses on working three hours a day while making six figures. For better or for worse, my version of freedom involves balanced intensity, ownership through structure, and soft accountability. 

Turns out, my freedom wears a product manager hat.

PSA: I’m going to be trying out a new format of posts in the future, where I answer your questions about sabbaticals or any other topics I’ve written about in this post. Pop your questions in Google Doc here. I’ll pick a few to answer in my next newsletter. 

Thing of Note

Recap: This section is my way of bringing attention to a thing, person, or idea that’s meaningful/related to the mission of this newsletter. This week, I want to highlight Bravey by Alexi Pappas. 

The idea of a multihyphenate has always appealed to me as someone who has always had more interests than time. Alexi is a successful multihyphenate in action: Olympian athlete, badass filmmaker, and vulnerable writer/content creator. I originally picked up this book thinking it would help me figure out how to balance the competing demands of my creative entrepreneurial dream. But this book is so much more than about multihyphenates. It’s about taking a chance on yourself, reconciling your past with your future, mental health, difficult relationships with parents, navigating girlhood without a mother, romantic relationships and partnerships, and so much more. All in all, it’s about being brave in all areas of our lives. I was skeptical of the holistic nature of the book, but the more I read it, the more it helped me connect the dots between my dreams and history. 

Thanks for Reading!

I’m on a journey to create a blended career across the creative arts, tech, and business. This newsletter is my way of sharing my reflections, thoughts, and advice along the way. Here are some ways to support or further collaborate together. 

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