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Are you in love with your problem?

A few months ago, I found myself in a room with Seth Godin and a small group of eager entrepreneurs. Seth posed the following question:

 “Are you so in love with your problem you’re unwilling to try an imperfect solution?”

This prompted me to wonder how many situations I’ve refused to relinquish control, choosing instead to hold out for that perfect, golden answer that would fix everything in one fell swoop. This refuse to settle mantra has gotten in my way and prevented me from taking steps concrete steps of action.
I know I’m not the only one.
Looking around the room that day, every attendee had scrawled their own dilemmas onto scraps of paper. It may come as no surprise that every one of these problems had a solution that another attendee could devise. It wasn’t that any of these attendees were unexperienced, unintelligent, or unmotivated. Quite the opposite.

It can be easier to hold onto a problem than attempt a resolution that might fail.

We come up with hundreds of reasons why we shouldn’t or can’t, so we don’t. We develop relationships with the problem itself, telling ourselves stories that may or may not be true. We believe our inner dialogue (“It just can’t be done.”), electing inaction over failure and fear. Only the very best for our problems, nothing less!
Of course, we’re able to consider another’s issue with relative calm. As outsiders, we lack the emotional connection and historical weight that the owner carries. We use our own fresh eyes to create probable solutions with creativity and ease, even wondering what the fuss was about in the first place.
Then we arrive at our own obstacles (or put them off for as long as possible), and we’re stuck.
I’d like to ask you the same:

Are you willing to try something that might not work?

20 questions to ask as you enter a new year

They work best if you’re honest:

  1. Am I holding onto any beliefs that aren’t serving me?
  2. What do I want to learn this year?
  3. Have I set any long-term goals?
  4. Are my daily decisions setting me up for success?
  5. Do my present priorities accurately reflect my innermost dreams and desires?
  6. Is my work fulfilling my creative desires?
  7. Am I creating time to pursue outside interests?
  8. Do I regularly allow myself to dream?
  9. Is there a specific topic I can learn more about that will help advance my career?
  10. Have I surrounded myself with people who can help me achieve my goals (and encourage me to get there)?
  11. Are my personal relationships fulfilling?
  12. How do I want to be introduced when meeting strangers?
  13. Do I take an active interest in my health?
  14. How can I regularly create a supportive, positive environment for myself?
  15. What lessons have I learned from past failures and mistakes?
  16. What decisions have I made that that support my belief in my own aptitude?
  17. Do I believe that I have art/work/products that will benefit the world?
  18. Am I becoming more of the person I hope to be?
  19. What is preventing me from change?
  20. How can I start today?

an entrepreneur’s two sided coin

Nothing — criminals, graduate school, Social Media Week, Seth Godin — prepared me for what it takes to be an entrepreneur.

There are many warm, idealistic perceptions of the life of an entrepreneur. Being your own boss, running your own show, creating things that matter, following your bliss. Anyone who has groveled at a desk job is lying if they say they haven’t dreamed of what it would be like to play by a different set of rules. Fantasies of setting your own schedule and having more dimes in your pockets seem anything but illicit.

And the success stories! It’s thrilling to hear about the one who struck it rich, the single mother whose idea took off, the underdog whose product went viral, the family man who sold his company to pursue his passion. We love them. We try to find where they drink. We scour articles and books instructing us how to live passionately and make money while doing it.

Very rarely do we hear about the shitty parts of the process.

If we do, it’s after the big win (and even then, we tend to gloss over those not-so-appealing details). The long hours, the misdirection, the insecurities, the unknown, the uncertainties, the sacrifices, the pain, the anxieties, the waffling bank account. The struggle isn’t what we want to buy. We want the finished product. The clean, packaged version. We shy away from the gritty, dirty parts, and when they happen to us, we’re not sure if we’re on track.

Moments of rolling around on the floor is exactly what is needed for ideas to manifest.

It’s those moments of doubt and despair that prompt action. And it is such moments that make us human, vulnerable, approachable, relatable. Because of these unglamorous, unspoken phases, we champion the entrepreneur. We marvel at their guts, their innovation, their creativity, and their gumption. We should consider celebrating the failures, too.

No experience mimics that initial jump into the unknown and the subsequent thrashing that occurs.

I remember the way my heart would race as I entered the county jail to conduct interviews. I’ve known long work weeks, late nights, early mornings, and the loss of self to put on a good show. I’ve felt the pressure of “that one shot,” that chance of doing something really great, and the pressure of not fucking it up. And I felt the flip side of when it did go well, the postpartum that can follow. I’ve shipped and failed then shipped something else and waited to see what happens.

It’s testing. There’s no guidebook, no rules, no one tells you what to do or what needs to happen.

Nothing will properly prepare you. You don’t need a certain degree, specific experience, or a different title. The project is yours, and it’s waiting for you to give it life. There is no known. There is only doing. And today.

You may never be ready. You might try and realize it’s not for you. But you’ll never learn if you don’t at least try. You must learn through action.

So go and test. Test, and test again.

Get lost or change

When was the last time you scared yourself?

Last week I found myself scrambling up rocks, free climbing what I thought was the summit of Longs Peak. After several hours of hiking, circumnavigating ice patches, carefully placing my feet, holding onto rock slabs, and searching for trail markers, I came to the edge of a very, very steep cliff. Heights don’t usually bother me, but this was something else. Visions of misplaced steps filled my mind, and wind whipped my matted hair.

Across this dramatic divide, there was another peak. Clusters of camera flashes sparkled in clear view. Surely, these people were having a much better time than I was. They were on the actual summit. Me? I had no idea.

I began my epic trek at 4AM to get where those people were. I clearly missed the right path. On the way up, I was comforted by headlamps that flickered in front and behind me. I hadn’t seen another climber in hours. I was pissed. And scared.

I spent a few moments trying to collect myself, talking myself into rational thoughts, eventually reaching the conclusion I needed to make my way back down.

Regression is dangerous.

Footing slipped away beneath my feet, and I was reminded of the whizzing sound a small boulder made on my way up. I was paralyzed.

I didn’t do what I had set out to do, and I didn’t want to quit. This is sometimes referred to as “summit fever.” I tried to snap out of it and focus on the down-climb, picking out some semblance of a trail that would transport me safely to the bottom. My partner pointed out the piles of rockslides that surrounded us. I was ferociously sour, and irrational thoughts began to swoon in my mind.

Why the hell did I get myself into this mess? Who does this? I’ve turned into a city slicker and have lost all sense of self. I swore I’d never climb another mountain again, much less go on any hike over three hours. Tears of anger and frustration and god-knows-what-else leaked from my eyes.

When we test our limits, we have to work harder to maintain perspective.

In the moments we’re tired, scared, overworked, and anxious, a record we have no intention of playing can fill the empty spaces of our minds. It tries to convince us of the poor choices we’ve made and the even worse choices we’ll make soon enough. It lulls us into talking ourselves off the ledge of risk and stay on the safest ground possible — the trail everyone else walks on, the stories everyone else shares, the familiar. We forget to widen our gaze and consider the big picture. As a result, our world shrinks, and with it, the possibility of seeing what lies beyond fear’s foggy lens.

“You made it up. You can make it down,” I chanted over and over in my mind. My steps were gingerly, but I moved in the direction of home. When I reached ground that was relatively stable, I finally saw signs of other life. Footprints carved the dirt, and a group of fellow adventurous appearance in the distance.

“Which route did you do?” asked one member of the stock-photo worthy cohort. I suddenly felt self-conscious as I explained, “Tried to reach the summit, but found myself at the top of a pretty big cliff looking over at it, instead.”

The group widened their beautiful eyes. “That’s a much harder climb than the Keyhole Route, and you probably didn’t see another soul. The view must be incredible!”

Narrow focus causes us to miss opportunity.

“Yeah, I didn’t see anyone,” I muttered. I was too focused on my failed attempt to appreciate the view. “That’s so wicked!” chirped the outdoor model. “You did a way harder route.”

I forced a smile and grunted out a few words of gratitude before continuing on. Whether it was the altitude or the early morning hour, I evidently took the wrong turn.  As I continued walking on a now manageable trail, I mulled over their words. Harder. More scenic. Less traffic. Less traveled. Adventurous.

My spirits slowly lifted. It wasn’t until the next day (after I nursed my crushed ego with good Italian food and set my knees to ice), I realized I had a pretty good story.

Great tales are often unplanned. 

What had gone very, very wrong was now a story of risk and adventure. I had something I could share with (and laugh at) with friends. And with it, I was reminded of two valuable lessons:

1. Getting lost is where excitement happens. 

The moment things go wrong is the moment you learn where your edges are, and you are gifted with the opportunity to push past them.  When you veer off-course, you discover surprises and sights you most likely would have missed if you went “the right way.” That, and you’ll come out with a better story to tell.

2. Your perspective determines the outcome.

It’s easy to forget the power of perspective. We have the ability to choose how we consider situations. If we label an experience as negative in our minds, we miss the opportunity to find the lessons to be learned. A simple shift in perspective can separate the meaningful from the mundane.

Get lost or change your perspective. You might be surprised at how very little effort is required for the rewards you’ll take away.

10 things entrepreneurs [should] know

I’ve learned some tough lessons during my transition into the business world. I’m sharing a few of them here and believe they can be applied to more than entrepreneurial endeavors.

I hope they are as valuable for you as they have been for me:

  1. You’re never finished. There’s always more to be done. Bigger plans, more emails, another phone call, scheduled meetings, surprise encounters…
  2. You have to set boundaries. For yourself, your relationships, your time, your values, your abilities, your email checking. Prioritize, identify what is important to you, and rank your daily to-do list.
  3. Everyone has an opinion. That doesn’t mean you have to take their advice. Listen, and take what works for you.
  4. You’ll be scared and nervous and anxious as hell. Starting is scary. It doesn’t go away, but it gets better.
  5. You will fail. And you’ll fail hard. You’ll really f— something up, but you’ll learn from it and you’ll change it for next time.
  6. Not every idea is a slam dunk. That’s OK.
  7. Celebrate the wins. Even the really small ones. If you don’t recognize where you’re going and how far you’ve come, you won’t want to keep moving forward.
  8. It’s OK to ask for help. It’s impossible to know all there is to know about everything that is involved with running a business. Find people who can help and don’t be afraid to admit ignorance.
  9. It’s a process. You learn to ride the tide. Sometimes it’s in your favor, other times you’re swimming in the ocean for what seems like forever. There will be another wave, you’ll get to the shore, and then you can swim back out and do it all over again.
  10. It’s OK. It’s going to be OK. You’re OK. What you don’t know is OK. What people think of you is OK. Be OK with yourself.

How do you see risk?

Everyone experiences risk. No one is immune to the anxiety that comes with it.
The difference between the daring and the successful is that they’ve learned to cope with it.
Questions to ask:
How can I minimize my anxieties surrounding this?
Can I make myself feel better about this decision?
The more you dive, the more you’ll enter the water in a way that doesn’t hurt, and the board won’t seem quite as high…
Jump.