5 Ways To Measure Your Own Progress

Bethany Crystal
May 31 · 6 min read

One of the trickiest parts about being an adult is how difficult it can be to measure your own progress. Sometimes it’s hard to tell whether you’re moving forward, standing still, or (worse yet) going backwards.

Back in school, progress works something like this:

Teacher: “Okay, now we’re going to learn…algebra!”

You: 😱”But…that sounds so scary! I’ll never learn!”

Teacher: “Don’t worry! We’ll work together step by step.”

— — One Month Later — -

You: “The struggle is real! I don’t get it!”

Teacher: “Just study like this instead. Practice every day. You’ll be ready for the big exam.”

— — Two Months Later — -

You: “Wow! I passed my algebra test! I guess I learned algebra now! I can do anything. I AM UNSTOPPABLE. WORLD — COME AT ME.”

Teacher: “Great job! I knew you could do it. Now — it’s time to learn…geometry!”

You: 😱

::process repeats::

But in the real world, there are no lesson plans or clear guidelines. You don’t know if you’re in an algebra class, a geometry class, an English class, or on summer break. From the day you leave a classroom for the very last time, everything else becomes independent study. For life. Good luck.

I’m the kind of person who doesn’t like standing still. Never have, never will. So I’m constantly thinking about where I am today, where I want to be tomorrow, and how I can measure that in micro-increments to keep myself motivated.

Here are 5 ways I measure progress in myself.


1. Set mini goals and benchmarks.

Practice makes permanent. I know the best way to learn something new is to just do it all the time. That’s why the easiest way I like to measure my own progress is to set “mini goals” for myself, then look for ways to practice them. For instance, I might set this as a goal for myself: “I want to get better at extemporaneous speeches.”

In that case, each week, I would look around and ask, “What can I do this week to get better at that goal?” I might notice that on Tuesday, I am kicking off an event at work, so maybe I’ll decide to use that as an opportunity to practice speaking on the fly. I might also notice that my husband and I are hosting people at our apartment on Saturday, so maybe I’ll commit myself to giving an impromptu toast / welcome at some point in the evening. That’s already two chances in a single week to get more exposure to the thing I want to get better at doing.

While it’s unlikely that you’ll see noticeable progress in yourself on a week to week basis, focus on the thing you can control — giving yourself exposure to it. From there on out, you can pay attention to other things that come next.


2. Do the same thing over and over. Look for micro-improvements.

One of my favorite videos of progress is watching this skateboarding Christian Flores tell the story of how he attempted the same trick 2,000 times before nailing it.

What’s interesting is — even with no prior understanding of skateboarding, you can tell he’s getting a little bit better when his feet start to land on the board before he falls as opposed to missing it completely. That said, you can only get that granular in seeing your own progress if you do something enough times to find patterns. So look for an activity to repeat enough times to measure this in yourself.

As a personal example, last year I went on a blogging spree where I committed to publishing something every day for four months. While it was actually pretty hard for me to answer the question, “Am I a better writer?” at the end of that, one of the biggest tells for me was when I came back to something I had written a year before. And it sucked. To me, that was a sign of progress. My first drafts are better than they used to be. For now, I’ll take it.


3. Keep an eye out for third-party observers.

It’s always easier to watch someone else and gauge their process than to observe it in yourself. If I’m lucky, sometimes a third-party observer will share indications of progress with me. But this doesn’t happen nearly as often as I wish it would, and it’s rarely as direct as I would prefer. That said, here are a few examples of ways I’ve noticed people share this with me:

  • Direct: “Wow. That presentation really blew me away. You’ve come a long way since last year.”
  • Indirect: “Here’s an article I found that reminded me of one of the questions you asked in your presentation from the other day.”
  • Observational: “I noticed you’ve been doing [insert action or behavior] a lot more lately.”

As with any piece of feedback, I try to treat it as a single input. But I do use these examples as indications of what things people around me pick up about my day-to-day habits. Whether I agree or not is a separate matter.

Pro Tip: It’s incredibly rare to receive “direct” observational progress as shown in the first example. If you come across someone who actively shares an observation about your progress with you like that, you should keep them around. And if you’re looking for people who might help you in this way, try finding people you see only every few months or a couple of times a year. They’ll be the most likely to pick up on changes from one interaction to the next.


4. Pay attention to introductions.

A question I sometimes ask myself is, “How would my colleagues or friends describe me in a reference to someone else?”

Of course, it’s impossible to answer this question in a vacuum. Instead I try to pay attention to whatever subtle clues cross my path. Sometimes, I’ll get mini-indications of this in the way that people introduce me to colleagues in email or in networking situations. For example, there’s a big difference between these two intros:

  • “This is Bethany. We work together.”
  • “This is Bethany. She runs our portfolio network.”

One may imply a sense of collaboration, teamwork, and camaraderie. The second tends more toward a sense of ownership, trust, and autonomy. While there’s no “correct” answer, understanding how different people introduce me can offer tiny clues of how I’m perceived more broadly.

Pro Tip: If you find a lot of inconsistency in how people introduce you, maybe this means you need to crystallize your job or personal brand better. If you notice people inserting flattering adjectives in their introductions, take that as a very big compliment. And if you don’t like something about the way you’re introduced, ask yourself, “What behavior can I change to adjust this person’s perception of me?” Then go try that thing. Then listen again the next time and see if anything has changed.

If you’re feeling bold, you can ask this question directly: “What would you say about me in a reference to someone else?” While it’s likely that people will only tell you nice things to your face, the trick with this is to listen to what they aren’t saying, then decide if there’s a growth area in there for you to work on.


5. Clock any invitations to events.

As another correlative indication of progress, I pay attention to the types of things I’m invited to attend from others. This is perhaps one of the easiest ways to get a sense of how you’re perceived — and whether you are making progress toward that goal. When I first joined USV, I used to get a LOT of email inbound traffic from people inviting me to speak at blockchain events or invest in their crypto-currencies. While I do find this space interesting, it’s certainly not where I spend 90% of my headspace. And to me, that was a clear indication that I wasn’t being external enough about my role, my job, or my place in the firm. Today, I am starting to get more inbound that’s much more directionally related to communities, networks, organizational dynamics, and leadership. To me, that is progress.

I like to pay attention to this personally and socially as well. For instance, over the past four years, I’ve been getting more involved with the NYC educational community. I co-founded a summer initiative that helps CUNY students learn professional skills that will help them in their careers. I’m on the board of a computer science charter school in the Bronx, and I attend meetups and initiatives with educators in the city. A couple of weeks ago, someone in this space invited me to an education-related fundraising event in the city. I saw this as a huge win for my personal and professional brand. To me, that showed, “Someone else is validating my interest in this thing enough to invite me to join them at an event.”


rogress isn’t perfect. It’s painful, incremental, and it’s rarely linear.

But often the hardest part is being able to pay attention to where you’re at, and that’s the part I’m trying to demystify a bit. These tips and behaviors really help me anchor myself in where I am today and where I’m trying to get tomorrow. Hopefully they’ll help you, too.


Originally published at Dry Erase.

Bethany Crystal

Written by

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC