When You Start Juggling Unalike Objects

You’ll drop the ball sometimes. Juggling is hard.

The sooner you embrace it, the sooner you can focus on improving your act.

We all juggle. Some of juggle people. Others juggle responsibilities. Some people juggle identities. Others juggle work and life.

Juggling is easier when everything goes together.

Imagine you’re juggling baseballs, for example. One or two is easy. A third increases the difficulty. A fourth takes some real skill. But what happens when you throw a knife into the mix? Suddenly, an unmatched object confounds the mix. It becomes an entirely new act. One that requires much more deliberate focus.

I’m convinced the same happens in life. Both in the number of different types of things we juggle – and the number of things we juggle that are different from the other things.

Friend groups paint a good picture. Think of all your friends. How many “groups” do the fit into? Are there some you don’t think would mesh well with others?

What about identities? Are you a different person to different people? How many different identities, and to how many different people? Surely it gets more difficult to keep straight the more there are. (The idea of this sounds painfully exhausting.)

The easy way out is to stop juggling. Sure, consolidating or off-loading a few things you’re juggling can help, too. But in both scenarios, you’ll miss out on a lot of the richness of life.

A little variety in life never hurt anyone. You don’t have to have an identical set of friends. Or responsibilities. Or interactions.

Even when the inevitable collision of juggling a lot of different things happens, the drama adds a layer of flair to the story you’re living.

It’s not easy. But doesn’t a life filled with homogenous experiences sound boring?



Lost Momentum Halts Dreams

About a year ago, I went through a pretty dark period.

I got stuck.

I needed help but felt too scared to ask. People like me don’t get help, I told myself.

So I didn’t. And I prolonged my suffering.

Then a friend opened up about a struggle. It shocked me.

I wasn’t alone – I just chose to struggle alone. After that, I decided to ask for help and it set me free.

Maybe you’re going through something. Maybe you’re not. But would anyone know if you were?

I don’t presume to know your situation. I’m no guru. But I do know lost momentum halts dreams.

Big struggle, small struggle – asking for help takes courage.

If you’re stuck, you owe it to yourself to do something about it.

Success will demand the best from you. You can’t offer your best when you’re stuck.

If you feel stuck and don’t know what to do about it, reach out to someone. Or shoot me an email. I can’t promise I know how to help. But I’ll offer my best.

Sometimes all it takes is a little nudge.


*This post originally appeared in my weekly Crash Newsletter earlier today – where I share inspiration, and the week’s best content on careers, personal growth, and how to get ahead. If you’re interest in learning more, sign up here!

Endure the Opposite

In one of my favorite poems, The Prophet, Kahlil Gibran describes the relationship between sorry and joy as proportionate.

He eloquently writes that as our ability to fathom joy expands, our comprehension of joy increases in step.

“The deeper that sorrow carves into your being, the more joy you can contain.”

I think the concept Gibran describes also applies to a great many other diametric opposites.

Take patience as another example. My dad always jokes, “I prayed for patience, so God gave me twins.” Maybe patience came at the cost of endurance over time. Ironically, patience took time.

Henry David Thoreau provides another example: “A man is rich in proportion to the number of things which he can afford to let alone.” In other words, the more a man becomes content without, the more abundantly wealthy he becomes – if even only in spirit.

Perhaps fear and courage are no strangers to this same phenomenon.

Think about the way people learn to express courage. It starts small. Incremental gains lead to larger challenges. For instance, a kid first scared to ride without training wheels soon becomes a kid getting back up after falling off his bike.

The more you fear something, the more you bring it to life. The larger it looms over your head, the more courage facing this fear requires. Yet, the larger fears you approach head on, the more courage you earn – establishing a new “courage baseline.”

These relationships provide an interesting thought experiment about how we should approach our actual desires.

What I’m trying to get at is that maybe striving for more of something, like happiness or wealth, is futile.

Maybe a better approach is to strive for the opposite. And only by knowing the opposite condition can we become more intimately prepared for our actual goal.

Trust the Process.

Imagine walking into a Michelin 3-star restaurant and balking at what the chef puts in front of you.

Absurd, right?

What about going into a doctor’s office and arguing with him about his prognosis?

Or servicing your car at the local mechanic’s shop and disagreeing with his recommendations?

You may not like the price. Hell, you may not enjoy the news. But these people have access to secrets you don’t yet.

They discovered these secrets through years devoted to their trade, their craft. These secrets allow them to tune in to a higher frequency than us in their realm of expertise.

Experts Have a Process

When you embrace something new, seek out someone who knows more than you. They know things you don’t. They can expedite some of your discovery process toward the answers you’re after.

Consider a chef. Maybe you’re after a new culinary experience. He or she is more qualified than you to assist.

Or the doctor. Perhaps he or she can reduce the amount of time you experience discomfort.

Or your mechanic. If you could stretch another 100,000 miles out of your car, that’d be great, right?

Part of an expert’s secret is his or her process. A regimented way of going about their particular craft.

Yes. Sometimes they get it wrong. But the process they use allows them to increase the frequency with which they are correct, and reduce the likelihood of being wrong.

Can you say that about yourself?

Commit To The Experiment

What if you couldn’t change your mind until you allowed things to run their proper course?

I call it committing to the experiment.

If you want to test for something, construct a hypothesis and establish a window for testing. Consider taking a new job, for example.

I hypothesize one year’s time working at Company XYZ will enhance my career mobility, quality of life, and earning potential.

Focus on specific outcomes.

  • How will running this experiment impact my life?
  • What is the expected value or return of a successful experiment?
  • How will I measure success?
  • What am I willing to invest in completing this experiment?

Committing becomes easy when the end goal is both near and under constraints.

The constraints set a clear window of opportunity to satisfy the question you needed answered. These also establish an expiration date to let yourself off the hook.

More importantly, it allows you to quash optionality.

Experiments encounter turbulence. Unaccounted for variables will attempt to trip you up. The fewer you allow to derail you, the better.

Optionality can kill progress.

It’s the voice in your head telling you to turn back. It’s that silent killer asking you, “What’s in this for me?”

By committing to the experiment at the onset, you free yourself from this bondage. Experiments eliminate the cognitive overheard of wondering what else you could be doing.

Give yourself the freedom to run tests uninhibited. Commit to the experiment.

A Key To Better Feedback & Relationships

Everything get easier when you care about other people.

That’s it. That’s the secret.

There’s a lot of cliche-sounding advice in the world about how you should show compassion when you give feedback. And about how managing people is easier when you take an interest in others.

It’s not wrong. But it’s a lesson easier won through experience.

If you want to improve the way you interact with other people, you actually have to care about them. You can’t just pretend.

It’s extremely difficult to construct a thought experiment of “What would someone who cares about this person say?” It’s also easy to see through. Contrast that with actually caring about another human being. You don’t have to play games or wonder what someone would say. You’re already equipped to do it.

This may all sound pretty obvious. But it’s not in practice.

Compassion takes practice.

It takes practice because there are appropriate limits. You can’t just be compassionate. You also need to understand when and how to show restraint.

Kim Scott in her book Radical Candor describes this as ruinous empathy. It’s when you’re too nice to someone. Beyond the point of being honest or helpful. She discusses a better alternative, the namesake, radical candor. Which is about…

Another great book on the topic is Kristen Hadeed’s Permission to Screw Up. She institutes a great approach in her business call FBIs. FBI stands for Feeling, Behavior, and Impact. If you want to practice compassion and get your point across with acting like a complete asshole, communicate the specific behavior, how its makes you feel, and the impact is has on your business or relationship.

But like I said, there’s no better teacher than personal experience.

I think to my own experiences. In romantic relationships. In friendships. In professional relationships. As an employee. As a boss.

There were several times in my life when I was much younger where someone I thought was a friend achieved some small amount of success. It made me jealous. I asked myself why and realized we didn’t have much more than a surface level friendship. A little self honestly told me I kept this person around more as someone who motivated me. I didn’t care about the person though. That was a hard truth to swallow.

Contrast that with another friend. Someone who is more like a brother. He had a great job offer on the table and asked me advice. It was easy to give him honest advice, whether it was what he wanted to hear or not. When he landed the job, it was easy to be genuinely excited for him. I valued our friendship. I cared about his success.

I share both examples to show an important contrast.

In the first relationship, everything was transactional. I cared about what that person could offer me. Wrong or not, I didn’t care about the person. In the second, the basis of our friendship was not self-serving. It was about a mutual benefit and enjoyment of being friends. Compassion flowed naturally from it.

The same thing happens in professional relationships, too.

When you’re a manager, it’s easy to get caught up in making sure people “below you” are doing their jobs. But it’s also easy to dehumanize other people when you’re only weighing them by their inputs and outputs. But here’s a secret I’ve learned from observing both great and terrible managers: if you invest in people, they’ll consistently surprise you.

Yes. It sounds cliche. It sounds obvious. But it’s not always.

Sometimes it takes concentrated effort to get past the surface level details. It may mean intentionally being friendlier or trying to become more personable. It may mean you have to become vulnerable and open up.

It’s not always easy. But it’s worth it.

If You Want It, Behave Like It

You can talk the talk, but can you walk the walk?

Almost every time I’ve started something new I came face to face with imposter syndrome. When you first start out it’s easy to believe you’re not good enough.

It’s easy to get distracted by the people in your life who inevitably believe you’re going through a phase and the new thing won’t last. But worse yet, is how easy it is to talk yourself into believing that you’re not good enough or not worthy enough to succeed at your new thing.

It happens to the best of us. But only rookies let the doubts erode their self-confidence and conviction.

The more times you start new things and see them through – even the small things – you’re incrementally practicing self-discipline. Over time it adds up. It’s not exactly easy to start and gain momentum with something new, but a secret is that it gets easier the more you practice it.

In small and big things in your life, your behaviors over time are a better predictor of your outcomes than anything else.

Take writing as an example.

If you say you want to be a writer, for instance, but you’re not regularly writing, chances are there’s a low likelihood you’ll ever actually do it.

On the flip side, if you write every day – even if you don’t have some big idea for publishing yet – the sheer act of exercising your writing muscle will set you up for success.

When you first start out you may not know the proper behaviors to move you closer toward your goal (even if you can’t yet define it). Don’t stress. Just focus on doing one thing each day to move you closer. Anything.

The best way to become something is to start behaving like it.

If Your Friends Call You Crazy, Don’t Sweat It

“I’m not going to law school.”

When I first told a friend what I planned to do, he asked if I needed clinical help.

“I don’t want to wait around,” I said. “I hate sitting in a classroom and I want to start something now.”

Before the words even left my mouth I knew we were on different wavelengths. 

He had just finished his first year at one of the most prestigious law schools in the country. His course was charted already. He was comfortable in it. I wasn’t. I didn’t know what I wanted.

I needed a big challenge and I wanted something that sounded impressive to me. That’s it. 

I felt confident I could scratch those itches cheaper. I hated the idea of amassing a huge debt load in exchange for 3.5 years of suffering in an artificially-lit lecture hall. Even the lucrative salary prospect didn’t bring me comfort. 

I was searching for a solution. It didn’t have to pay big. But it had to be exciting. It had to challenge me. And it had to lead to something I felt worthy of my time and energy.

To be continued…

2016 and counting…

During this time I’ve gained exposure to all the nitty-gritty business of doing business. I’ve also come to recognize the brilliance of people passionate at work to create solutions. I’ve seen the trenches and served on the frontline of what I consider to be a great entrepreneurial endeavor.

I moved 1,200 miles across the country this year, but it hardly captures the ground I’ve made.

I’m a (human) gestation period through a yearlong personal and professional development program. (See Praxis). Since January, I’ve been apprenticing under the Founder & CEO of a tech/accounting startup–which recently closed a $4.2M Series A funding round. (See Ceterus). I’ve experienced unprecedented growth as part of both. It’s been the most difficult, stressful, chaotic, roller coaster ride I’ve ever taken. These have also been the most rewarding, invigorating, fulfilling, and actualizing months of my life.

During this time I’ve gained exposure to all the nitty-gritty business of doing business. I’ve also come to recognize the brilliance of people passionate at work to create solutions. I’ve seen the trenches and served on the frontline of what I consider to be a great entrepreneurial endeavor. I’ve experienced a few victories. And I’ve come to know defeat. I see both as allies for learning now.

I’ve never felt more limber than I have these few months. I’ve never felt more open to possibility.

In the past six months, I’ve:

This is merely a snapshot of the things I’ve been doing. It hardly does justice to all the learning that’s been happening behind the scenes. It’s been an incredible journey so far.

I couldn’t summarize what it’s taken to get here.

There have been many long hours, late nights, and early mornings. There have been whole days where I felt like I was banging my head against the wall. There have been weekends where I didn’t turn the lights on or leave my apartment and stayed glued to the couch, entirely spent. There have been dozens of late-night ice cream and beer errands.

There have also been some of the brightest, happiest, and most hopeful hours of my life. There have been dozens of “Aha!” moments. There have been countless small victories with violent fist pumps and silent cheers.

And there has been an incredible support network beside me through Praxis, my family, co-workers, and friends.

2016 has been monumental already. I look forward to sharing all that precipitates in the coming months as I continue to grow.

As always, thanks for reading.




Stay Hungry.

In the short months that followed I learned just how capable I was. Capable of working hard. Capable of learning. Capable of observing. Capable of improving at least 1% or more each day. Capable of waking up early and working ‘til late. Capable of dedicating myself to labor I believed in and capable of being mentored. I was as capable as I was willing to be.

Six months ago I sat salivating over South Carolina’s tastiest chicken biscuit and an irresistible business opportunity.

I had flown to Charleston to pitch a pretty aggressive business development proposal to my then-boss. My presentation projected 200% growth for his company in 12 months, led entirely by yours truly. It was ballsy. It was unlikely to be accepted. But I believed I could do it and I had to try.

I didn’t know what was going to happen when I took that 1,200-mile flight to a city I’d never visited before to pitch the most aggressive presentation I’d ever crafted to a man I’d never met. But I wasn’t scared. Quite the opposite. I was as alive as I’d ever been.

So when my proposal was rejected I didn’t lose an inch. I gained miles. What I did that day made me proud. It gave me confidence and resolve. It gave me closure. It made what happened next seem natural, providential even.

My experience has given me an acute awareness that failure is part of life. I’ve learned failing usually signals an opportunity to succeed at something else, perhaps even greater. What happened in South Carolina that week did not shock me. It came as no surprise. Not to me. I’ve been working my entire life to position myself for the exact type of situation that unfolded.

What I didn’t know when I got on the plane to leave Oklahoma was that I wasn’t going to South Carolina for this proposal I worked so hard to create. I was following a path years of diligence had carved for me.

It was 24 hours before my proposal and I had taken maybe a bite out of my biscuit. I lost my appetite for food. A new hunger had taken hold of me.

Sitting before me on that table was more than South Carolina’s best breakfast food. There was also opportunity served. The type of opportunity so one-of-a-kind you can’t even dream it up. But for me it was also the kind of opportunity that made me hesitate and ask myself, “Am I capable of this?”

The shellshock wore off with the rejected proposal, and I knew what I had to do. Nothing would stop me. No one would stop me. I knew the only way I could answer that question was to meet it with my best effort. So I did. And everything fell into place.

In the following weeks I uprooted and moved 1,200 miles away. I had no second thoughts. I hadn’t even figured out how I would make it all work when I left. But I found solidarity in the drive. I knew I would make it. I believed I would.

In the short months that followed I learned just how capable I was. Capable of working hard. Capable of learning. Capable of observing. Capable of improving at least 1% or more each day. Capable of waking up early and working ‘til late. Capable of dedicating myself to labor I believed in and capable of being mentored. I was as capable as I was willing to be.

Now I no longer worry if I’m capable. Instead I believe with enough resolve, effort, and willingness to get in the trenches and deliver, I am capable of anything. Anything. And I intend to prove it. Every. Single. Day.

I’ve come a long way since that chicken biscuit, but I’m still as hungry as ever.

Present day, I report directly to the Founder & CEO of a VC-funded startup. No two days have been the same since I started. I’m intellectually stimulated and challenged daily. I get to dive in and solve problems all the time. I get to learn new softwares and help design and implement new processes. I have 360 degrees of exposure to a rapid-growth business that’s taking an $81 billion industry by storm. And I’m only 24 years old.

I could be in law school or working toward an MBA. Instead I experiment daily with actual business operations and with actual entrepreneurs. I could be married and working on a family. Instead, I’m single and creating a fulfilling life. I could have taken a high-paying corporate job, grown roots, and bought a house. Instead, I‘m mortgaging myself so I can be an asset wherever I choose to go, with no cap on income potential. I could be living out any number of prefabricated lifestyle templates. Instead, I’m not. Instead, I’m blazing my own trail and I’m creating a life governed by my own terms.

It all happened because I bet on myself. Not on a credential. Not on conventional wisdom. Not on the status quo. It happened because I refused to follow the beat of someone else’s drum. It happened because I needed to prove to myself what I could do given the chance to thrive. It happened for me and it can happen for anyone who wants to go out and discover the life they’ve always wanted.

Your story to the life you’ve always wanted can begin anywhere, too. Mine started with a chicken biscuit. And that’s why I believe it when people say breakfast is the most important meal of the day.

Stay hungry, my friends.