In the year leading up to my 30th birthday I posed the following question to just about every about-to-be-30-something I know, what do you wish you’d known at the start of your 20s that you know now?
The responses were all familiar – don’t give up, follow your heart, don’t be afraid of failure, etc.
Being the true ENTP I am, I countered, there’s no way you hadn’t heard those things when you were in your early 20s.
I mean, did anyone sit through a graduation speech or make it a single day on Facebook without being beat over the head with those life advice clichés?
Perhaps it’s the difference between hearing something and knowing it – one of the many significant distinctions I’ve come to realize in my 20s, along with these top 30 lessons learned in my last decade…
1. Everyone has something to offer.
To say I come from a competitive family would be a gross understatement. My older brother would taunt me weekly saying, name one thing you’re better than me at, other than gymnastics.
Unfortunately, this habit of comparison wasn’t particularly helpful in the real world.
Not only did I spend my early adulthood humbled daily by the remarkable talent in my surroundings, every time I met someone new, I saw how much I stood to learn from them – no matter what country they came from, what level of education they had or what lifestyle they lead.
Shifting my mindset to recognize all I could learn from others as opposed to worrying about how to best them proved far more satisfying.
2. Growth is rarely linear.
Given the economic clusterf**k of the last eight years, I often wonder if children are still being raised to believe that life, success and growth are linear.
I think we can agree that the traditional narrative of do well in school, get into a good college and get a good job is a far from a sufficient recipe for success.
It also promises a kind of order to growth that is notably absent from the roller coaster of reality.
Anticipating and embracing the nonlinearity of growth makes it far easier to push through backslides and to not be so easily deterred by setbacks.
3. Money matters.
I know all the viral headlines read I quit my six figure job to go broke traveling the world or some incarnation thereof, but having taken that trajectory in reverse I can say that what those articles fail to celebrate and recognize is right there in the headline – the freedom to travel around the world or go scoop ice cream on a small Mediterranean island or live entirely on your own terms is enabled by that six figure salary, that funded 401k, that stocked emergency fund.
A strong financial foundation enables the kind of radical freedom that allows you to leap with confidence.
So the real takeaway isn’t that money doesn’t matter, but rather, a celebration of the luxury that years of saving and fiscal responsibility afford you, such that money doesn’t matter.
That’s the funny thing about money – it doesn’t matter until it does and it does matter until it doesn’t. For more on why money matters (and why it doesn’t), I highly recommend taking a few minutes to watch this short talk.
4. Love can be a liability.
I learned this lesson by way of my career as a professional musical theater actor.
The reason so many artists and creatives struggle to negotiate livable wages is because they’re rarely willing to walk away from a chance to perform or do what they love for a living.
Loving what you do so much that you’re willing to do it for less than a livable wage is all well and good if it’s your hobby, but not when you’re trying to build a career.
I never want to like any one thing so much that I have to compromise what my time is worth to do it.
For me, the ultimate luxury isn’t necessarily doing what I love, but living and working on my own terms.
Doing what I want matters as much as being able to walk away when I want.
5. Health insurance is not a good enough reason to stay at a job you hate.
Whether it’s fear of losing employer sponsored health insurance, retirement contributions or other benefits, in the grand scheme of building a life and career on your terms, small considerations like these too often serve as unnecessary roadblocks.
I’m not saying you shouldn’t consider the financial implications of big choices, but in my experience, rising to the challenge of added risks and costs pays far greater rewards than continually holding back your potential.
6. Your worst-case scenario is liberating.
I like to think big and act even bigger, which occasionally results in life choices others consider way too risky.
Being single and child-free with no one to consider but myself certainly helps, but so does the thought of my worst-case scenario.
It might sound counterintuitive, but thinking through my worst-case scenario when making any major decision is hugely liberating.
What’s the worst that could happen if I fail and lose everything?
I’m surrounded by family, friends and community that would let me crash on their floor and probably even feed me for the small price of my help around the house. I’d go back to survival jobbing, waiting tables, babysitting and personal assisting while building my way back up. That leaves plenty of room for taking big risks, like starting a blog for a living.
7. Your worth is separate from what someone pays you.
I’m an avid believer in “charging your worth”, but I’ve found the implied connection between “worth” and “you” in that phrase to be a bit problematic.
When we say, “charge what you’re worth”, it’s easy to start confusing a monetary value like your salary with your self-worth, and goodness knows that’s a slippery slope. Instead, charge what your work is worth.
It’s also important not to discount context when talking price point. For example, if I write something for another blogger, I know I can’t charge what I’d charge a Fortune 500 company – it’s a completely different market and that plays a major role in shaping the price point.
It’s not someone’s budget that defines what your work is worth, just as it’s not how much you’re paid that defines your self-worth.
8. Work in service of others.
One of the biggest mistakes I see people make is following their dreams in service of themselves rather than in service of others – hell, I did it!
While I’m all for considering your own needs, it’s critical to remember that the crux of any successful business is not about what that business can do for its owners but what it can do for others.
People don’t pay you to be passionate or love what you do, they pay you to fulfill a need, provide a service and offer value to them.
This isn’t just about being a good person, it’s a basic economic principle, far too often overlooked when considering our own paths.
9. Execution trumps ideas.
As an entrepreneur, people love to tell me their ideas. As much as I like to philosophize, I don’t really care for ideas until they’ve been backed by some kind of action.
It doesn’t matter if the action has resulted in wild success or catastrophic failure so much as whether action has been taken.
The reality is, everyone has ideas all day long that could change their lives, maybe even change the world, but you have to do something with them before they become meaningful.
10. Don’t wait for permission.
Execution is just the first step in any great action plan – the next major hurdle is pushing past the idea of permission.
We’ve got more than enough resources these days to act and up level on our own without waiting for the traditional gatekeepers to come around and buy into our vision.
For example, I could be taking action, drafting my latest book, but if I wait around for permission from an agent or publisher to “let me” put it out there, it might as well still be an idea.
I’m not saying we shouldn’t be measured about the way we approach some projects, but the notions of traditional and accepted pathways can sometimes do more harm than good, standing in the way of dreams realized to their full potential.
11. Failure isn’t an objective.
As much as I consider failure inevitable on any pathway to success, I don’t like to fetishize failure in the way that’s become so prevalent. It’s not like we ask failures to come speak at graduation or give a TED talk. We ask people who failed, but ultimately became successful.
The reason failure is so important is that it’s an outcome of action, and action, rightly, should be celebrated.
When actions result in failure they require at least one more step before becoming successful – more action, better informed and repositioned to succeed based on lessons learned from previous failures.
12. Always aim for “Yes, and”.
There’s an unfortunate belief that saying yes to something means saying no to something else.
For example, choosing “money and career” means saying no to “travel and freedom” and vice versa. But those are false choices, as are most either/or decisions. You can choose not to choose.
You can choose to say “yes, and…” and find a way to enjoy all that you want, instead of succumbing to limiting ‘either/or’ defaults.
For more specifics on “yes, and” thinking and how to implement it, check out “Yes, And … Your Life”.
13. Let go of duality.
Every day seems more polarizing than the last, and in large part, I think it stems from an over adherence and dependency on duality – good vs. evil, right vs. wrong, etc.
I think we all know there’s far more nuance in this world, and that being for something doesn’t mean we’re against the other.
While it can feel more comfortable to compartmentalize and make simple judgments with duality, leaning into the grey grants us more tolerance, empathy and understanding, (and I can’t think of much more important than that).
14. Greatness happens in the grey.
Much like I’ve learned to exist in the grey ideologically, the notion of leaning into the in between has served me remarkably well in my career too.
The idea of choosing one path at the exclusion of others is far too limited for my liking. Actor or financial expert, why choose?
There’s no time like today to pursue a portfolio career, or better yet, create your own role combing the many skills and interests that are uniquely your own to meet needs in today’s business landscape.
It’s time we stopped asking ourselves what we want to be and start challenging ourselves to be all that we can be.
15. Allow your vision to be big, but not rigid.
One of my absolute favorite exercises is writing out my “dream bio” – a paragraph someone would use to introduce me if I accomplished everything I wanted in my career.
Mine includes some combination of national television host, Broadway star, best selling author and non-profit founder – clearly I know how to dream big.
I remind myself of that vision every day to make sure my day-to-day to-do list remains in alignment what I’ve set out to achieve. I also check-in with it regularly to make sure I adjust as necessary.
Every day offers new experiences that influence what we want the ideal vision of our life to look like. I like to check in often to make sure I’m working in service of what my dream bio is today and not whatever it was the last time I wrote it – a year or decade a go.
As Stephen Colbert put it, “Dreams can change. If we’d all stuck with our first dream the world would be overrun with cowboys and princesses.”
16. You can start building a bridge without knowing how to finish it.
I may want to be national TV personality, but I have no idea how I’m going to make it happen. That doesn’t mean I’m not taking steps toward it though – building my brand online, developing a video presence and appearing as a guest on as many national news broadcasts as possible.
There’s this bizarre notion that achieving a major milestone is like landing a giant leap. In my experience though, it’s more like taking the final step across bridge. The beauty of a bridge is that you don’t have to be able to see too far ahead to get to the other side – you just have to be able to take the next step.
It’s about following a direction more than it is about arriving at a destination.
17. The mind doesn’t work like a camera, it works like a projector.
The prism of our thoughts and experiences shapes our reality. Every person’s perception of what is is different based on their unique set of ideas and experiences.
Not only does this realization help dismiss the notion of absolute truths and foster greater empathy, it opens up a huge opportunity in every moment to think differently and enjoy a new experience of being alive.
18. Know yourself.
Confession, I don’t love dogs, I’m not fond of children and I work terribly under authority. These were all things that took me nearly 30 years to realize because I spent so long thinking I was “supposed” to love children, dogs and my bosses (or at least respect them).
Getting real with myself – the good, the bad, the strengths and the weaknesses – has helped me immensely when adapting to new environments, assessing new opportunities, and perhaps most importantly, finding my best fit in every circumstance.
19. Passion is the result, not the cause of taking action.
I didn’t dream up the idea of becoming an actress out of nowhere – I was in a play and I liked it, so I sought out more performing opportunities. In other words, I discovered my passion through doing, not thinking.
The prevailing myth of passion suggests that it arrives in some magical burst of inspiration, but in reality, passion is uncovered through action, exploration and work.
Like falling in love, you go out and explore different experiences with different people, staying mindful of opportunities that present themselves, exploring those that pique your interest and hopefully, stumble upon passion in the process.
For more on passion, check out 4 Important Truths to Pursuing Your Passion.
20. Take responsibility.
Even if something isn’t your fault, your reaction is your responsibility.
While that can be a tough pill to swallow, it’s also a hugely empowering way to realize your own power. When you take responsibility, you give yourself the opportunity to become the solution to any problem you’re facing.
21.Your network matters even more than you think.
Do you know why I’m still based in New York City, even though I can work from anywhere in the world? Because I’ve never experienced a place more full of people hustling hard to be at the top of their game across a broader cross section of industries.
Being surrounded by successful, inspiring people who dream and execute past points of my previous perceptions of possibility is intoxicating.
And it’s not just my remarkable professional network that I thank for my successes, it’s the network of lifelong friends and family that have been there to support and champion my efforts every step of the way.
I know everyone talks about how important networking is, so maybe this is one of those instances of hearing something vs. knowing it. The only thing I would add is go deep (as opposed to wide). Fewer, meaningful connections will serve you far better than loads of shallow encounters – especially when you approach them strategically.
For more on strategic networking check out the second half of this post – How to Make an Extra $1,000 Per Month.
In my view, the best thing you can take away from your twelve plus years of formal education is the ability and desire to learn more.
Not only does a lifestyle of learning make you infinitely more knowledgeable (and marketable), it also makes growth a habit.
23. Be mindful of your consumption to creation ratio.
As much as I love learning, spending my days consumed by podcasts, blog posts, TED talks and boat loads of online courses, I know that all the knowledge and inspiration in the world won’t do me much good unless I set aside time to implement it in my own creations and expressions.
24. Good health is good practice.
I can’t think of a more accessible or tangible metaphor for any long-term goal than my physical health. Fostering the daily discipline of healthy eating, exercise and general self-care gave me a framework for understanding how to approach every major milestone I’ve since sought to achieve.
I’m pretty sure it’s no accident that my small blog turned into a full-blown business the year I trained for and ran the New York City marathon. By undertaking a goal so overwhelming, I had no choice but to take it one step at a time and learn the practice of daily discipline.
In reflecting on race day, I’m instantly transported to the 16-mile mark. There’s no way in hell I would’ve finished if I kept thinking about the fact that I had ten more miles left to run. But by tapping into my breath, holding to my core and digging into my discipline to focus on the next step, I was able to keep going until the finish line. That approach has served me in every milestone moment since – physical and otherwise.
25. Gratitude is the ultimate antidote to dissatisfaction.
I had a serious negativity complex in my early 20s. Maybe it was the recession. Maybe it was the “starving artist” complex. Maybe it was struggling to find sanity in my relationships. Whatever the reason, I was consumed by nasty negativity so strong that my default response to how are you? was always some kind of gripe or grievance.
Enough viewings and readings of The Secret later, the practice of gratitude finally sunk in. And it really was a practice.
Even at the ripe age of 22, it was hard to rewire my brain to stop bitching. So I started my gratitude practice with something stupidly simple – writing down three things I was grateful for each day.
Eventually, I started noticing things to be grateful for in between journal entries and started saying thank you throughout my day. Thank you for this penny on the street. Thank you for this glimpse of sunshine. Thank you for this coffee and conversation.
By retraining my brain to focus on all the good I already had, I stopped noticing what was lacking.
26. Question everything.
I think it was some time in my teens that I realized mom and dad weren’t always right, but it took until my 20s to question my most revered sources.
No matter how prestigious or popular the source, thinking critically, asking questions and being unafraid to push back has helped me developed my most valuable skills – critical thinking and problem solving.
27. Time is the ultimate resource.
As much as I believe money matters, nothing trumps the value of time – you can’t get more of it, so don’t go wishing it away or blowing it living someone else’s vision for your life.
I’ve also come to recognize the enormous value of using my money to free up my time. Paying someone to clean my house or do my laundry is usually worth the couple of hours I regain in my week – as long as I can afford it.
28. Make time to be proactive.
Between the routine of the day-to-day and the onslaught of incoming requests from social media and email, it’s easy to get caught up in a cycle of reactionary responses.
Once a year, maybe twice, you might find yourself looking around and thinking, how did I get here? And then the cycle starts over again – sometimes after a short-lived attempt to make a change, sometimes right away.
There’s simply not enough time set aside for the things we need to do to bring us into alignment with where we want to go when we spend our whole day reacting to the inputs constantly coming our way.
I now set aside designated time for proactive activities and remain fiercely protective of those hours – scheduling them into my day as non-negotiable as brushing my teeth.
29. Invest in yourself.
Just as it’s important to dedicate time to becoming your best self, there’s tremendous value in dedicating a portion of your budget to becoming your best self as well.
As long as it’s built into your financial plan, investments in your growth and development can pay huge dividends.
I spent about $20,000 on my business last year.
That was my annual income just a few years ago. Now, it’s less than I made last month – so I guess it was a good investment 🙂
30. Success is not a zero sum game.
I won’t pretend I don’t feel the occasional twinge of jealousy or fear that I’m falling behind when I read about the many successes of my peers, but I’m also quick to remember that someone else’s success is not my loss.
In fact, it’s usually the opposite – a rising tide lifts all boats. Meaning the more success my peers and colleagues enjoy, the more there is to spread around and enjoy together.
In the end, I most enjoy the days that we all celebrate together. So thank you for being here and celebrating with me. Here’s to the next 30 years, the next 30 lessons learned and more!
What’s your greatest life lesson learned thus far?