Milestones. They artfully mark the progression of our lives to a higher, better place. They don’t come around that often and usually, they take a lot of hard work. But they are always, always worth their title. 

My milestones all have one thing in common: fear. Not bad fear — good fear…the kind you conquer. The kind that will hold you back if you let it. But you don’t let it — you use it as a stepping stone and stand on top of that next milestone. 

Not every milestone sounds glorious and grand — some sound silly but represent something much greater within yourself. Here are a few of mine: 

  • Milestone #1: Student Teaching 
  • Milestone #2: Conquering Public Transportation
  • Milestone #3: Taking a Job on Capitol Hill
  • Milestone #4: Skydiving
  • Milestone #5: Speaking on live, national television
  • Milestone #6: Overcoming an Obsession with Thinness
  • Milestone #7: Realizing I’m Weird Just Like Everyone Else

Now, these are all very different but they all come with their own set of overcome fears and anxieties. For example, taking public transportation (#2) when I moved to DC as an intern was literally one of the most terrifying things to me. I just knew I’d get lost and confused. I thought I would look stupid and never get anywhere. But I had to just do it and believe I was smart enough to get it. And I did. 

Living & working in Washington, DC

Somewhere along the way, I stopped caring about being skinny (#6). I mean, I care about maintaining a healthy weight and like to be attractive but that former obsession with crop topped VS models, skinny little arms and tummies with no love handles? Gone. Don’t want to be that, don’t need to be that. When I overcame that, you better BELIEVE it was a milestone moment! 

I used to think I was the only who sucked at and hated small talk. I used to think I was the only one who made awkward comments in the elevator or totally ungracefully left conversations at cocktail parties. I thought I was the only one who hadn’t been kissed when I was 16, and the only one who was really bad at second dates. Eventually I realized that everyone has their weird stuff (#7). And a lot of it’s the same weird stuff as other people.

Milestone #1 probably sounds a bit silly, right? Why is this such a big deal? For me, it was. I was inexplicably terrified at the thought of being responsible for a classroom. I nearly quit the education program over it. I would have rather done anything but that. I remember walking through Target in tears over it when my Dad gave me a serious pep talk and convinced me to do it. It ended up not being that hard — and taught me a lesson to do things you are scared of — you are stronger than you think you are! 

Public speaking is something I do often & all these things gave me more confidence

Skydiving (#4) was super scary to me. The last thing your body wants to do is hurl itself out of a plane. But it literally felt like conquering ALL of my fears at one time. It was terrifying and empowering at the same time. It made for literally one of the best weekends of my life. It represented much more than just the act of skydiving itself. 

If you told me when I was in college that I would work for Congress on Capitol Hill (#3) in Washington, DC — I would have laughed in your face. That sounded like something people who graduated from Harvard did to me. Something people with more ambition than me, that’s for sure. But life comes together and you do hard things. Moving to DC and eventually taking a job on Capitol Hill was like going in blind. I had no idea how this was going to turn out but I was doing it. It could backfire, I said. I could end up being terrible. Of course, it was one of the best decisions I ever made. 

I’m weird, just like everyone else 🙂

Appearing live on national television (#5) to debate politics on MSNBC & Fox News was it’s own kind of scary. It was so scary, in fact, that after doing it three times, I stopped doing it. It was not for me. Just not my thing. But I did it even when I was freaking out. And guess what? It served me well to TRY something like that. If I got the chance again these days, I’d do it again. 

How do you find these milestone moments in your own life? You find those very things you are scared of and figure out a way to say YES. This can be as small as introducing yourself to someone important but intimidating in your field of work. It could be committing to writing the book you’ve always thought about — or signing up for the marathon you are afraid you won’t be able to run. Make a list of the things you are afraid of. Then decide how you can conquer those fears — and I guaruntee you milestone moments will appear with every one. 

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