Hindsight 20/20


First of all, can I just say that the term Hindsight 20/20 seems to have a different meaning now considering the year 2020? Maybe it’s just the collective PTSD around the year no one wants to speak about but just feels like we maybe need to rethink the term now that we have a year that was such a disaster. Anyway, one benefit of getting older is our ability to look back with more clarity than ever possible when we were in the moment. As I was on reddit, I saw a great conversation around this topic where someone asked, “What’s something you wish you had done in your 20s but didn’t?”

Some answers were expected, like traveling more, getting my masters, taking a gap year, becoming financially literate. Some were more personal like not making decisions based on what my mom wants, not judging myself for having sex or not marrying the love of my life and moving to a new city to have it fall apart – ouch! Clearly some regret coming out in those answers. But it got me thinking – how would I answer this question? What would I have done then knowing what I know now?

First, I wish I wasn’t in such a rush to “grow up”. In my 20s I kept looking ahead. Kept trying to get to the next step and not fully enjoying where I was at the moment. I prioritized graduating college in 4 years rather than doing a study abroad semester. I always wanted to live abroad and really should’ve taken advantage of that program when I had the chance. I remember I looked into it but it would be additional funds from my tuition and I didn’t want to ask my parents for it. To be honest, they probably would have paid for it, but I didn’t even ask. Which is somewhat shocking as I am not really known for my shyness! I also went straight into the workforce instead of taking any time off in between to just enjoy being 21. Granted to some extent I’m reaping the benefits of that choice now, but looking back, I would have prioritized even six months to go travel or stay in a hostel and backpack just a bit before starting work which would then be my life for the rest of my life – or retirement.

Because once you get on that work hamster wheel, it’s hard to get off. You then have to always consider if taking any time off would have a negative impact on where you are currently at in your career path. Especcially advertising. Things change so rapidly in this space. It seems like even taking a couple weeks off and you come back to new news, new platforms, new data privacy rules and all that. Imagine taking a year now? It gives me anxiety to think about taking 3 months off for maternity leave at some point – like I’m going to completely forget how to do my job. I wish I would have taken some time for myself and traveled more before I locked into a job.

Or I wish I would have taken the time to get my masters. I always loved school, and I was naturally good at it. Good at testing, good at retaining info. I was lucky like that. But once I was done, I was so happy to be done, I didn’t even consider a masters. But now, while sometimes I think it would be great – the idea of going back to studying and finals would be really hard to get back into. And going back to my previous point – it would be damn near impossible to do on top of my job. I have seen people take a break to go get a masters and then return to the workforce as an option. But to be honest – and maybe this is the Millennial in me – the thought of losing a paycheck for two years while I take on a substantial amount of debt gives me more anxiety than I think the degree is worth. I think that goes back to the idea that we all grew up with – get a steady, good paying job and then keep it. Get that paycheck. Wow, what a different mentality than some of our younger cohorts right now right? We were all about get the paycheck as the number one goal. Now it seems like that’s not the top priority and I can’t say I’m mad at it.

Travel is definitely something I wish I did more of in my 20s. I’ve never stayed in a hostel. Never. I’ve never couch surfed my way through. And at this point in my life, I’m too bougie to do so. Like I’m not even trying to stay in less than a 4 star hotel at this point in my life, but back then – I would have hit up the hostel or motel6 and would have been just fine exploring. I do wish I would have prioritized travel more in my 20s. Especcially now knowing how much I love to travel. It’s literally my favorite thing. If I won the lottery and didn’t have to work anymore, I would just travel. I want to see every corner of the earth. I want to try all types of food, experience every culture I can and spend enough time in each place to really get a sense of it all – not just the highlights. It seems impossible to see everything I want to see in my lifetime so I wish I would have given myself a decade more to get a jump start.

Instead, I didn’t really start traveling until I was 30 when Christian and I started dating. Thankfully, we share that wanderlust and passion for exploring. It’s one of the first conversations we had when we met and we’ve been all over the world together. It’s also probably been the hardest part about the last two years, I feel like I’ve wasted two good years of potential travel because of COVID. We went to Morocco in January 2020 and Hawaii in July 2021. That’s it and it’s not enough. I’m dying to get back into it. If I could go back, I would have set aside even just a little bit so I could explore more. Even if it was by myself. That was another thing that held me back. When I was in my 20s I was independent, but very much also believed that traveling wasn’t something I could do by myself. I didn’t believe it was safe for me to do alone and didn’t trust in my own abilities to be able to get myself out of situations -which really wasn’t giving myself enough credit. I mean, I got myself out of a lot of situations at home and I am a natural problem solver – I would have been just fine. But I didn’t have the self-confidence in my 20s I do now.

Which brings me to the next point – I wish I would have been more self-confident and had more self-love in my 20s. I wasted so much time caring about what other people thought, trying to impress others, being hard on myself – I look back now and wish I would have just chilled out and believed in myself more. It wasn’t until recently I started to give myself a break. All growing up, my mantra was “no one is harder on me than me” but as I’ve gotten older and realized that actually people can be really hard and unforgiving – it made me realize that if I can’t give myself a break, why would I expect anyone else to?

One of the benefits of getting older is that we grow, learn and evolve – well, some of us. This growth gives us the gift of Hindsight 20/20. But I want to be clear, having hindsight into what we would have done differently doesn’t have to mean having regrets. And I would encourage you not to look at it that way. There’s no way you would have had the knowledge you have now back then to make different decisions. Also, if you’re like me – if someone would have given you the advice, you would have ignored it anyway. So don’t think about it as regret and instead use it as reasons to appreciate where you are now. Having Hindsight means you have grown and learned enough to facilitate that benefit of life. You understand more now and therefore can look back with different perspective. Hopefully it also means you can look forward and make different decisions now so in another 20-30 years, when you’re asked this question about your 30’s and 40’s, you have less you would change. Because at the end of the day – we all make mistakes. Everyone can look back and live-in what if’s and should’ve and could’ve – yes, everyone. But not all of us can honestly say we’re willing to look at ourselves now and have the courage to prioritize what makes us happy. So no matter how you answer the question “What’s something you wish you had done in your 20s but didn’t?”, before you start to dwell in the past – maybe you should be asking yourself “What’s something you want to do in the next 10 years?”. And then make a plan to do it. Thanks so much to everyone for listening. Please leave a review and share with others! You can sign up for the written version on my blog myalmostmidlifecrisis.com and follow me on Instagram, Facebook and TikTok. Until next time!




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