Optimizing Your Career for Income is Like a Dog Chasing His Tail

Meet Doug.

Doug is a good boy. Some have even called him the best of all the good boys. But that was a long, long time ago.

By all accounts, Doug was no ordinary show dog. He didn’t come from a champion pedigree. He didn’t have the best coat, nor the best markings.

But Doug had something few other dogs are born with: a willingness to work harder than any other dog.

Doug had never seen a show ring, let alone win a prize. But that all changed when Master rescued him.

The Master took Doug under his wing. He gave him a nice house. He fed him good food. But most importantly of all – the Master recognized Doug’s potential and he treated him with respect.

The Master told Doug stories about legendary show dogs – how they bounded across the arenas with grace and how they lifted the spirits of crowds.

Doug wanted nothing more than to be a champion someday, so he could inspire crowds. The Master warned Doug how hard he would have to work – still it did not deter him.

So the Master agreed to train that ordinary rescue pup into a champion show dog.

Doug’s work ethic served him well. When the Master said sit, Doug sat, and the Master rewarded him with a treat. When the Master said lay down, Doug laid, and he received a treat.

Occasionally, Doug would encounter an obstacle that didn’t come naturally – there were no treats for bad performance.

Still, the Master patiently instructed him through drills to improve his footwork – so Doug worked harder and harder until he got it.

After several months, Doug and the Master entered some contests. Doug performed well and earned third prize, but not well enough to win. Doug still had much to learn.

Master warned Doug they would need to work harder yet to win – but if Doug wanted to quit, they could. Doug refused. He said he wanted to become a champion.

So they continued to train.

Several months and contests later, Doug had developed quite the reputation for himself. He had taken home several modest winnings. But his attitude began to change. Doug became prideful.

Doug began to forget why he wanted to be a show dog. He liked the level of success he had attained, and he forgot about hard work. No longer did he dream of glory – instead he dreamed only of more and more treats.

One day, Doug confronted the Master. Doug demanded more treats. Doug warned the Master, if he didn’t pay up, he would find a new Master.

The Master didn’t want Doug to leave. But he didn’t want Doug to miss out on his potential, either. So he told Doug a hard truth…He told Doug the only way to get more treats was to win more.

But Doug refused to hear it. So Doug left the Master who had trained him behind and set out to find a new one.

And a new Master he found. The new Master gave Doug all the treats he wanted. He showered Doug with a regular treat allowance and bonus treats – even if Doug didn’t train. After a few months, Doug gave up training all together.

Then one day Doug woke up. He realized he had gotten fat. It had been years since he competed in a contest…and he felt empty. He had forgotten how to bound across the arena and longed for the applause of a crowd.

He even missed the old Master. The treats had made him too comfortable, and distracted him from his goal…

But now, Doug realized, he was too old to compete. He had missed his chance at glory…all for a few extra treats…

…

I was once Doug. I set out with high hopes and good intentions. Then I got distracted by money.

It made me forget all the people who helped push me to become better. But it was an easy way to keep score, so I chased it.

Until one day I realized that doing the kind of work that makes me happy is worth more than all the treats…

May you discover the same before it’s too late.

*I originally published this post on Quora in response to the question What career limiting moves have you seen people make?

A Master

Tiger Woods won his 5th Master’s tournament today.

Even for a golf outsider like me, it’s clear he carries something different into his game than most other golfers.

He doesn’t smile. Tiger’s intensely focused. He doesn’t laugh off missed shots.

Then, in the final moments, once he’s sealed the deal – only then does he celebrate. Still, his celebration matches the level of his intensity. It’s a fierce outburst. Of having put himself to the test and risen to the challenge.

Love him or hate him, the dude has style – and we just witnessed a one of the most legendary comeback stories of all time.

Congrats, Tiger.

You Can Walk Away

I got my first real job at age 16 – bagging groceries at the local supermarket.

The experience taught me a lot about business and how to work.

Lessons like:

  • How easy it is to stand out among peers just by working hard.
  • How attitude about work is a personal choice.
  • How decisions are made about which items go where and why.
  • How a customer’s journey impacts their buying behavior.

But the very last lesson I learned proved to be the most important.

I graduated to stocking shelves several months in. I loved it. Walking up and down a perfectly-faced aisle brought me untold joy. I gained responsibility fast.

Until one day a manager issued a strange request. He asked me to peel date labels off an entire shelf of expired items, then put them back.

This posed my first real ethical dilemma: Should I do what I’m told or what I think is right?

I chose wrong. Afraid of performing poorly at my job, I peeled the labels off.

The decision haunted me the rest of my shift.

So I went back. I took down every item and threw it away.

Then I quit. But I never forgot.

The situation taught me why I should trust my conscience and take ownership of my actions.

It’s easy to become complicit when you blame someone else’s judgment. Don’t give away your power.

It takes courage, but you always have a choice. You can walk away.

*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!

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?

 

 

When To Walk Away

I spent two hours at a car dealership this morning.

Before I left the manager asked me about my experience.

“Honestly, this is taking longer than I’d like,” I replied. He acted shocked.

“Really? Usually people are here for 4-5 hours, you’ve only been here for two!” he replied.

It reminded me of something I often take for granted: the freedom to walk away.

So I exercised it.

Maybe it’s easier to see this freedom on display when it involves a pricey transaction. But we carry the same freedom into nearly every arena of life.

It’s Always an Option

Hate your job? You don’t have to stay.

Toxic relationship? Call it off.

Don’t like where you live? Move somewhere else.

It’s easy to forget we have this power. Especially when other parties benefit. They’d have us believe we’re powerless. That we have to be confined to our current circumstances.

Exercise Your Freedom

We have the freedom to walk away when things don’t satisfy our needs or interests.

It’s a super power. But only if you exercise it.

When is the last time you walked away?

 

 

 

Let’s Shake On It

I grew up in a place where handshakes mattered. Where a man’s word was his bond.

Call me old fashioned but the same principle still governs my worldview.

Doing business shouldn’t require contracts.

Except today, you’re probably making a stupid decision if you’re not getting something in writing.

Sure, contracts make things easier in some ways. Contracts define the scope of expectations for both parties. They provide a means for recourse if terms aren’t met. These legal instruments hedge against untrustworthy behaviors.

But contracts also create business friction. They introduce a third-party (lawyers) into a situation that could otherwise be settled between two competent, consenting parties. Contracts extend the sales cycle. They create a barrier to satisfying two party’s unmet needs.

Incentives matter.

People respond to incentives. Where there’s a big enough incentive, there’s also a temptation to violate an agreement. Sure, contracts provide an avenue for reconciliation in these cases – but at what cost? (Read: more lawyers).

Skin in the Game

As Robert Frost said, “Good fences make good neighbors.” In some sense, contracts are one way for a person to up the ante on someone else’s behavior. They add a little skin in the game for both parties.

Absent a contract, what’s the worst that could happen? Maybe it’s a line of thinking that ruining your reputation isn’t that high a cost. That with the right amount of money you can buy a new reputation – or better yet, buy the victim’s silence.

Kinda shady, right?

The Future

Blockchain holds a lot of cool possibilities for getting us closer to “handshake” agreements again. Not in the sense that everybody suddenly begins acting out of good faith. Rather, it takes everyone as they are. Hey, let’s just pretend everyone’s a shady motherfucker. Instead, imagine a world where people don’t have to trust one another to do business.

That’s not to say that blockchain will eliminate the need for trust. But what if it could minimize the need for trust? What if two parties could engage in transactions that didn’t require egregious legal fees, lengthy due-diligence, and an arthritic-inflicting pile of paperwork?

What if a handshake created an actual binding, digital contract? Instead of needing to “insult someone’s honor” or demand a contract – imagine if contracts generated spontaneously.

Pretty wild to think about, right? Maybe not.

Nice guys finish last.

Sadly, I don’t think honoring handshake deals is back on the rise. But the cost of transacting business AND providing means for enforcement is getting a lot easier.

I like to imagine a world where, instead of looking over your shoulder or worrying who’s going to screw you, you can confidently go about your business in good faith.

Maybe there’s still hope for the nice guys out there after all. But for everybody else, get it in writing.

 

 

 

 

 

 

 

 

Don’t Wear Your Beer Shirt to Church

I’ve long since abandoned the atheist phase of my early 20s. But I haven’t gone to church regularly in nearly a decade.

After spending an ungodly portion of my youth engaged in church activities, I walked out.

They were wrong.

I had a serious disagreement with church leadership as a teen. Their argument felt more contrived than actual verbal confirmation from God: we prayed over this and it’s what God wants.

I felt like I was being looked down upon because I was young. So when my pleas fell on deaf ears, I decided to boycott.

I was wrong.

I struggled reconciling this incident for years, searching long and hard for answers. Then I realized my spiritual journey has nothing to do with the way other people behave. It’s entirely personal, and my misgivings with people need not interfere with my own pursuit for truth.

Something’s missing.

Yet I can’t help but carry some burden of the weight I’ve felt in almost every church setting I’ve tried to reengage. It hasn’t felt like something personal. Nor has it felt up to the snuff on the message it markets.

Maybe it’s the unruly pagan in me speaking, but church and organized religion have always felt more like institutions of people-judgment than of people-development.

I don’t mean people who go to church are bad. On the contrary, many of the best people I know – including my dad – practice what they preach as adamantly as anyone. But my own experience has left me wanting more than what I’ve found any church to offer.

I try to recreate the experiences I enjoy.

I find many of the concepts embedded in church culture appealing. The fellowship, pursuit of truth, worship, prayer, devotion, discipleship, not to mention a good potluck..

But my experiences with these activities as part of a church have always felt tainted. Almost as if they were guided more by ulterior motives than to drive personal growth. Like a need to validate certain interpretations of scripture or someone’s ego.

I’ve found my own pursuit of all these things to be much richer when done in a decentralized setting, not under the watchful governance of liturgy.

Come just as you are.

A lot of ideas I have don’t make for polite Sunday-lunch conversation. Still, many of them are both informed and inspired by scripture, theology, and Christian philosophy. One such idea I’ve taken from a classic hymn – that we should come just as we are.

Every major intellectual or spiritual leap I’ve taken has been predicated on this notion. The freedom to approach ideas just as I am has led me through more personal discovery than all learning involving an intermediary combined.

This approach to learning, truth, and spiritual growth makes me feel like I have some say over it. That if I’m not satisfied with the growth I’ve achieved, I can dedicate more energy to it. Or if I’ve fallen out of step, then it’s my responsibility to recover – not some institution’s responsibility to shepherd me.

I own my spiritual growth.

I don’t think it’s some religious figure’s or organization’s place to cast stones on the route I take in my spiritual journey. If church or religion should have any part in my spiritual endeavor, then it should be as secondary influences, not as some spiritual auditor I’m trying to impress to earn a credential for heaven.

Taking ownership of my spiritual development has freed me to seek truth on my own terms, at my own pace – even if that’s meant making a lot of mistakes.

No, I don’t hate church. But my congregation wears the same clothes 7 days a week.

Don’t Confuse Motion for Progress

It can be easy to confuse motion with progress. But the two are not the same.

Progress requires direction.

Motion, on the other hand, does not. Absent a direction, motion is nothing more than aimless movement.

Movement for movement’s sake, does not mean you’re making progress. You can see this distinction clearly in the perpetually busy, but broke person. They’re always short on time and cash, but never getting closer to their end goal. They’re not making progress. They’re aimlessly moving.

Contrast this with a person of high progress. They move judiciously. People of progress don’t spin their tires. They don’t fill their calendars with bullshit coffee appointments, and they don’t waste money on things they don’t need.

People of progress deliberately chart courses toward their goal. Then execute the path. They view and behave much like someone charting course for a cross-country road trip. With a destination in mind, they carefully determine the best routes, the best rest stops, the right driving playlist, and assess the time it will take.

Motion negates this type of planning. Motion is not about moving toward a goal. It’s about moving. This does not make it worthless. Motion certainly has a value – consider the art of dancing. There may not be a goal beyond getting lost in the dance. In this sense, moving becomes the goal. In this rite, motion showcases its value best.

At face value, motion should not be confused with progress. Motion is about moving. But progress is about moving somewhere.

 

 

 

They’re All Super Markets

There is no better argument for deregulation than marketplaces.

If you haven’t experienced one, I recommend it.

Ebay, Uber, Lyft, Amazon, Rover, Facebook Marketplace, the list goes on.

Anytime buyers and a sellers congregate together something beautiful happens. There is a special kind of harmony when the friction of regulation is removed from transactions, and people are set free to deal with each other peacefully.

Even the negotiation process is a form of art. Both buyer and seller have a price point that makes sense to them for a particular good. Neither has to participate if the price doesn’t fit their model. But when both parties finding that happy medium – magic happens.

Markets free people people to signal their preferences with the world: “I have X good at Y price, who wants it?” and “I have X budget, and am looking for Y good, who’s willing to sell?” Both parties participate of their own accord. Peacefully.

People often give markets a bad wrap. Protesting low wages for ride share drivers, or Amazon and Ebay as disrupters of the retail industry. But they’re missing the point.

In free marketplaces, no one forces others to participate in exchange. It happens voluntarily. Spontaneously. Beautifully.

This kind of mutually-beneficial exchange forms the bedrock of a free, prosperous, peaceful society.

Markets are an amazing innovation. They’re something to marvel at. Not condemn.