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Last week I celebrated my 29th birthday.

If you’re 21 and reading this, that probably sounds old. If you’re 55, that probably sounds young. And that’s exactly how I feel, too — definitely not old, but no longer a “young person,” either.

All in all, I’m excited to see what this last year of my 20s brings. And frankly, I doubt that I’ll be torn up about turning 30 a year from now.

Let’s be honest … for most of us, our 20s aren’t a walk in the park. I’ve been no exception to that rule.

Most of us spend our 20s being put through an emotional ringer. We spend an entire decade sloughing off our adolescence, trying to figure out what being an “adult” means, and becoming (sometimes harshly) acquainted with the “real world” … all while wondering who to love, what we want to do with our lives, and how to make a difference.

Not to mention there are a lot of boxes that we feel we “should” be checking by a certain age: marriage, kids, salary, job title, house, car, 401K, etc.

We may not be expected to have all of these things by the end of our 20s, but there’s a tacit expectation that we should be actively in pursuit of all of them.

And it’s hard not to think about how many (or few) boxes you’ve checked when you can so clearly look around and notice how many (more) boxes other people have checked.

Comparing yourself to other people’s “progress” in life is a risky business, and it’s one that usually leads to disappointment and self-criticism.

I’m not immune to comparison, and I can’t help but notice that there are plenty of things I haven’t achieved at 29 that I could have sworn I would have by now, if you’d asked me ten (or even five) years ago.

To be blunt, I thought I’d be further in life by now in some ways. And lately, I’ve been grappling with the difficulty of measuring my progress, given that there are many boxes I haven’t checked yet.


When I was 19, I would have guaranteed you that I’d be married by 24, and certainly have a kid or two by 29.

Of course, when I turned 24 I moved the goalpost another five years. Certainly by the time I turned 29 I would be married and maybe even have one kid.

I feel bad for the 24-year-old me because I have to reality check her by saying that present-day me is not married, doesn’t have kids, and at this rate … I will be in my 30s before either of those boxes is checked.

To be clear — I’m not exactly disappointed by this. It’s not where I expected to be, but I can see the value of not having reached those milestones in my 20s.

I think by the time those things do roll around, I will have spent a LOT of time maturing, evolving, and generally becoming prepared. And on the whole, I think that’s going to pay dividends over the course of my life.

But still … it’s hard not to compare myself to others. Heck, by the time my mom was 29, she’d been married for 7 years and was done having children. And there are plenty of Millennials who can say the same. But more on that in a second.

Other boxes I haven’t checked include:

Again, the boxes I haven’t checked don’t bother me (most days) because I realize that I made a choice to leave them unchecked.

I quit my job and started my own business. There’s a lot of risk and instability in that, and for a long time any extra resources you have either go back into the business or into your savings (because you never know what’s going to happen).

I chose freedom and autonomy over having a lot of things that other people have by 29, and I’m OK with that.

So, here’s the ultimate question I’ve been pondering lately:

How do I measure my progress when I can’t use external things (like a spouse, kids, bank account, or house) as my metric?


What I know to be true is that even though my external reality hasn’t changed as much as I would have thought by now, my internal reality has changed a LOT.

I feel like a very different person at 29 than I did at 24, and I hardly recognize who I was at 19. The progress I’ve made as a person far outweighs anything I could have attained in the material world.

But how do you measure that kind of progress when it’s so intangible?

Here are 5 big questions I’ve been asking myself, that you can ask yourself, too:

How much happier are you now? I used to be such an anxious, stressed-out control freak that for years I literally could not take a deep breath. Any therapist (had I been seeing one) would have likely prescribed me anti-anxiety meds. I’ve reached a point where now it’s weird if I’m ever that panicked. I’ve learned to relax and trust life to sort itself out, and that is a HUGE achievement for me.

How much healthier are you? For about 20 years of my life, I suffered from a chronic (not debilitating, but very frustrating and energy-draining) illness that doctors told me I would just have to “deal with” forever. In the past year, I’ve completely healed myself ONLY by changing my diet. I NEVER thought that would happen. I poured a lot of time, energy, and money into healing myself. It’s not a shiny new car that people can see, but it means infinitely more to me.

How are your relationships? There have been times in my life where I felt pretty lonely, like I didn’t have many people who really understood me or valued me for who I am. Today, that couldn’t be further from the truth. I have an incredibly solid, supportive group of friends and family who like me for exactly who I am, and who I can always be vulnerable with. Sometimes I forget how much of a luxury it is to be able to be yourself 24/7.

How much wiser are you? At 19, I thought I knew everything. At 29, I realize how little I actually know in the grand scheme of things. I’m far less convinced that I’m “right” these days, and way more open-minded to other peoples’ perspectives. I think long-term rather than short-term, and I’m learning the wisdom of letting life give me what I need, rather than what I think I want.

How much do you like yourself? If you’d asked me 5 or 10 years ago, I’m sure I wouldn’t have said that I disliked myself. But often the way you treat yourself, and the thoughts you have about yourself, unconsciously reveals the truth. I used to call myself names and be incredibly hard on myself. These days, I like who I am and I’ve found a good deal of self-acceptance. That doesn’t mean I don’t have room for improvement; it just means I have a lot more compassion and patience with myself than I used to, and I appreciate what’s great about me.

I’m sure I could come up with many more questions, but I’ll leave it at that. If you can answer these questions and realize how much has changed in the past year, two years, five years, ten years … then you’re making great progress.

If you can’t say you’ve made internal progress, that’s OK, too. It’s just shining a spotlight on a place you can choose to grow.

And hey, making external progress is also great! I fully intend to check a lot of the more “traditional” boxes in the next few years. But I think the external attainment matters less if we haven’t focused on the internal stuff, first.

So, what about you? Have you struggled with comparing yourself to other people’s progress? How have you progressed internally, instead of externally? Share with me in the comments!


What to do when you feel like you’re behind in life

Why I love jealousy (and you should, too)

Why you need to stop fighting your life and just go with it

Much Love,

Rachel (& Kristen)


This month marks our second annual Summer Freedom Series — one month of surprise bonuses meant to inspire, uplift, and make you feel free.

Two weeks ago we announced that we would be releasing a new (and FREE) e-book every week for four weeks (on Thursdays in August).

If you missed the original announcement, you can read that and download the first e-book in the series here:

What is the POINT: A jolt of hope and practical advice for anyone going through an existential crisis

This one is for you if you’re going through a period of doubt, confusion, or existential crisis and need someone to sit you down and help you figure out what to do next.


And if you missed the second e-book in the series, which we released last week, don’t forget to download that, too!

What am I meant to do with my life? (Almost) everything we know about finding your passion and having a fulfilling career

You’re definitely going to want to read this one if you’ve been struggling with how to find your purpose.

finding your passion

9 comments | add a comment | Share this > Tweet this > Email this >
  1. Reading this felt like reading myself in 8 years from now perhaps. I’m 21. This was like meditating. I always feel good about myself and relaxed. However, there are things you don’t know about yourself or just don’t want to believe them. This few minutes make me feel more healthy and prepared. Thanks, Rachel. I love your name.

  2. This is exactly what I needed to hear today. You know I’ve struggled with not having checked some of these boxes on the same timeline as my friends… but when I truly look at my relationships/happiness/etc, I can actually appreciate and be grateful for where I am. Thanks for sharing this!

    1. I’m so glad to hear that this landed in your lap at the right time! It’s so easy to get caught up in being sad or frustrated about where we haven’t gone, and every once in a while it’s good to be reminded of what matters most. 😉

  3. Those 5 questions are a great framework for something I’ve been struggling to put into words myself! I had an epiphany sometime last year (a little after I found out my Passion Profile was Thriver, actually) where I realized that for me, making my passion (writing) into my career would actually drain it of what I loved about it. What I want is pretty much the opposite of any job marketed towards Millennials…and I’m okay with that, but it confuses the heck out of a lot of other people. They also think that with an English degree I must want to move to New York and work in publishing. But I like focusing on my happiness, health, and relationships much better. Thanks for a good post!

    1. Hey Grace! So glad this was helpful to you. And I laughed at your description of getting an English major and then everyone telling you that you should move to NYC and work in publishing, because it’s so true! That’s the only thing people think English majors should do, or can do. I’m glad you’ve realized that you don’t have to follow the crowd and can incorporate your passion into your life in other ways!

  4. I’ll be 24 in a little less than 2 weeks and I’ve been trying to be at peace with where I am right now. I thought I would have done more things by now but, like you said, I am definitely in a better mindset. I love my friends and family, and I feel positive about the future. Plus, although I am still a very anxious person, I’ve learned to relax more and do more of what makes me happy and keeps me sane. Thank you for another amazing (and creepily on point) post!

    1. I love being creepily on point! 😉

      It sounds like you’ve achieved a lot of what matters, especially at such a young age! Having the right mindset is a box thats some people two or even three times your age never manage to check.

  5. Thanks for this. I am almost 42. There are heaps of things I haven’t achieved – heaps! I live in an area that seems to attract type A-personality types/go-getters. They renovate their houses and take their kids on amazing trips around the world. I have chosen a different path due to circumstances so it can be hard to be in this company. I know I have grown A LOT on the inside but it’s hard when others around you don’t understand or value that or even make derisive comments about your choices. You have to stay strong in yourself and know you have made the right decisions for you at this time. It can feel like you’re standing in a full blown gale on your own …

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