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If I could send a letter to my 22 year old self, it would start like this:
“Hey Me. It’s You.
First: I love your flower skirt. Please don’t donate that one to Goodwill, you’ll regret it.
Second: Listen, I know what everyone’s trying to tell you.
They’re trying to gently explain that this writer thing isn’t going to pan out.
They’re trying to imply — with love — that you’re nuts for going freelance, or trying to start your own company when you’d be classified as “entry level” in pretty much any agency you apply to (Though, let’s be real, all those free hours you spent interning should really count for more. #millenialproblems).
I know you’re doubting yourself, every minute of every day.
I know that despite the clients you’re attracting, the work you’re creating, and the money you could make, you’re terrified it’s all temporary, and soon your inexperience will to catch up with you — and you’ll make one major blunder that sinks the whole ship.
I know everyone else you meet in your field has 5, 10, even 20 years on you, and whenever anyone asks you your age you break out into a cold sweat.
I know almost no one believes you can do this, except maybe a couple of your best friend and family members.
But I believe you. And you believe you. At the end of the day, that’s all you need.
Keep your head down, and keep pushing. You’re going to be better than alright.
See you in a few years.
Can I be honest about something?
I turned 28 a few days ago. And even as I start flirting with 30, my age is still my biggest frustration.
Spilling that number — which feels like it should be totally arbitrary after 25, when my frontal lobe stopped developing — has never felt comfortable for me.
Since the beginning of my business, my age has always inspired a reaction: of surprise, of doubt (even distrust), or of total bewilderment.
(And I’m not even that young or rich! Seriously, here are at least 40 people who were millionaires before they were 20. I’m not that extraordinary.)
Don’t get me wrong: It’s felt cool to be called a wunderkind once or twice. But historically, by no real fault than society’s expectations, my age has largely only served to make me feel reduced.
Last weekend, in my final days of 27, I was sitting in a hotel lobby with a client friend.
We’d both been speakers at a conference, and had spent the last few weeks working closely on her launch. Margaritas in hand, we were laughing about the niche we’re both a part of; toasting its past, present, and future.
Then she asked how old I was turning, and I felt that familiar twinge in my chest.
But I’m older now. I told myself. We’re getting into “take me seriously” age territory. Just spill it, Weiss.
Her eyes widened. My heart sank.
What followed over the next 90 seconds is the same conversation that’s played out for me, over and over again, for almost 6 years now.
Her: Oh my god, you’re a baby! I didn’t realize you were so young — you have so much experience and —
Me: Yeah, I got started at 22! But I’ve looked 30+ for a few years, haha, so…
Her: Oh god, no no! I’m not saying you look older, I’m saying —
Me: Oh totally, I wasn’t offended, I’ve just always looked older, so people assume I’m older, and um…
Maybe I should add a “P.S.” to that letter-to-self: We never age out of awkwardness, or making terrible jokes to diffuse situations. Sorry.
But I choose to be open about these stories, and these challenges, because for every 5 conversations I have where someone older is surprised by my age?
I have 1 conversation with someone younger, more hesitant, and as determined as I was 6 years ago to be their own boss.
Those are the conversations that mater most to me.
And these young bucks, full of energy and excitement and fire, all come to me with similar challenges:
- I work really hard, but no one else my age is taken seriously. Why should I be?
- I’m done being an intern, but everyone’s telling me to “earn my stripes”. I’ve worked for FREE for years for multiple companies. Where my stripes at?
- I feel like I’m ready to do this, but everyone’s telling me to wait ’til I’m older. Are they right?
- None of my friends are freelancers/entrepreneurs. Some have tried, but they failed. Should I take that as a sign I won’t do well?
Here’s what I say to them, and what I’d say to you (whether you’re 19, 39, or 80):
Entrepreneurship, at its core, is an extended exercise in both self-trust and self-reliance (and, in some awkward hotel lobby moments, self-depreciation).
That means the only person who will ever know if you can really do this is… you.
(Not your parents, or your best friend, or your current boss. You.)
The only person who can be certain you’ll put in the work to create the success you want is you.
The only person who fully understands your instincts, skill set, and determination level is you.
So, what do you think? Are you ready, according to you?
Let me be clear here: “Ready” doesn’t feel like unshakeable confidence and bravado.
(That’s not “ready”, that’s a light show.)
Ready means you can feel, in your bones, that you can really do something — and make money doing it — if you’d just muscle yourself forward.
Ready feels like the willingness to dip your toe, then your whole foot, and then your entire body into the water and swim for your life — even if you know the current’s rough.
Ready is that steady, calm feeling buried under all those layers of doubt the outside world has seeded into you — the feeling that assures you that whatever they might say, you know yourself. And you can do this.
Ready is focused. Ready is brave. Ready has no illusions about the journey ahead, but is excited about the challenge.
And trust me, my fellow young bloods: you’ll need to be ready, because you’re going to be treated differently for a while.
(Remember: No one needs to know your age. Don’t lie, but you don’t have to lay it right out on the table.)
People are going to tell you you can’t, shouldn’t, or mustn’t just based on the number of times you’ve personally orbited the sun.
They’ll tilt their heads, and click their tongues, and talk to each other privately about whether or not they feel you can do this, and why.
They might place bets. They might try to talk you out of it and feel they’re doing you a service.
But here’s the thing:
They don’t matter. Only you do.
Only you get this one precious, wild life, with all your talent, grit, and beautiful ideas to do whatever you like with.
Could you still fail? Hell yeah! And you should plan to, because you will.
But everybody fails, and everybody stumbles.
Being young may require you to topple over an extra time or two, but besides that? You’ll be learning and growing just like anybody 5, 10, or 20 years your senior.
If failure doesn’t frighten you enough to hold you back — and won’t bankrupt you?
Go for it.
Trust the “ready” you feel — it will guide you well for the rest of your life.
Listen to the voice within you. It’s the only one who’ll be accompanying you on this journey.
And if it feels right, despite everything?
You have my permission to launch.
… Not that you ever needed it to begin with.
This is it. There’s no better time.