We’re all on different paths, in different places, as different people, but in a lot of ways our journeys might have similarities. I wish I had the knowledge I do now when I was 20. Not so I could’ve been more successful in my career or gone more directly into a job I love, but so I didn’t hold myself back as much, held more compassion, found more joy and dreamed bigger. That’s my hope for you.

I won’t apologize if this feels a bit cringey because I know how meaningful each of these points are so please pause and let them sink in. Sit with them and take what helps you.

Anyways, here we go with advice for my 20-year-old self: 20 lessons I learned the hard way…

1. You will change. A lot

Who you are and what you care about will keep shifting as the world changes around you, as you experience different things, as you age and meet new people, encounter tragedies and blessings. You will always be you, but there will be several versions of you. This is why it’s key to not get too locked into a certain expectation, plan, goal, or career move – your needs and wants will very likely jump around. Disappointments, mishaps, failures, and inconveniences will pass.

2. People make the place.

The people you work with have a big impact on your day-to-day job satisfaction. When hunting for jobs or considering a change, realize that a lot of your working experience is impacted by your manager, the colleagues you interact with, the company culture, and the structure of your job. Plenty of people couldn’t care less about their actual day-to-day tasks, but getting to spend time with really great coworkers makes it more than worthwhile.

3. You don’t know until you try it.

There is no other way around it. Get into a cycle of experimenting, reflecting, and learning. Take note of tasks you’d like to learn, roles to try on, personas to adopt, then test out each one. You might surprise yourself. You are a growing, shapeshifting individual and you need to get out of your comfort zone. Keep an open mind, you might not like the job you’ve been working towards for years, you might love one you never even heard of. That’s okay, keep experimenting.

4. Reality will not live up to your expectations.

Daydreaming about wearing your power suit into your corner office with your Louboutins clacking on the marble floor while others clamor for your valuable attention… is fun but we really can start to feel a bit entitled or ‘above it all’ when we’re asked to do menial tasks. Whatever you expect your job, career, or life to look like, reality will hit you with disappointment but also pleasant surprises. Be ready to go with the flow and be present for it.

5. You can count on things not going according to plan.

Relatedly, you’ll never see the changes coming, the doors that open, or people you’ll meet along the way. If you spend ages creating an incredibly detailed 5-year plan and then put your head down and plow through it, you’ll miss so many wonderful opportunities. And as you already know, you’ll change so much that you probably won’t want the same things five years on. Stay curious and open, don’t sit still but also don’t stick so close to a set plan that you give up any alternative paths.

6. You are capable of way more than you currently believe.

You will achieve some pretty amazing things in your life. You’ll get more courageous and powerful one step at a time. Until you look back with shock to see how far you’ve come. Don’t tell yourself you can’t do something, just look at the step in front of you and try to do that, then the one after that. You’ll learn and grow as you progress even if you sometimes take a few steps back or do a little cha cha to the side. Keep going.

7. It’s not what you know, it’s who you know.

It really is about the people you know and surround yourself with, and networking is really just about connecting with other people. It doesn’t have to be scary, it’s a chance to practice putting yourself out there and finding like-minded people. Meanwhile, the requirements for ‘what’ you need to know will keep changing as you move along your career path. In fact, most of what you’ll need to know will actually be learned on the job.

8. You will never feel like enough if you rely on others to tell you you are.

Measuring self-worth on validation from others will never make you feel worthy. Whether it’s getting enough ‘likes’ on social media or needing your boss to give you a gold star on that last report, you are the only one who can genuinely see your worth. If you need to step up your self-love game to make it happen, start practicing today. Recognize your worth, see the strength you hold, and believe in your value.

9. You have to put yourself out there in order to grow and live.

You have to take risks and make mistakes. This one is so important it’s a theme throughout this list. The most alive you’ll ever feel is when you’re bearing your soul to the world, being vulnerable with what you truly care about. If you don’t raise your hand, step forward, and take chances, you will not achieve your goals. Start by taking small intentional risks that make you nervous and then keep taking one more scary step until you’re embracing the fear.

10. Your plans, thoughts, and ambitions are heavily influenced by other people.

It will take a lot of trial, error, and reflection to figure out what you really want. Women especially tend to internalize messages from our family, friends, and community at large (likely due to the desire to please others). We take on dreams that might not have stemmed purely from our own imagination. Most people don’t know what they want to be when they grow up, and we just keep trying to figure it out as we go along.

11. Get to know yourself.

Develop a relationship with yourself to know what you like and don’t, what makes you feel alive and what drains you, nurture this throughout your life as you evolve. Practicing mindfulness and intentionally growing your self-awareness will not only bring you loads of clarity but also help you become more resilient, set boundaries, demonstrate your value, and advocate for yourself. We are all incredibly unique, figure out what makes you you.

12. Your inner critic will hold you back, befriend her now.

Learning to distance yourself from the nonsense your inner critic is constantly spewing, to check and counter what she says on a daily basis, is the difference between holding yourself back versus giving yourself your best shot. Notice what the critic is saying, the language and tone being used. Challenge yourself to think if you would speak that way to your best friend. If not, why treat yourself that way? What damage is that doing? What would it be like to talk to yourself with compassion instead?

13. Gender equality at work has come a long way but still has a long way to go.

As of 2024, bias is alive and well and according to the Global Gender Gap Report we have decades to go before we reach parity. Recognize that subtle differences in a business world built by men might mean you aren’t getting the visibility and opportunities you deserve. Don’t let the world make you feel like you’re the problem. The world is changing but slowly. For now, you can raise awareness of gender and other individual differences to more effectively navigate and succeed today.

14. Don’t take a backseat, be the leader of your professional journey.

We often wait, work really hard at our current jobs, and assume others will tap us for opportunities they think are right for us. But it’s actually on you to figure out where you want to go, learn what you need to, and take the chances that will get you there. It’s okay to coast sometimes, prioritize your personal life, and let your career take the backseat. But if you have specific dreams and goals, take ownership of your future.

15. Take your career seriously, but don’t define yourself by it.

That being said, your career is a marathon, trying to sprint to the finish line will have you dropping out or burning out far too soon. Work is only one part of who you are, even if you are incredibly ambitious and have lofty goals. Don’t underestimate the importance of exploring interests and hobbies outside of your main source of income. Take on projects, look into volunteering opportunities. Join a sports team or a language class. Stay curious, find what gives your life meaning, and make your well-being a priority.

16. Your voice is your most powerful tool.

You are the only one with your unique set of experiences and perspectives. You will likely see things differently, ask different questions, say different things. Sometimes you’ll say the wrong thing, but most of the time you will deliver value by speaking up and sharing your point of view. Don’t hide it. There were so many times I stayed quiet when I had something to say. I wish I hadn’t. Mainly because I missed out on learning how to deal with not saying the right thing.

17. You will never have all the answers.

Know what you don’t know, and be willing to admit those knowledge gaps and rethink things. You literally can’t know everything, people who pretend to, tend to be poor leaders. Instead, recognize where your knowledge stops, find experts who fill those gaps, and surround yourself with people who are smarter than you. That is how to be not only an effective leader, but also an empowering one for those in your orbit.

18. It’s never too late to start over.

Skills are transferable and you don’t just gain key skills on the job, you build that mastery with hobbies, sports, caregiving, volunteering, etc. Too many women stick to their chosen career path, fearing having to “start over” if they went after what they truly wanted. But you don’t have to start at the beginning, no matter how different the career paths may seem, find the connection and position yourself as the perfect link to provide a fresh perspective.

19. It’s okay to be wrong.

Even if you’re working somewhere with a blame culture or a toxic manager. If they don’t let you be wrong sometimes, that’s on them. If you don’t get stuff wrong, you’ll rarely get it right – a clear theme in this list. That’s how we grow, but our guttural reaction to being wrong is so painful that fearing failure is a debilitating issue. Luckily, this one gets better with practice. In the spirit of learning by doing, go ahead and get a few things wrong.

20. There is meaning and joy in your everyday life, seek it out.

In each step of our career, we’re often looking to what’s next. “I’ll be happy when I get that promotion, make more money, work less hours, etc.” We focus on what could be better about our current situation, and miss the small things that are actually alright, or even pretty great – the colleague you share a laugh with, the great coffee place next door to work, that one client you love to work with. I ask you to seek out the joy in each and every day.

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Regardless if any of these resonated with you, I hope you take a moment to reflect on what you’ve learned in the past chapter of your life and also what you think your future self might want you to know now.