Every week, I write an article, and every week, I am pretty sure it will be my last. After all, I don’t have that much to say. After my sister hits the “publish” button, I give myself a day, and then I think, “Oh, crap. I have no ideas left for next week.” Then, every new week, I go through all the same emotions: despair, confusion, inspiration, then… satisfaction. A week later, I do it all over again. And again. And again.
If you had asked me when I first started this newsletter whether I thought I could write an article a week for almost three years, I would have told you no. After all, the idea of writing over 150 articles seemed ludicrous. Where would I find that kind of time? How would I even get enough ideas for that many posts? Why would anyone want to read them?
This is how the world looks when you are staring down the barrel of something that you aren’t sure you know how to do. It feels so daunting that you can’t imagine ever achieving it. The activation energy it takes to even start working toward a goal like that is so great that we often give up before taking a single step.
There’s something in your life that probably feels like that right now. It looms too large and feels too big to tackle. It is the white whale to your Captain Ahab. You have been avoiding it because you don’t know what to do or how you’ll even get started. Before you read the rest of this article, write a note for yourself about what it is. Then continue on.
Elephant eating and goal setting
Desmond Tutu once said, “There is only one way to eat an elephant: a bite at a time.” (ref) No one eats an elephant in one bite, but if you were challenged to do so, and it was a life-and-death situation, you would do it the exact same way: one bite at a time.
I have struggled with clutter my whole life. I grew up with a lot of economic uncertainty; although we were middle class, my parents often struggled to make the mortgage and openly shared some of the stress they felt around money. It always felt like this dark cloud hanging over us. As a result, I have a very complicated relationship with money. I’ve found myself having a hard time letting go of things. I never noticed this until I started dating David, and he pointed it out to me… but it’s something I’ve struggled with to this day.
I look in my closet and think, “Maybe I will wear that someday,” knowing that I probably won’t. In the back of my closet is the eBay Inventors jacket that each of us got when the first patent with our name on it was issued. I never wore it because it’s a faux leather jacket with a giant patch on it (not really my style). But it meant so much to my 27-year-old self to be given that jacket, so I held onto it for years.
Objects are imbued with meaning for me, so letting go of them is really, really hard. However, it’s also necessary sometimes. That’s why, this year, I decided to embark on something different: rather than say that I was actually going to “declutter” (with all the implications and weight behind that term), I decided to set a timer for 20 minutes a day just for cleaning and donating what I could. It was a simple way of reframing things, but it also made the task more manageable. It felt a lot less daunting to commit to making progress a little bit at a time than to stare at a lofty goal I felt like I would never achieve.
Since reframing my goal this way, I’ve given away or donated over a thousand items that I no longer need. And when we travel through the house, it is really cathartic seeing the difference in the space—cathartic enough to encourage me to keep going from that milestone to the next one, and the next one after that.
This process of unpacking the problem helped me overcome my worst impulses. Of course, it hasn’t completely solved everything; I still struggle to let go, and some days are easier than others. But now I have a way to process each task and move forward. It is a journey, not a single moment of truth, and it can only be done by breaking it down—just like eating an elephant.
Moving forward in your career when you feel stuck
The times I struggled most in my career were the times when I felt stuck. I was bored, frustrated, and uninspired by my work. Every day was a slog. At one point, after my first child was born, I took on a role in Corporate Strategy. I thought it would be a fun break from the grind of operating, especially since I had been working long hours under tremendous stress for a long time.
It was true that the stress eased up quite a bit, but soon, the opposite problem emerged. I was finishing my work in a few hours and spending the rest of the day sitting around, wondering what to do with myself. It was the easiest job I’d ever had while also being the worst. The lack of meaning and the sense that I was drifting haunted me. I had a newborn to look after, so I was not in a position to change jobs. I felt mired in place.
I debated just coasting. I was working part time, but still got full benefits and stock. I had plenty of time to spend with my new baby. On paper, it should have been ideal. After a few months, though, I realized I didn’t have the endurance to sit on the sidelines. So I had to power through. I created a new role and built out the social commerce and charity verticals. I still struggled, so I had to pick myself up and create my own momentum. I made the decision to leave tech and focus on a side company I had with my sister. But then a VP I’d resigned from working with offered to find me another job. Suddenly, a few weeks later, I was the head of the eBay buyer experience. Then, after another pregnancy and another baby, I went to Facebook.
During this six-year period of being pregnant and having three kids, I had to create my own momentum. The only way to sail in stagnant waters was to start to row. I had to jump from place to place to find where I belonged, but it helped me get through a challenging time in my career—and it taught me that slow progress is better than no progress.
Breaking the impossible down into the possible
I’ve written before about the importance of tackling tough goals one step at a time, but this is sometimes easier said than done, especially when it comes to important tasks. With that in mind, here are my top four tips for making the impossible possible.
Start from the end. It can be hard to make progress when your goals are vague, like “make an impact at work” or “publish a successful newsletter.” This is where it pays to be specific. Ask yourself, “What is it that I want to achieve?” Define what success looks like to you first and foremost, down to the details. Write it down if possible (remember what I told you at the beginning of this article?). Understanding the details of the endpoint will make getting there feel more within reach.
Define the first bite. What does the first step look like? Don’t be afraid to go as granular as you can with this. The goal is to make the first step manageable. The smaller and easier it is to tackle, the more momentum you’ll have to do it again, rather than getting discouraged. Think about the smallest reasonable action you can take, and start there.
Break down the elephant. Now that you’ve figured out the first bite, what do the second to 999th bites look like? Do they get bigger, or stay the same size? How do you mark time and progress? Measuring these things is important for staying on track and preventing the goal from slipping back into “insurmountable” territory.
Celebrate the milestones. When it looks like an infinite path, the road feels much more daunting. Having clear milestones is key. By celebrating each step you take, you’re not only giving yourself the motivation to keep going, but you’re also reminding yourself of all the progress you’ve made, which can be tricky to spot when you’re in the middle of a long journey. When you’re staring down the barrel of spending years and years doing something, it feels like too much. But imagine spending those years not doing it. Did the same amount of time pass or not?
I avoided working out for years and years and years, despite constant nagging from my very athletic sister. I have an inherited physical condition, which one of my kids also has, that makes it difficult for me to sweat to release heat. Working out would often mean overheating and the potential to pass out, which happened more than once. For years I avoided physical activity like the plague.
Then I realized that I wasn’t going to be young forever, and with the birth of my third child, who had colic, I was forced into a lifestyle change. She wouldn’t go to sleep because she was so unhappy every evening, and the only way to get her to go to bed was to get on the exercise machine, turn off all the lights, and work out to create white noise for her. And it worked. Thanks to her, I have worked out almost every day for 11 years, and now exercise is an integral part of my life.
Now that I’m in my forties, though, I realize that I’m losing muscle mass, and my avoidance of strength training is catching up with me. I’m on to the next elephant. Rather than avoiding this, I decided to go through. I found a workout buddy, and we’re holding each other accountable for making progress on strength training. Instead of looking at the challenge ahead and staying paralyzed, we’re breaking it down, one workout at a time, and seeing progress in real time. This gives us the motivation to keep pushing forward.
“The best way out is always through,” a quote attributed to the poet Robert Frost, holds wisdom even to this day. When you’re facing a challenge that seems insurmountable, it can be easy to get stuck in a holding pattern. But even the most insurmountable task can be accomplished by taking it one step at a time. By breaking the journey down into bite-sized pieces, I’ve been able to make lasting changes to my career, my house, and my health—and publish in this Substack for 137 weeks and counting.
Look back on that goal you wrote down at the beginning of this article. Consider how you can break it down into challenges you can manage, and then ask yourself: what else could you accomplish by taking it one step at a time?
How Robert Frost’s words resonate stillRead MorePerspectives
