20 Lessons From My Twenties

As I say goodbye to my twenties and hello to an exciting new decade, I can’t help but think back on the incredible life lessons the past ten years have brought with them. Your twenties are an incredibly transformative decade and a period of life where you learn a lot about yourself: what drives and inspires you, what you value in a partner, what you personally prioritize, and those lessons give better shape to pinpointing what you want in life on a broader scale.

While I feel like I’ll be learning some of these lessons for the rest of time, here are some of my key takeaways and 20 lessons from my twenties:

The Importance of Life Experiences vs. Things

1. This mentality is partly the product of being a millennial and partly due to island mentality and a love of travel that was fostered in my early twenties. The value of experiences has long trumped the value of the tangible for me, and that approach to life continues to guide us when it comes to prioritizing spending. I’d rather have a life of great travels and substantial memories than a large house, a new car or designer handbags. I realize that for some people this isn’t an either/or scenario but for many it is a very real give and take. After working in hospitality for 3+ years and interacting with guests from a variety of backgrounds, there’s one thing that comes through from our older, wiser guests: for nearly everyone, it wasn’t the things that made life great, it was the memories and the shared experiences with loved ones. I’ve not talked with one person who looks back on life and mentioned regret over not buying things; every missed opportunity had to do with the experiential.

Quality of Friendships

2. When people talk about quality over quantity, friendship represents this contrast the most fervently. I’ve gained lifelong friends throughout this past decade and said goodbye to some close friends that I had earlier on in my twenties. One of the most important things I’ve learned from this is that parting ways with friends doesn’t show weakness or failure; there are some friendships that are incredibly valuable and life-changing during certain periods of life, but some friendships do get outgrown and that’s okay. Cultivating high quality friendships for a lifelong support system is key, and this decade has brought many standout relationships my way.

Your Parents Know a Thing or Two

3. During my quarter-life crisis and woe-is-me moments, my parents continued to assure me that life would work out, and – dare I admit?! – they were right. When my 25th birthday was approaching, I found myself deeply concerned about my future, different prospects, my career path, etc. During many conversations with my dad (ever the optimist), he assured me that things would come together; that they always did. While I tend to disagree with that mentality, I think there’s some truth to this. Things work out – maybe not quite how you planned – but they work out for those that work hard, stay optimistic, stay dedicated and continue to be their best self. A strong work ethic and a positive outlook do get noticed, and while opportunities may not manifest themselves in the way we’d envisioned initially, life has a way of creating a path for us.

Take Risks

4. Your twenties are a decade to take some risks and step out of your comfort zone. When my sister and I began talking about her potential move to South Korea to teach English, she found herself a bit conflicted, as many would. What if she hated it? What if the job wasn’t a good fit? What if she could have taken this year to go into the workforce into a more traditional job? What if, what if, what if? After my first international move to London, my perspective on life-altering experiences like this made me a complete ambassador for these kinds of opportunities/’risks’. The reality is that what seemed like a risk really wasn’t that much of a risk at all. That is to say, what’s the worst case scenario for most of us? What if you spend a year abroad, test out a new career path, or decide to move to a new destination and don’t like it? Well, then you tried, and the experience is not for nothing. Even a terrible experience is a learning experience. The risks we take and opportunities we test out teach us what we like, what we don’t, what we value in life, etc. Most of us are fortunate to have an emotional support system in family and friends that will be there to lift us up and help us out of situations that don’t work out.

The Importance of Relationships

5. Relationships are the most important thing in life. Full stop.

I’m not referring exclusively to romantic relationships, but the entire spectrum of relationships: relationships with parents, siblings, significant other, friends, co-workers, etc. I recently watched a great TedTalk by Robert Waldinger on the topic of what makes a great life. After years of study (one of the most expansive longitudinal studies ever done), researchers discovered that true happiness at the end of life hinged on one main thing throughout a person’s lifetime: strong relationships.

This is something I struggle with and I don’t think I’m alone in this: keeping and fostering strong relationships takes work, and it’s something I’ve taken more seriously during the latter part of my twenties and something that I find of utmost importance as I enter this next decade. That means taking the time to call friends and get an update, to write and send a card for a special occasion, to shoot an email to check in on a friend’s new job, and to carve out time to Skype with family overseas. It takes time and effort from everyone involved, and it’s easy to drop the ball when the effort isn’t reciprocated (I fall victim to this frequently). A focus on keeping and strengthening existing relationships is something that I admire hugely in my husband’s approach to life and friendships – it’s a way that he constantly inspires me to do the same with my own friends and family.

Life Isn’t Always Easy

6. But we knew that, right? Of course life isn’t always easy, but the hardest thing is that the right choices aren’t always easy and as you grow you’re faced with more of those realities. There are inherent challenges with learning, moving and growing, and it’s all part of the process. We’re faced with a host of circumstances that can be difficult to navigate whether it’s choosing between career and relationship, or leaving behind friends, family and a comfort zone to pursue an opportunity abroad. Growth can be painful (our personal trainer reminds us of this all the time!). I faced this when moving to Anguilla and have to remind myself that I’m human, which means I deserve a bit of time to acclimate and adjust to new realities.

Prioritizing Family Time is Critical

7. I have always been fortunate in that I have a strong family unit and close bonds with my parents, grandparents, sister and even cousins. As with friendship though, staying close with family means prioritizing that time together (this relates to relationships being of the utmost importance). For many of us that move away from home – some of us internationally – having in-person family time can be difficult. Scott and I have made a conscious effort to always focus on our families: phone calls, Skype sessions (even my grandmother is on Skype!), and bonding experiences at least once per year. My family joined us for our week in Guatemala earlier this year, and we’ve enjoyed multiple international experiences with Scott’s family. Those trips could have easily been done solo or with friends, but our families are incredibly important to us, and focusing on that time with them makes our lives richer. It’s easy to allow weeks, and even months, escape without talking. Take responsibility for your relationships and focus on fostering them. Don’t let old grudges and the past bog you down (all families have history!). Focus on the good and try to make that time together really count. For those of us that have strong family bonds, remember how fortunate you are to have a family that loves and supports you.

Continue to Learn, Grow and Map Out the Future

8. There’s a fine balance to this: wanting to continue to grown, learn and achieve more while not berating yourself for not having come far enough. In the weeks approaching my 30th birthday, I struggled with this. Had I done what I set out to do? Had I accomplished enough in this past decade? Had I built up a better version of myself to present to the world? Ultimately, am I proud of the person that I am at this point in life? 

I found that I was getting down on myself, focusing only on the things that I didn’t accomplish versus also taking into consideration the things that I have accomplished. In a TedTalk by Dan Pallotta, he discusses the importance of deadlines and commitments to achieving our dreams, whatever they may be. I think it’s important for all of us to want to continue to learn and grow and better ourselves, and that means aiming higher, pushing harder and being our best self, with goals in mind. That being said – as hard as this can be – I think it’s also important to not lose sight of what we have done while striving for greater things. Taking a moment to remember how far we’ve come is encouragement to keep persevering.

Adulthood is Different Things to Different People

9. Your twenties, the latter part specifically, is a particularly transitional period into real life adulthood. We witnessed many marriages (including our own!) or the development of many significant relationships, pregnancies and babies, home ownership, career achievements, international moves, etc.

As a child, I couldn’t wait to be an adult; to have the freedom and autonomy that it brings. You know what? Adulthood is awesome. For me, it means living a great life with a man who I adore, globetrotting, and balancing working hard and living a life of happiness. One thing that is clear though is that adulthood means different things to different people. Not everyone’s take on adulthood mirrors mine. For some, adulthood is buying a house, settling down, having children. For some, it’s purely focusing on career goals. For some, it’s having he ability to lead a nomadic life or pursue entrepreneurial endeavours. All of that is great. It’s your life and that’s the beauty of being an adult and having autonomy: you can create the life that you want, and it doesn’t have the be the same as everyone else’s. Not everyone will agree with the way you choose to live your life and it’s an aha moment when you realize that’s totally okay! We all have our own goals for ourselves and it’s our obligation to create the life that we feel brings the most value and worth to our lives.

Figure Out Your Style

10. Whatever your style is, find it and be true to it. Of course there’s experimentation and the discovery phase but one of the beautiful things about having tried lots of trends (many unsuccessfully), is that you begin to realize what looks good on you, what you feel good in, and what doesn’t. I can quickly look through a site and pinpoint the handful of styles that will complement my figure, and I know which colors will work best. Especially now, when returning an order isn’t really an option, I have a great idea of which clothing and shoes I will actually wear, what sizes work best, and which styles are absolute no-nos for me, regardless of how great they look on the 5′ 11″ fashion blogger. It’s about feeling good in your skin, and knowing what you feel best in helps!

There will be people who want to bring you down

11. It’s easy to think that the mean girl mentality ends as you enter adulthood, but the sad reality is that there are mean girls – and boys! – in life that will be that way forever. They’ll be 40-year-old mean girls and curmudgeonly 70 year olds, and it’s important to recognize who the toxic people in life are and try to push the negativity out. Whether it’s in work, in your community, or even in your family, there will always be people who bring a negative energy to life. My biggest takeaway after interacting with those types of people? It sucks far more for them to live like that than it does for me to have to interact with them. As hard as it can be, try to overcome, focus on what’s important (easier said than done!), and know that at the end of the day their negativity is more about them than it is about you.

Focus on Healthy Habits

12. I’m happy to say that I’m a healthier person now than I was at twenty. I didn’t grow up in a household that particularly focused on health and wellness but as I came into my own, I found myself more and more interested in fitness and healthy practices. For the most part it started for superficial reasons, but those early days of cranking away in my apartment’s gym helped me become focused on the importance of being my healthiest self. For me, that means a healthy diet that doesn’t include meat, that means working out regularly including a few days with a trainer, and trying to incorporate some general activity into my day-to-day (and when traveling). It’s easy to make excuses for not working out or not eating healthy, but at the end of the day we have ourselves to own up to. I made working out a habit in my early twenties and I’ve stuck with it since then. If I hadn’t started a decade ago, I may still be putting it off. Start with healthy practices young and allow those practices to continue and evolve as life evolves.

It’s still a bit superficial for me, and I’d be lying if I said I didn’t work out in part to stay bathing suit ready (I mean, we live in Anguilla!), but it’s also important for me to live a lifestyle that I want to impart on my future children. I want a long, healthy life ahead; one free of diabetes (almost everyone in my family has it), and free of prescription meds. If the effort now means a healthy, active life in the future, I’m all for it.

Learn to Have a Conversation – and Focus on Listening

13. I listened to an incredible TedTalk by Celese Headlee that discussed how to have a meaningful conversation, and it stuck with me. Having a real conversation is arguably the most important life skill you can learn, yet many of us don’t really understand the art of dialoguing. Sadly, it moves further and further out of reach in a generation of texting, tweeting, WhatsApping and Facebooking people (hey, I’m guilty, too!). Learning how to have a genuine conversation is a goal that we should all pursue, for us and for others. After listening to her TedTalk (you should listen to it immediately), I’ve tried to implement different tenets each week when I talk with guests. I try to ask questions with the intent of knowing more about people, not just waiting for my turn to talk. It’s a skill that takes a lot of practice because, as we all know, listening is much harder than just hearing words. I’m a work in progress with this, but learning to be a great communicator early on is a skill that will serve us well throughout life.

Learn How to Order a Drink (or a Water)

14. Seriously, guys, this is a lesson that I legitimately learned in my twenties: the art of ordering a cocktail. But it goes beyond that really. It’s the art of learning how to be in different situations, and how to navigate any situation elegantly. It’s being able to look at a menu or a cocktail list, knowing what you like – and what you don’t! – and ordering with confidence. When there’s no drink list available, it’s about having a go-to that you know a bartender can likely whip up. If you sort of like wine but don’t really know what you do like, learn. At 23, I couldn’t have appreciated wine tasting in my home region of Napa or Sonoma, but now we plan trips dedicated to wine tasting experiences (e.g. our trip to La Rioia last fall and our upcoming trip to Franschhoek this fall). Learning has been so much fun and so educational. I can read a wine list with some level of confidence now, and as inconsequential as that seems, it’s one of the things I’m actually most proud about! Someone out there is reading this shaking their head, but I stand by this: skills like this may seem irrelevant, but they make you feel more confident in social situations, especially in business-related outings. If you’re not a drinker, this means having the confidence to say you’ll stick with sparkling water (or whatever your beverage of choice is) and not batting a lash.

Learn to be Financially Wise

15. I was forced to learn how to be financially responsible at a young age, and while I tensed at the thought of not having a safety net at the time, I’m grateful now for the lessons I learned early on. At 18, I understood the realities of saving money, paying bills (from college tuition to cell phone bills and insurance), filing taxes, planning financially for larger investments, etc. I didn’t have a credit card until I was 26 years old and finally felt that I was responsible enough to make regular payments and not get myself into debt (it’s easy to fall into when you have the ability to charge anything). Everyone messes up in their early 20s (seriously, everyone has a story about a stupid moment of having their electricity disconnected or having to fork over a small fortune for missed ticket payments) but the reality is that those things can stick with you for a while and affect you when you’re doing real things in life (like buying a house, eek). Having good credit and understanding which financial tools are available and how to use them is important, as ‘adult’ as it seems. Going into my 30s, the focus now is more on how to invest wisely to make our future stable.

Don’t Neglect Your Skin

16. I knew I was getting older when my skincare regimen started taking longer than my makeup. I grew up with a mom that emphasized the importance of good skincare, even as a teenager, so I had a head start on learning how to incorporate different elements into my skincare routine. It wasn’t until my mid to late-twenties that I really started focusing on skincare with a renewed vigor. I saw the impact of my wayward teenage days spent in tanning beds (ahh, the horror) and focused more and more on spending time and money on creating a good canvas. As the years have progressed, my makeup routine has waned, but I would never leave home without my arsenal of skincare products.

Twenty-somethings: START EARLY. The truth is that once the lines are there, no moisturizer is going to remove them (I still experiment and slather on creams and face masks). Take care of your precious skin early on and be proactive about anti-aging!

Confidence is Crucial

17. I think – and hope – that confidence comes with age. That was the case for me, and I genuinely hope that everyone has a solid sense of self-worth once they’ve reached their mid-twenties. Your twenties are a decade for finding your tribe (whatever kind of tribe that may be) and your stride. It’s about knowing who you are, what you know, and what you don’t know and being confident in that. Interacting with people on a regular basis and being able to have conversations with a range of individuals has boosted my confidence immensely. I’m not great at many things (in fact, I’m good at only a few things!), but I’ve become confident with the person that I am, including the shortcomings.

Don’t Impart Your Aspirations on Others

18. This ties in to a few things I’ve referenced earlier, but I think it’s something that is worth discussing on its own. This is something I constantly fight myself on, and I know I’m not alone. Particularly for those of us that are very goal-driven, it can be difficult to see family members or friends who are not that way. I want to take on more and more responsibilities, I want to see the world, I want to do [insert whatever here], and I can’t seem to comprehend why the people whom I love and respect don’t want the same! Why don’t they, too, want greatness for themselves? Why are they okay with being just okay?

Well, biggest lesson here (again, I’m still learning, but I know it’s a lesson I must learn): what I see as them just being ‘okay’, is me being a bit judgmental. There. I said it.

Just because I want to move up or expand my skill set, doesn’t mean that someone who’s comfortable in their current position is doing something wrong. Why would I criticize someone for being content and instead look at them as being complacent? It’s a perspective thing.

Just because I want to travel doesn’t mean that someone who doesn’t want to travel is small-minded. It’s a personal preference, and while I may struggle with that fact (I mean, they don’t know what they’re missing, right?!), it’s unkind of me to assume that something I want for my life is something that all people should want for their lives, too. Remember that whole thing about adulthood meaning different things to different people? Yeah. So, while I’m spending a small fortune seeing new countries, a friend or family member may choose to spend that same amount of money putting a down payment on a house. Neither one of these things is more right than the other – it’s a choice to make.

Focus on Being a Global Citizen

19. Most millennials will resonate with this idea since it’s something that has been so ingrained in many of us as we’ve grown. Global citizenship wasn’t emphasized when we were kids, but as the world as grown smaller, our needs to grow more culturally aware and globally focused has become greater. The world we live in now has us dealing with issues that impact us on a worldwide scale (climate change, poverty, gender inequalities, etc.), which means that it’s our responsibility to think more broadly and find solutions that can impact us on a global scale. It’s also our responsibility to raise a future generation that understands this early on. To me, that means raising children that are culturally sensitive, that speak multiple languages, and that realize that the world is their playing field, not just a single country.

The Importance of Happiness – The Ultimate Goal

20. I referenced this in a couple of the bullet points above, mostly related to strong relationships, but one of the most important lessons from my twenties is something that I think we all inherently understand: happiness is the ultimate goal. We all achieve that in different ways but for most of us finding a balance is key. It’s easy to get wrapped up in career goals (for some of us, that is happiness!), but finding the give-and-take is something that takes time and effort. We need to prioritize our health and mental wellness while also focusing on career objectives and life goals. I’ve found that taking time away to travel, see new destinations and gain new perspectives, makes me a better contributor. Taking time to focus on ourselves occasionally doesn’t mean that we’re neglecting other things. Sometimes focusing on ourselves makes us better equipped to deal with situations more effectively. Cheers to a life of happiness!

What major lessons did you learn in your twenties? Any tips you would give your twenty-year-old self?