Want to Take a Big Leap, But Don’t Feel Ready? That’s How You Know It’s Time to Start.

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What are you really excited to do in the future, but you just don’t “feel ready” to do yet?

When I say excited, I don’t mean something you’re good at. I mean, the thing that completely, totally lights you up. Like, if you were looking in a mirror watching yourself talk about that thing, you’d resemble a kid who just got to Disney World for the first time. 

What’s that thing? 

Write it down now. On paper. Writing it down is about 100x’s more powerful than thinking it in your head.

…Got it?

Now, list off all the reasons you don’t feel like you’re ready. 

If I had to guess, I bet at least one of the following things is on your “What’s stopping me from chasing my dream” list:

  • There isn’t enough time in the day.
  • I don’t have the money to pursue what I want to do.
  • My personal network/audience isn’t big enough yet.
  • I don’t have the skills required to make it happen.
  • I have too many other things on my to-do list.
  • I don’t have a concrete plan.
  • I need to do X, Y, and/or Z first.

…Am I right?

I can tell you that, for me, when it comes to the two BIG things that get me really, really, really excited right now and I absolutely know beyond a shadow of a doubt I want to do, every single one of the above considerations is on my personal “What’s stopping me” list. Every. Single. One.

Here’s the truth we all know on a cellular level, when we brush away the layers of limiting beliefs and bullshit stories we keep telling ourselves and other people about why we’re not ready yet:

They are excuses.

We might as well cross off “Why I’m not ready yet,” and substitute it for, “All the excuses I’m giving myself to mask my massive resistance and fear.”

Here’s the thing about all of these considerations:

1.) There isn’t enough time in the day. 

…You’re not going to get any less busy in the future. If you do get some more time on your hands, you’ll find a way to waste it (Parkinson’s Law). And, every day you don’t do what you really want to do is a day you’re never going to get back. You have a lot less time than you think to make your dreams happen. There’s not enough time in the day to do what you feel called and compelled to do? Then, what exactly are you spending your time doing? 

2.) I don’t have the money to pursue what I want to do.

…Neither did Michael Jordan, Oprah, Howard Schultz, Steve Jobs, or most other aspirational leaders when they first started. But you know what? They got scrappy and resourceful. No job was beneath them. They knew what they wanted, and were willing to do whatever it was going to take to make it happen. How are you any different?

3.) My personal network/audience isn’t big enough yet.

…So what are you waiting for? Set aside time in your calendar to connect with new people every week. Tweet at someone (consistently) you want to build a relationship with. Use LinkedIn to connect with people you admire—and actually follow up with them from time to time. Come to every conversation with something to offer, and some thoughtful questions to ask.

Create a simple website (nothing crazy) and use Mailchimp to build out an email list. Export all of your email contacts (the worse thing that could happen is they unsubscribe). Write the first blog post. Then the second. Then the third. Share what you create. Connect the great people you meet to one another. 

One coffee meeting or Skype call, tweet, project, or blog post at a time, you’ll build yourself a meaningful network/audience. 

4.) I don’t have the skills required to make it happen.

…Then, go get the skills. You can’t build a website because you aren’t a coder? Well, the only way you’re going to learn is to start building the damn website! You can’t be in the legal industry because you don’t have a J.D.? Well, start studying for your LSAT! Or, perhaps even better, figure out how you can use your current passions/skills and apply them at a pre-existing law firm. 

The skills aren’t going to magically acquire themselves. If you really want something, but it takes learning something else first, then get to work on learning that something else.

5.) I have too many other things on my to-do list. 

…Are they more important to you than your dream? What are you going to regret more in 10 years? Quitting some of the things on your current to-do list? Or, never getting around to what you really want to do? If there are important things you truly must get done (bills, certain chores, family matters, etc.), then take are of those. Obviously, don’t drop the ball on necessities. The point here is to re-examine that list. Because most of it is probably stuff you don’t even want or need to do. 

What can you quit? What can you delegate? How can you get creative about getting to a needed end goal faster or easier (i.e. automatic bill pay, hiring a babysitter an extra night per week, batch tasking your chores, outsourcing your taxes, etc.)? 

6.) I don’t have a concrete plan.

…You know how you get one? All it takes is a pen, a piece of paper (or more if you write a lot), and some S.P.A.C.E. to think and dream and scheme. Most of us never give ourselves the space. We get stuck in a mental state of resistance. We’d be shocked to learn that all it takes to breakthrough is some hard work and willingness to push through the inevitable but breakthrough-able wall of pain that separates us from the life we’ve got and the life we want. You’re lacking a plan? All you need is commitment and a quiet weekend. 

You’ve got this. You’re so close already. 

7.) I need to do X, Y, and/or Z first. 

…(1) Do you really? Or, are you allowing your resistance to block you from problem solving creatively? What path are you not seeing or creating because you’ve convinced yourself that there’s only one way to live out your dream?

(2) If you really need to do X, Y and/or Z first, then get busy. X, Y, and Z aren’t going to disappear! In fact, the more you put them off, the bigger they’ll get. They will zap away your spirit. They will deplete your intellectual and emotional energy. They will replace those things with fear, worry, anxiety, and regret. If there are things you know you need to do, get started on it now. There’s never going to be a better time. I promise you that.

Whatever excuses you’ve got, it’s time to drop them. 

If you want something, start before you feel ready. 

Because, you know what? Running in the direction of what really, truly excites you is exactly what will make you feel *beyond ready.*

But, by then, you’ll already know that for sure. Because you’ll be doing the things you’ve always wanted to do. And you’ll be watching the fruits that come as a natural byproduct of the labor required to push past resistance and make epic shit happen. 

You want something? Go get it.

You’ve got everything it takes, as you are, right now.

You’re more than ready. 

Now is Exactly Where You Should Be

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It feels like everyone I’ve talked to lately is in a period of transition.

In and out of careers.

In and out of school.

In and out of their healthiest selves.

In and out of relationships.

In and out of love.

In and out of friendships.

In and out of faith.

In and out of town.

If I had to assign a handful of words to describe the overwhelming majority of conversations I’ve had recently, it would be these:

AMBIGUITY. 

UNCERTAINTY.

DOUBT.

TRANSITION.

TRANSFORMATION.

This is shocking to me, this recurring theme. Mostly because the last several months of my own life have felt like a complete upheaval. 

Heartbreaking, at worst. Trailblazing, at best. Transformational, consistently.

I don’t know if it’s some freak coincidence. Or the law of attraction. Or if everyone in the world is operating on a collective wavelength that is stronger than any of our individual ones. 

All I know for sure is that this feels like a time of transition for many of us. 

So, this note is one of encouragement for anyone going through a season of ambiguity, uncertainty, doubt, transition, transformation. Myself not excluded. 

I know this sucks right now. 

I know you’d rather just know. That you’re anxious for perfect clarity. You’re ready to land a new job. You want to move quickly past the heartbreak. You want to complete things that are incomplete. You are frustrated because you feel so unsettled, lost, indecisive.

I really do know. You’re not alone. Everyone around you is fighting their own private battles, too. 

We’re taught in our culture to seek out immediate clarity. Fix everything as soon as possible. Check things off our to-do list. Don’t get down on yourself. Chase after joy. “Good things come to those who work their asses off.” Stop procrastinating. The answers will come to you when you start to move. Move faster. Start making some decisions. Do what feels “right.”

Not that you need my permission, but just in case you’re waiting for a sign, this is it:

Fuck all of that advice. 

You know what happens when you listen to those motivational maxims that play in our culture on repeat? 

You lose touch with your inner voice. You know, the one that belongs solely to you. 

You start to break promises to others and yourself under the guise that something doesn’t feel “right,” when really, you’re just avoiding the inevitable pain that comes along with transition.

You start to read self-help books instead of giving yourself the space to b.r.e.a.t.h.e.

You make rash decisions because you’d rather decide something than admit that perhaps the greatest lesson in this season of your life is learning to find comfort in the midst of delicious ambiguity. 

You check the wrong things off your to-do list. Stuff that doesn’t even matter to you. Stuff that isn’t aligned with your values or desires. 

You begin to numb yourself with food or alcohol or bad television or overspending on crap you don’t even want or need, because you’ve been taught to avoid pain at all costs and immediately gratify yourself instead.

You forget that some things will be massively incomplete in your life, and remain that way for some time. Not everything can be “fixed.” Once things are said, done, experienced, they cannot be taken back. Stop trying to erase things you’re meant to learn from. Stop trying to take a Neosporin stick to scars that make you more beautiful and real than you know.

You move faster, when what your entire body is screaming for is STILLNESS. Time to calm your heart and mind. Time to grieve the things you’ve lost. Time to do absolutely nothing for a little while. Time to take in the current season of your life. Time to process.  Time to cry. Time to forgive. Time to love yourself again.

Everything you’ve encountered up until this moment is perfect. 

I know that’s hard to see when you’re feeling confused, exhausted, heartbroken, anxious, and unsure. I really do know. 

But I’m also learning that things turn out to be exactly what they need to be. Some stories don’t have a clear beginning, middle, and end. You won’t always understand everything that’s happening to you. Maybe not now, maybe not ever. 

If you’re in a period of transition, you don’t need to be anywhere but where you are. It’s okay to take some time to savor nothingness. It’s okay to not know the answers. It’s okay to be unsure about what you want to do next in your career. It’s okay if you’re procrastinating about something. It’s okay to be going through massive amounts of pain. 

Every job, relationship, friendship, family member, unfortunate circumstance, health situation, birth, death…

All of it is perfect. All of it is full of extremely important lessons that, if learned, will make you stronger, wiser, more open-hearted, more open-minded, more free, and more yourself than ever before.

All you’re responsible for is trusting that. 

It all brought you to the now. 

…And now?

Now is right on time. 

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How to Be Grateful for the Stuff Most People Complain About

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Can you imagine how amazing life would be if you were thankful for all the things most people spend all their energy hating, being annoyed by, or trying to avoid? 

You’d have so much…space.

Space to love. Space to get clarity. Space to feel light, in body and spirit. Space to be happy.

Here’s the invitation.

(1) Write down a list of everything you don’t like or try to avoid.

Here are some of the things on my list:

  1. People who don’t say “thank you” when you hold a door open for them.
  2. People who want to meet for coffee and take the most inefficient approach possible. You know, when it takes a dozen email exchanges to get a 20-minute meeting on the calendar with them.
  3. When I pay for a lot for something that goes on sale a day later.
  4. Taxi cabs. To this day, I cringe at how much they cost.

(2) Write down why you’re grateful for each of those things on your list. 

Here is mine: 

  1. People who don’t say “thank you” when you hold a door open for them. I’ve got arms to hold the door open, and an opportunity to practice unconditional grace. 
  2. People who want to meet for coffee and take the most inefficient approach possible. I’m lucky to have people who care to meet me and get to know me. 
  3. When I pay for a lot for something that goes on sale a day later. I had the financial means to buy it at full-price.
  4. Taxi cabs. To this day, I cringe at how much they cost. I can get home safely at night, and that’s worth a lot more than a cab ride. 

The objective of this exercise is, of course, the experience of gratitude. 

If we can be grateful for the things we don’t love, can you imagine how grateful we’ll begin to feel about the most beautiful things that come our way? 

Gratitude is one of the best feelings in the world. It’s also a choice. 

If you want to feel great, choose gratitude every single day. Start with the hard stuff…

Actively practice being grateful for the stuff most people complain about.

What Do You Do When it Rains?

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We have to remember that sometimes—often—there’s a fundamental difference between what we want for ourselves and what the universe wants for us. 

We want to feel successful about a ton of external stuff. Finding a great love, building a hot startup, completing a hard project, making a million dollars, writing a bestselling book, getting into grad school, landing the dream job.

The universe could care less about that stuff. It’s just interested in who we are on the inside. How are hearts are growing, breaking, learning, repairing, building up again. Bigger. Stronger. Richer.

It’s why sometimes things happen to us that don’t fit into our plans. It’s why we face adversity. It’s why our choices come with consequences—sometimes expected, sometimes not. 

We try to understand the circumstances we don’t want and the missteps we took in the context of our little plans. 

We take our gaze off the bigger plan.

It’s not about the stuff we acquire or the money we earn. It’s not about the weight we gain or shed. It’s not about the love we found and lost. It’s not about the company we started and failed at. 

It’s about our inner strength. It’s about who we were, and who we are, and who we’re meant to become.

On the inside

Earlier today, I was thinking about why certain things are happening in my life. Why is this happening to me? How will I overcome this? How will I move forward? 

As I thought about the things weighing most heavily on me, and how they don’t fit neatly into my goals or plans, I went outside. 

And it started to rain. I mean, pouring rain. Can’t see more than a few feet in front of you kind of rain. 

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It somehow felt completely perfect. Like a serendipitous sign at exactly the right time. 

It felt like God’s way of reminding me that I’m assessing my life in relation to my small plans. Not to the Universe’s big one. 

When I reassess what’s been weighing on me through the lens of how it’s meant to shape me on the inside, it makes complete sense. All of it.

I need the adversity. I need the heartbreak. I need the unexpected.

We all do, don’t we?

We need to be wildly thrown off course in order to learn how to adventure our way back. 

We need to breakdown to build up—we can’t build a big castle on top of a small house. 

We need the stunning failures. They force us to rebuild. And it is in the rebuilding that we discover we can overcome and accomplish anything. 

We need to feel heartbroken. The rush of overwhelming emotion that comes with it is a reminder that we’re alive; that it’s a blessing to feel anything at all. 

We need to lose people we love so we know what’s worth holding on to.

The things we think are curses are often our greatest blessings. They teach us the most. They shape us the most. 

It’s not about running inside and hiding from the downpour. It’s about embracing the feeling of raindrops as they kiss your skin.

It’s about embracing the hardships that are kissing your life. 

Hearts still beat when they break. 

Are you focusing on the breaking…or the beating?

Focus on the beating. 

…Always focus on the beating.

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The Personal Mission Every Human Being Has in Common

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"Just Be Yourself."

It sounds so cliche, right?

I don’t like cliche expressions. I really don’t. They feel watered down and entirely inauthentic. 

But every now and again, you come across a cliche expression that is perfectly spot on. And you wish it weren’t cliche because you want people to truly, deeply, profoundly get it. 

That’s how I feel about the expression, “Just be yourself.”

I’ve read thousands of inspirational stories and books. I’ve written and edited countless inspiration-driven articles. I’ve met and interviewed hundreds of inspiring people. And when I think about the books and stories that resonate the most, the articles that perform the best, and the people I adore and look up to more than all the rest, they all have one thing in common:

They scream authenticity. 

In other words, they scream, “I’m nobody but myself, and I love who I am. Imperfections and strengths and god-given gifts…all of it. “

I truly believe that the underlying mission we all have in common in life is this:

To be relentlessly, passionately, fully, unapologetically more and more of who we really are. 

Life is a process of learning about what moves us, triggers us, drives us, ticks us off, makes us angry, gives us hope. It’s about discovering and pursuing opportunities and relationships that expand our hearts and minds—ones that call us to love bigger and better. 

I think success, quite simply, is when we can be really ourselves.

If I’m being totally vulnerable here, I’m not even close to being completely myself all of the time. 

I just got back from a conference and spent half the time wondering how I fit in, if I was relevant, what total strangers thought of me, and whether those I engaged with found me interesting. I was super in my head. I think most of the people—even (and maybe especially) the speakers, conference organizers, and thought leaders—were just as in their heads as I was. 

I feel the best about life whenever I’m doing work, collaborating with partners, meeting with friends, starting relationships, and falling in love with people and situations that understand and catalyze me being, well…me. 

Isn’t that what we’re all after? I don’t even think it’s that we’re all trying so hard to be other people. We are just scared that who we are isn’t enough. So, we resort to copying others who are—you guessed it—very much themselves. 

But this is hands down one of the most enormous lies we tell ourselves: that we are not enough. 

It’s fucking absurd actually. Because we are so damn perfectly enough. 

If you’re reading this right now, I really want you to hear this loud and clear:

YOU ARE MORE THAN ENOUGH.

YOU ARE SO MUCH MORE THAN ENOUGH.

Whoever you are right now is absolutely beautiful. You think you’re too fat? Too thin? Too dumb? Too undereducated? Too poor? Too unsuccessful? Too introverted? Too loud? Too tired? Too afraid of love? Too anxious for love? 

Yeah. You know what that’s called? That’s called being human. 

By all means, if you don’t like the way something is, change it. But change it because it doesn’t align with who YOU truly are now, or the person you were truly meant to blossom into. 

Everything you’re learning right now is exactly perfect. Your struggles, fears, heartache, pain, lack of clarity, family issues, relationship struggles, health condition…you’re supposed to be going through what you are going through right now. 

Why? 

Because everything you’re experiencing is a highly teachable moment, and you need it to discover things about yourself you don’t know yet. And you know why you need to discover those things? 

Bingo. You got it:

So you can become more and more and more yourself. 

It’s as simple as that. I’m looking everyone reading this deeply in the eyes right now. 

If you’re a breathing, learning, imperfect human being looking to be an increasingly better, fuller version of yourself and live a life on fire, it all whittles down to this very simple lesson:

You’re alive to become more yourself. 

Because whatever it is you’re uniquely fantastic at is exactly what the world needs to be a more alive place.

This expression is cliche because it’s so damn true. 

Put it on a bumper sticker. Write it in your journal. Hang it in a frame and put it up on your wall. Tattoo it on your body if you need to.

And while you’re at it…

JUST BE YOURSELF. 

It’s Time to Take a Risk, Sweetheart.

If you’re reading this right now, there’s something that you want. 

And the reason you don’t have it is because you’re afraid. You’ve given yourself a list of reasons why you can’t have that thing, why it isn’t possible, why you don’t have what it takes to change your own life. 

Maybe you want to get in the best shape of your life. Maybe you want to have a super honest, vulnerable conversation with the person you love. Maybe you want to forgive someone—perhaps even yourself—for something that happened in the past. Maybe you want to be closer to your family. Maybe you want to quit a job that’s sucking the life out of you. Maybe you want to run a marathon. Maybe you want to drive across the country and tell stories.

I’ve written every single day this year. I don’t have all of the answers. I can’t tell you what’s going to happen if you take a chance and go get what you want or need. It may not work out at all the way you’re imagining it will in your head. 

But I’m asking you to trust me when I say that the biggest risk you could ever take is the route of potential (and probable) regret. You simply have to do what it is in your heart you really want to do. Don’t hesitate. Don’t be afraid. 

If you want something badly enough, and you make the decision to go make it happen, one of two things will occur:

(1) You’ll get exactly what you’re after and then some, no matter how the logistics work out. You’ll get that clarity, forgiveness, love, honesty, vulnerability, friendship, trust, career, etc. that you’ve been waiting for and dreaming of. This is the inevitable byproduct of being bold enough to chase what you really, truly want.

Fortune always favors the bold. All you need to do is give fortune the chance to work its magic. 

(2) What you want isn’t what you need. This happens sometimes. You can be really hell bent on an outcome, but it may not at all be what is best for you, given the incredible plan that the world actually does have in store for you. 

If you keep doing absolutely everything in your power and still, nothing is happening, you’re either:

(a) Not really doing everything in your power. Keep pushing and learning and risking. Your work isn’t over yet. Don’t give up right before the tide is going to turn. This is the point where you need to push yourself to think about how much you really want the thing you want. If you decide you really, really want something, stop giving up so soon! You can do this. Keep going.

(b) It’s truly not supposed to happen. Your desires are clouding reality and/or you’re playing small. If this happens to be the case, you’ll know it for sure so long as you make a commitment to constantly remaining open on your journey. And the universe will, again, reward you for being brave enough to take a leap anyway. It will reward you with the knowledge, wisdom, circumstance, relationship, or just plain faith to redirect your life and get on the road that was built just for you. 

Are you getting my vibe here? 

It’s time. 

Stop with the excuses. Stop telling yourself you can’t. Stop creating exceptions for yourself. 

If you want an exceptional, bold life, you need to stop thinking and doing mediocre things. 

Your time is now. There will never be a better time. 

So take every chance you get. 

And drop every fear you have. 

Because it’s time to take that risk, sweetheart.

When You Say, “I’m a Perfectionist,” I Hear, “I Don’t Think I’m Good Enough.”

My good friend Sean Johnson recently shared a piece of advice his dad used to give him. It goes something like this:

"In life, you’ll always be juggling multiple balls at once. And, at some point, it’s a guarantee that one or more of those balls will drop. Having a successful life is a matter of knowing which balls are made of rubber and which are made of glass. Drop accordingly." 

I can’t stop thinking about this advice lately. 

I’ve spent a lot of my life trying not to drop any balls, but continue to add more of them to my metaphorical plate. In other words, I have “I need to be perfect” syndrome. 

What the hell is that about, right? 

I think people wear “I’m a perfectionist” like it’s a badge of honor. It has somehow become synonymous with, “I’m an A player,” or, “I work really hard.” 

Truthfully, as a recovering perfectionist, I know it doesn’t mean either of those things. 

What it really means is, “I worry about not being good enough,” or, “I have a ton of fear about how people will judge my work, so I find mundane excuses to not ship stuff out and into the world.”

Perfectionism, for the most part, really sucks. 

When we try to force our imperfect selves to lead perfect lives, what happens is we start juggling more balls than we can handle. We juggle stuff that doesn’t mean much to us because we don’t know how to say “no” or simply don’t know what our priorities are. We forget that some balls are made of rubber and some are made of glass. And most tragically, we drop the glass balls because we don’t know any better. 

Rubber Ball Examples: 

  • Most business decisions and outcomes
  • Eating one unhealthy meal 
  • Not having the resources (financial, time, etc.) to do get something we really want the moment we want it
  • Sporadic disagreements with family, friends, lovers, and colleagues
  • Not getting all the way through our to-do lists

Glass Ball Examples:

  • Lacking integrity in business decisions and reactions to outcomes
  • Understanding your spirituality
  • Devoting time to being fully present with people you love
  • Not taking care of your body for prolonged periods of time
  • Spending (a lot) of money you don’t have on things you don’t really need for short-term satiation
  • Not being open to the greatest love of your life because you’re afraid of getting hurt

We’ll drop the glass balls. We’ll close ourselves off from love, stop getting adequate sleep, eat crappy food, not exercise, claim “agnosticism,” take shortcuts in business and relationships that might hurt or short change others because it’s easier, and allow ourselves to become easily distracted by shit that doesn’t really matter in the long run. 

And we do this all to preserve the rubber balls—working ourselves into the ground, caught in a cycle of making and spending more money on irrelevant stuff that we won’t remember when we’re 80-years-old, and spending so much time on “productivity” that we forget to actually accomplish worthwhile things. 

Success isn’t about forcing yourself to juggle more and more balls. It’s not about not dropping any of them, either. 

Success is simply this:

  1. Choosing the balls you want to juggle carefully
  2. Not letting the fear of dropping a ball disable you from doing noteworthy shit
  3. Knowing which balls are glass and which aren’t—what matters, and what honestly doesn’t—so that when you do have to let one go, you know which one(s) can drop and bounce back. 

Now, go juggle your heart out. 

Never Forget Where You Came From.

There’s a popular quote that goes something like this:

"It doesn’t matter where you came from; it matters where you’re going."

I’m calling bullshit.

This original quote was likely intended to empower people to take control of their future and not suffer from victim mentality about their past or personal circumstances. But it’s not great advice because it suppresses a very important reality: 

Where we came form is extremely important. 

It impacts who we are, how we think, what we believe, how we interact with others, what we think is possible for ourselves, whether we view the world as good or bad, what we strive for. Our history—our upbringing—impacts everything we think and believe and do. 

I’m not about getting stuck on the past. But I am about thoroughly understanding it. 

I decided to take a trip home to NYC this past week. After a very long several months with lots of change and busyness in countless corners of my life, it felt like exactly what I needed. I came home partially to take several business meetings and cover a conference, but largely to reconnect with old friends and spend quality time with my mom. 

The thing about the startup space—or any space, really—is that it’s easy to get caught up in thinking that whatever you’re working on is the most important thing in the world…that startup life matters more than relationship building or taking care of yourself—physically, emotionally, intellectually, and spiritually.

I started to feel a little caught up—something that I think happens to almost all of us when we’re working on something we’re really, really passionate about and committed to. But it was time to step away for a moment. It was time to take a deep breath and recalibrate my personal goals and my vision for helping to grow and support the startup community at large. 

And coming home gave me the space to do that. 

Here’s the thing:

It’s hard to know where you’re going when you lose sight of where you came from. Your past gives your future wisdom-filled direction. 

When you know who you are and why you do what you do, you can better understand where you want to go, why you want to go there, and how you’re going to get there. 

"Going home," whatever that means for you, is so important. It reminds you of who you are, what motivates you, what your purpose is. It reminds you of that little kid you were—the one who dreamed big, feared little, and enjoyed the simple things in life. It reminds you of what really matters: family, building great friendships and relationships, taking care of yourself, being present. 

Often, when life starts to feel chaotic and you couldn’t imagine taking a few days off, that’s when you need to go home the most—to get back in touch with your roots, take a bunch of deep breaths,  chill the heck out, and recalibrate your sense of what truly matters. 

Entrepreneurship is a tough journey. You will have to do very hard and uncomfortable things in the process of building something spectacular. 

But it is impossible to build anything spectacular when you aren’t taking spectacular care of yourself. It’s unsustainable, and more than that, ineffective. 

Just trust me. I know because I’ve tried to cut every kind of corner with my own health and well-being. 

And that’s the craziest part about it all: when you lose sight of where you came from, you lose sight of where you’re going. 

So, go home. Reconnect. Remember who you are. Put it all in perspective. 

Maybe, like me, that’s exactly what you need.

If You Aren’t Getting What You Want, It’s Probably Because You Don’t Want it Badly Enough.

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Humans have a really strange relationship with failure. 

Even the smallest hint of it terrifies many of us. 

I wish we could all see ourselves as little kids, because little kids are really smart. They really get life in a way that adults just don’t. It’s crazy how we spend the first half (or more) of our lives learning many of the wrong lessons, and the second half trying to unlearn them. 

One of the things little kids truly understand is that fear is stupid. They don’t waste much time being afraid. Sure, there are exceptions. And yes, kids are afraid of things that create physical pain for them—which is totally normal and highly useful no matter the stage of life. 

But, they don’t fear failure. They don’t fear emotional bullshit. They don’t fear things not going exactly as planned. They don’t fear relationships. 

Basically, kids are smarter than adults. 

When we’re really young, we don’t fear much of what we learn to fear. Our natural inclination is to fall, get up, fall, get up again. Our natural inclination is to cry when a friend does something bad to us, and then get over it in, like, 5 minutes. Our natural inclination is to dream BIG and believe those dreams are possible (5-year-olds aspire to be astronauts and NBA players and great teachers and other truly awesome things). 

What we forget as adults is that the walls—the failures—are there for a reason. They are opportunities in disguise…to prove how badly we really want a thing. 

If I’ve learned any one thing this year it’s that life rarely works out the way you think it will. Very rarely. But when you’re willing to take a risk, toss your fear of failure aside, embrace the unknown and uncharted, and get up quickly when you fall (and you will), some truly magical shit starts to happen. 

The size of your reward matches the degree of your propensity to take a risk, get over your own bullshit stories, and break through walls. 

If you want something really badly right now, go get it. Don’t let anyone tell you “no.” I’m serious. 

Because you’re going to get exactly what you’re willing to breakthrough to.

Sounds simple, right? 

That’s because it is. Even your 5-year-old self could tell you this. 

So why aren’t you listening? 

Go chase what you’re after.

 

Are You Spending Your “Free Time” Well?

Yesterday, I wrote about not wasting your time on stuff that doesn’t matter. I wrote:

"Stop wasting your nights and weekends doing things that numb you (like drinking, eating, watching movies, etc.) instead of things that rejuvenate and fill you up.”

One reader left this thoughtful comment on my blog:

"I agree with you that we waste so much time doing things that don’t bring any value, but how can you say that "drinking, eating, watching movies, etc" numb us? What about having fun? Going out for dinner with friends, watching a good movie that will resonate with you or make you feel better?"

I thought it was a great point, so I wanted to write today about what I meant in my initial post. 

You have 168 hours a week. 

If you were to actually look at your schedule and how you spend your time, I think you’d quickly realize 168 actually isn’t a whole lot to do everything you want to do. Free time usually fits into people’s schedules during weekday evenings, but primarily from Friday night to Sunday evening. 

Here’s what typically happens:

You have an overly busy or stressful day at work, so you spontaneously go out drinking or zone out at home by watching a movie or turning on the television. Or, on the weekends, you go out to a long dinner with friends and chat the whole time. Or you go shopping with money you may or may not have. Or you run errands all day. Or you watch more movies and television. 

All of these activities are fine. Sometimes, they are super enjoyable and exactly what we need. My initial point was not that those things are bad—not that eating, drinking, and watching movies are always a total waste of time. 

My point is really that we tend to take our “free time” for granted. When we’re stressed or tired, we often do things that cause us to “zone out.” We drink alcohol (sometimes too much), we eat unhealthy comfort foods (sometimes too much), we watch mind-numbing television or movies. 

I’m not above it—I do all three of the above things from time to time. 

But, it’s important that we start spending more time respecting our free time. 

  • What if what you really need isn’t a glass of wine, but a long run? 
  • What if what you really need is quiet time to journal or read instead of feeling obliged to go to a big dinner and spend a lot of money on Saturday night?
  • What if what you really need is an afternoon to go for a walk with someone you love and step away from your inbox and your smartphone?
  • What if what you really need isn’t comfort food, but the joy of learning to cook a healthy new meal?

It’s not about calling any activity good or bad. The problem is that we too often (from what I’ve observed for years) engage in behaviors that don’t help with what we’re dealing with. They don’t always help us learn or grow. They dont always resolve or rejuvenate. 

The truth is, I know I’m not going to look back on my life 50 years from now and say, “I should’ve drank more often,” or, “I should’ve watched more television or movies,” or, “I wish I had gone shopping more frequently.”

What I’m really going to remember in the end are my beautiful, long morning runs on the Chicago lakefront; spontaneous adventures with a few good friends; the time I spend writing, reflecting, and sharing my thoughts with the world; getting on a plane and exploring somewhere new; and yes, even the occasional bottomless mimosa brunch with someone I love over a highly memorable, intimate conversation.

If those are the memories I know I’ll most savor when I’m looking back on how I spent my life, then I better damn behave accordingly. 

That’s the point. 

Spend your free time however you please. Enjoy the hell out of your free time. 

But think about how you’re going to enjoy it. Switch it up often. Question your assumptions about what it is you really need. Try things outside of your comfort zone. Ask yourself, “Do I want to do X to numb the pain/stress/anxiety/sadness I’m feeling? If so, what substitute idea would actually rejuvenate me instead?”

If the thing you really need is a glass of wine with a good friend, do it. 

If you genuinely want to watch a great television program or documentary, awesome. 

If there’s nothing you’d rather do than go out shopping or drinking with a big group of people, go. 

But make sure what you’re doing is really what you want to do. 

Your time here is limited. Spend the free time you’ve got now on things that will make you feel more free. Do things that actually reflect what you think you’ll most remember and be glad you did down the road. 

Unlike other things, like money or energy, time is a resource you cannot get back. Once you spend it, it’s not coming around again. 

So, spend time doing stuff that fulfills you—not stuff that just numbs you. 

You’ll be really glad you did. 

Your Time is Limited. Stop Wasting It.

The idea that “time is limited” is commonplace. We hear it and say it all the time. 

But, something interesting happens in the day-to-day of life. We forget the weight of that sentiment. We start taking things for granted. We start wasting time. And then we complain about how much of a waste of time those things feel like. Because a lot of what we do actually is a waste of time. 

It needs to stop- because it’s true: your time here is limited.

Most of us don’t have enough years of life to accomplish everything we want to do. So if time is so limited, we need to be maximizing it literally every day. 

It’s time to stop doing shit that doesn’t create value for you and/or others. 

Stop with so much social media. Stop with so much reading sensational news. Stop getting lost on BuzzFeed or Pinterest. Stop watching TV. Stop doing things the hard and long way. Stop wasting your nights and weekends doing things that numb you (like drinking, eating, watching movies, etc.) instead of things that rejuvenate and fill you up. 

If you want to live an incredibly full life that you won’t regret, start changing how you’re spending your time. Do more of the things that generate the greatest return with the smallest amount of time and/or effort. Do things that restore you and help you grow. Do things that restore and help others grow. 

Take ownership of the time you have now. Because it’s limited.

And it’s time to stop wasting it. 

You’re a Genius. But You’ll Never Know Why If You’re Measuring the Wrong Things.

It always hurts my heart when I hear people say they don’t think they’re good enough.

I can empathize with the feeling—when I was younger, I struggled with low self-confidence (I think this is a common experience for pretty much every teenager out there). Even today, though, I have moments when irrational or negative thoughts creep their way into my personal story about who I am, how others see me, and what I’m capable of. I have to literally shake myself out of my own bullshit story sometimes.

But, as I think back to my past year, I’m struck by how radical the change in me has been. A year-and-a-half ago, I was working at a corporate job doing what I’d consider mediocre work, quite honestly. From first grade all the way up through college graduation, I remember being insanely driven. I was totally that girl who sat in the front of every classroom, had a habit of taking on more extracurricular activities than I could sanely handle, and was not satisfied if I got an A- on a test. 

I know…I know.

Luckily, I’ve eased up a bit since then, but the intense drive is still in me and stronger than ever. Not surprisingly, I asked my mom (the person in the world who knows me best) what one word she’d use to describe me, and she said—you guessed itdriven. 

What most people wouldn’t guess, though, is that for about 2 years, I lost a lot of my motivation. I lost that natural zest I’d always had for learning—that insatiable curiosity and bottomless supply of gratitude that makes me who I am, and proudly so. 

I didn’t realize it at the time, but looking back, I can attribute the gradual loss of drive to several things:

  1. Lack of  alignment with my core passions and skills.
  2. In an environment (work and personal) that stifled my growth.
  3. My metrics of success (job title, grades at Columbia University, salary, recognition at work, number of pounds lost) were not the right metrics for me. My metrics should have been: level of job happiness, propensity for smart risk taking, recalibrating my mindset about healthy eating and exercise, and creative latitude. The bigger picture problem was that I was doing work that didn’t make me feel on fire.
  4. Bullshit personal stories. In other words, convincing my own self of stories that were not serving me about: who I was, the kind of work I was capable of, and what was possible for my future.

It’s amazing how different things are now. I have so much to learn and a lot more to optimize, but I’m so excited for the journey. Some days, I feel exhausted from the hustle of startup life—but in general, I’ve never felt more alive and motivated by the stuff I get to create.

That’s what happens when you feel like your work and life are driven by a deeper purpose. That’s what happens when you operate daily at the intersection of your passion and talent. 

I tell you this story to illustrate that change is possible. In fact, it’s inevitable—but you have to be the one who says so. Nothing will change if you don’t change. So, if you want something to be different, you need to do something different. 

It’s a very simple formula. 

The problem is, the average piece of advice just doesn’t work, because the process of learning and growing is so intensely personal. Of course, there are psychological behavior techniques to nudge you into certain thought processes, habits, or outcomes.

For instance, a lot of people say you need to make small changes at a time. That advice works for me when it comes to habit change, like eating healthier or going to bed earlier—but not when it comes to other areas of my life, like changing my personal story or finding the best environment for my growth.

When it comes to changing my personal story, the growth tactic that has worked best is “fake it until you become it.” Basically, telling myself a different, more positive story so often and convincingly that it just becomes my personal truth after a while. That may sound manipulative, but only if you don’t understand that everything you believe is literally a figment of your imagination, and if you want to believe something else, it’s as easy as changing your internal dialogue. 

When it comes to finding the best environment for my growth, the tactic that works for me is making decisions quickly, but affirmatively. For instance, when I finally got the courage to leave my corporate job, which felt like the wrong fit for a long time, I did not hesitate. I figured out a plan and got it done as fast as possible. The same thing with moving to Chicago. I didn’t have a plan—just a very, very strong gut feeling I needed to move here. The moment you have the strength to make something different in an instant, take the chance. Just like standing on a diving board, it only gets harder to leap the longer you wait.

So, no one strategy works for everyone. Even for one person, you may need different strategies to tackle different areas of your life. 

If you’re feeling down about the quality of work you’re doing or life you’re leading, please don’t give up. I get it. I’ve been there. I know it sucks. 

But I promise you it will get better. 

The most important thing is to develop an excitement about the art of testing everything in your life, and never giving up until you see the change in yourself and what you produce that you want to see. 

Because the truth is, there is genius in you, whether you know it or not yet. 

You just need to be measuring your genius against the right thing. 

It’s the scary choices that end up being the most worthwhile.

We are all afraid of something. Most of us are afraid of many things. 

I’m willing to bet that one of the main differences between you and the person you most admire and aspire to be more like is this: 

That person has a different relationship with fear. 

One of the most attractive qualities in any human being is that sense of owning fear. Not ignoring it, not running away from it, not trying to surpress it. Just owning it. 

Think about it. Write down a list of the people you admire. 

They are all a little ballsy, aren’t they? Not necessarily in a loud or ostentatious way. Sometimes, they are quiet and calm. But there’s this presence about them—this feeling that they look fear straight in the eyes every day and say, “I acknowledge you, thank you for trying to keep me safe. I’m going to move past you, so you can be quiet now.”

There is this confidence about getting through totally hard—sometimes terrifying—decisions. 

Because the people we most admire know what many of us suspect: that the scariest choices tend to be the most worthwhile. 

I’m not talking STUPID scary types of things that would put your life or the lives of others in danger. I’m talking about the decisions that feel very right, but also scary, because they go so against our natural self preservation or comfort instincts. 

If you can re-work your relationship with fear—if you can have a healthy respect for it, while still remaining the one who channels your fears versus having your fears channel you—you’ll find it a lot easier to overcome them and get to the really good stuff. 

Here’s the fear process for the average person:

  1. Feel a fear
  2. May or may not consciously recognize the fear
  3. Ruminate about the fear
  4. Ask for advice from too many people about the fear
  5. Try to avoid the fear when you don’t come to an easy conclusion
  6. Take too long to make a decision about the fear
  7. Decide not to do the scary thing that you deeply suspect is also the right thing
  8. Stay the same and never truly progress

Here’s the fear process for top performers:

  1. Feel a fear
  2. Sit with the fear and take time to understand what’s behind it
  3. Ask one or two trusted people about the hard decision related to the fear
  4. Spend a little more time reflecting on the fear, and then based on a combination of head, heart, and gut, make a decision about how to conquer the fear
  5. Conquer the fear using a variety of techniques, including: quick action, positive psychology, simple strategic planning, long-term fear-busting habit formation, feeling the fear and moving past it anyway, taking power away from the emotion of fear itself. 
  6. Take on the next scary choice to further strengthen a positive relationship with fear. 
  7. Wash, rinse, repeat. 

Different, right? 

So, what scary choice that you know is right are you fearing now? 

What decision really resonates with you? What decision would you make if you had no fear?

That’s the decision you should make. You already know it—follow your gut. Because deep down you know it’s the scary choices that end up being the most worthwhile. 

Go do the thing that’s going to be the most worthwhile—no matter how scary. 

Make Something Awesome Happen. You’re Ready Right Now.

 

I often wonder what the world would look like if we spent less time in thinking or planning mode, and more time making stuff we really want to do actually happen. 

On a personal level, I wonder how much more proud of myself and the life I lead if I spent less time worrying or preparing, and more time doing.

I think I’d be more joyful and more accomplished, in both the short- and long-term. So that’s what I’m going to do…ACT more, over-think less. 

What are you over-thinking, over-worrying about, or over-planning for right now? What would it look like if you just DID that thing without worrying about “getting your ducks in a row”?

I challenge you to ship before you’re ready. 

Because the truth is, you’re ready. 

We all are. 

So let’s not wait anymore. Let’s go make something awesome happen. 

You Get What You Have the Courage to Learn

Most of us don’t ask for what we want.

It’s not because we don’t know that we should—it’s because we’re afraid. Afraid of rejection, of hearing “no,” of not being worthy of asking for something we truly want in the first place.

The sentiments behind these popular quotes about courage are common: 

  • "Courage is not the absence of fear, but the overcoming of it." 
  • "Be the change you wish to see in the world."
  • "Leap, and the net will appear."
  • "All our dreams can come true if we have the courage to pursue them."

Well, duh. 

We all know it’s important to be courageous. To pursue our dreams. To create the kind of world we want to live in. To just leap and trust that it’ll all work out. 

But it’s not that simple, right? 

It’s not that simple because we create a very complicated formula in our heads about how success works. In fact, we’ve made it so complicated that you could walk into the nearest bookstore and find thousands of pages in the business and self-help sections on what it takes to be successful. We could literally never read all of the content on the web that provides some form of advice on how to be successful.

We go to conferences, read books, ingest articles, listen to podcasts…all hoping to stumble upon some magic bullet that will tell us how we can make our dreams real. 

And what we forget, at the end of the day, is that achieving that highly sought after feeling of “success” is extremely simple. 

It’s simple because success is more about personal growth than it is about reaching some large, distant end goal.

"Success" is a feeling we get when we land a huge investment opportunity, or finish our first marathon, or make our first $1 million—sure. But, that feeling doesn’t last much longer than the feeling of: getting positive feedback from a client, or finishing an invigorating 10-mile training run, or closing our first small sale, or getting to the ever-elusive Inbox Zero, or having a great conversation with a dear friend, or meeting a stranger you have a deep and immediate connection with. 

You see, we’re not after some destination of final success down a long, yellow brick road. What we really live for are those small wins—those small moments of unexpected joy and gratitude and growth along the way. 

Maybe our responsibility isn’t just asking for what we want, but having the courage to grow from the outcome of asking for something we want—whatever that may be. 

It is true: you get in life what you have the courage to ask for. 

But the truly successful people? 

They get in life what they have the courage to learn, regardless of the outcome. 

And when you begin to think about courage that way, asking for what you want doesn’t seem so scary at all. It just seems like a natural and exciting part of growing and learning.

The most courageous stuff you’ll do in your life happens in the middle of it—not at the end. 

So, what will you courageously learn next?