Category: Careers

Imagine yourself at the bottom of a set of stairs. This is you at the beginning of your career.

Your ideal career scenario stands at the top of the staircase.

For me, it’s the freedom to create a life on my own terms and a reputation strong enough to unlock the opportunities I aspire for.

The stairs represent the challenges and steps you must take to get there.

Each step gets you closer to your goal. Each step unlocks a little more of what you’re after.

The idea of the “company man” – where you work the duration of your professional life at one corporation – has long timed out. Today, the average tenure has dropped significantly – roughly 4.2 years.

The cost of information has dropped significantly, too. Meaning, it’s much easier to discover new opportunities, for companies to learn about you, or for you to start your own business – even if that’s as a freelance service provider.

Leverage

This means you have more leverage today as an individual than your parents or grandparents had.

You’re not beholden to one organization. The more skills you have and the stronger the reputation you have at signaling those skills, the more leverage you have.

Your journey isn’t limited to climbing one corporate ladder. It also means you’re not limited to climbing steps one at a time.

In the world we live in, focus on doing good work and the reputation you build will open opportunities for you.

Many of the best opportunities aren’t things you apply for – but the types of things that allow you to skips steps and get closer to your end goals.

Don’t worry about whether you’re staying at a company too long or moving around too quickly. Instead focus on

• Adding value where you’re at however long you’re there.
• Learning and engaging in meaningful work.
• Refining your option set – by removing or avoiding the kinds of work you hate.
• Documenting your work and learning – by building a digital portfolio or body of work.
• Creating lasting relationships with people who push you to be better.

Your career is a discovery process. Go out and do what you need to do to discover and build a career and life that brings you fulfillment.

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*This post was originally published on Quora in response to the question Is staying at one organization for a long time good or bad for one’s career? Why? It’s received over 110,000 views in the past month.

The lights were off. It’s how I liked to work.

A faint glow from two 27” monitors and a MacBook Pro reflected off my glasses. Beneath my hoodie, the steady mind-numbing pulse of screamo bass outpaced the tap-tap-tapping from my keyboard.

I forgot how long I’d been there. I’d woken up around 4:30 am and I’d be there well until the evening hours.

Half a dozen years into my career, this was a typical day.

At least, until the day I had my first major health scare…

I stacked 80–100 hour work weeks regularly. No one made me. There was no formal “work hours” policy. Success was about results. But in the breakneck pace of a hyper growth company, there is never a shortage of problems or projects to get lost in.

That kind of environment is addicting, dangerous even. There’s an almost pornographic appeal to putting in long hours. Even when you tell yourself you’re having fun – which I was – eventually your faculties erode. The warning voice of conscience “you’re overdoing it” fades the longer you allow workaholism to prevail.

It doesn’t have to be this way. And probably it shouldn’t be. But it’s a picture of what life had become for me.

I ate like sh*t. Burgers. Pizza. Tacos. Fast food.

I rarely exercised anymore. Unless switching from standing to sitting or pacing on calls counts.

Not to mention the excessive intake – coffee to kickstart the day and alcohol to shut the mind off most nights.

Health took a back seat to work – both mental and physical health.

Then one day it went too far.

Not unlike any day, I rose early and slammed several coffees before anyone else made it to the office. But I remember it was a particularly stressful day.

That’s what set it into motion, I told myself: the stress.

It started as a small ache in my side. It slowly intensified through the morning. By 11 am, I was doubled over in pain, clutching my left side.

By 11:30, my entire chest felt tight and I was gasping to breath. Fearing the worst, I called for help.

I spent the rest of the day in the emergency room, doctors running tests. Fortunately, they determined it was not a heart issue. But it was clear my lifestyle had created the conditions for this scare.

Not even 30 years of age, my extremist workaholic lifestyle finally reared it’s ugly head…

When a doctor warns you that your work lifestyle is putting your life at risk, it’s sort of a wake up call that’s hard to ignore.

I felt the only real choice I had was to reevaluate everything.

Starting with my diet, exercise, and sleep routines – like cutting back from 12+ cups of coffee per day to 1–2 max, and prioritizing healthy eating. Then prioritizing regular exercise and 8 hours of sleep. These all made big impacts quick.

But they weren’t sustainable alone. I had to set boundaries and get mentally fit, too.

It was not easy.

I began weekly counseling and engaged with my boss. This was no way to live. I needed help and accountability.

Over the subsequent year, I experimented. I tried a number of different schedules and routines. I iterated often.

I fought a guilt trap – where working less made me feel paranoid, or like I was underperforming. It took consciously combatting this to overcome it.

The withdrawal from working aggressive hours also sent me into a minor state of depression. Because I had centered my life around my work, it was extremely difficult to begin finding meaning in other areas of my life again. But I made myself explore things outside of work. Eventually, this worked, too.

The countless experiments ultimately resulted in my removing a bunch of bad habits and replacing them with intentional decisions.

In time, I discovered how much power I had in deliberately designing my life – where I could find fulfillment in and out of work and everything else.

I don’t regret a single hour I put into the work I did – that ultimately pushed me to burnout. I truly loved my work. Instead, I just wish I’d have realized how important it is to have more than just work going.

The surest way to burnout is by not allowing room for any other meaningful activities in your life.

It happened to me. May you be wiser.

__

*This post was originally published on Quora in response to the question What are some tips for avoiding burnout in a highly stressful career?

The lights were off. It’s how I liked to work.

A faint glow from two 27” monitors and a MacBook Pro reflected off my glasses. Beneath my hoodie, the steady mind-numbing pulse of screamo bass outpaced the tap-tap-tapping from my keyboard.

I forgot how long I’d been there. I’d woken up around 4:30 am and I’d be there well until the evening hours.

Half a dozen years into my career, this was a typical day.

At least, until the day I had my first major health scare…

I stacked 80–100 hour work weeks regularly. No one made me. There was no formal “work hours” policy. Success was about results. But in the breakneck pace of a hyper growth company, there is never a shortage of problems or projects to get lost in.

That kind of environment is addicting, dangerous even. There’s an almost pornographic appeal to putting in long hours. Even when you tell yourself you’re having fun – which I was – eventually your faculties erode. The warning voice of conscience “you’re overdoing it” fades the longer you allow workaholism to prevail.

It doesn’t have to be this way. And probably it shouldn’t be. But it’s a picture of what life had become for me.

I ate like sh*t. Burgers. Pizza. Tacos. Fast food.

I rarely exercised anymore. Unless switching from standing to sitting or pacing on calls counts.

Not to mention the excessive intake – coffee to kickstart the day and alcohol to shut the mind off most nights.

Health took a back seat to work – both mental and physical health.

Then one day it went too far.

Not unlike any day, I rose early and slammed several coffees before anyone else made it to the office. But I remember it was a particularly stressful day.

That’s what set it into motion, I told myself: the stress.

It started as a small ache in my side. It slowly intensified through the morning. By 11 am, I was doubled over in pin, clutching my left side.

By 11:30, my entire chest felt tight and I was gasping to breath. Fearing the worst, I called for help.

I spent the rest of the day in the emergency room, doctors running tests. Fortunately, they determined it was not a heart issue. But it was clear my lifestyle had created the conditions for this scare.

Not even 30 years of age, my extremist workaholic lifestyle finally reared it’s ugly head…

When a doctor warns you that your work lifestyle is putting your life at risk, it’s sort of a wake up call that’s hard to ignore.

I felt the only real choice I had was to reevaluate everything.

Starting with my diet, exercise, and sleep routines – like cutting back from 12+ cups of coffee per day to 1–2 max, and prioritizing healthy eating. Then prioritizing regular exercise and 8 hours of sleep. These all made big impacts quick.

But they weren’t sustainable alone. I had to set boundaries and get mentally fit, too.

It was not easy.

I began weekly counseling and engaged with my boss. This was no way to live. I needed help and accountability.

Over the subsequent year, I experimented. I tried a number of different schedules and routines. I iterated often.

I fought a guilt trap – where working less made me feel paranoid, or like I was underperforming. It took consciously combatting this to overcome it.

The withdrawal from working aggressive hours also sent me into a minor state of depression. Because I had centered my life around my work, it was extremely difficult to begin finding meaning in other areas of my life again. But I made myself explore things outside of work. Eventually, this worked, too.

The countless experiments ultimately resulted in my removing a bunch of bad habits and replacing them with intentional decisions.

In time, I discovered how much power I had in deliberately designing my life – where I could find fulfillment in and out of work and everything else.

I don’t regret a single hour I put into the work I did – that ultimately pushed me to burnout. I truly loved my work. Instead, I just wish I’d have realized how important it is to have more than just work going.

The surest way to burnout is by not allowing room for any other meaningful activities in your life.

It happened to me. May you be wiser.

*This was originally published on Quora in response to the question What is your advice for avoiding burnout in a high stress career?

 

Bob is excited.

He hasn’t been on a date in a while and Alice was pretty enough he told himself.

Bob’s mom had told him to just keep being himself and eventually the perfect “one” would come along. Is this the night she’s right?

No. Bob’s mom is wrong again.

Alice is nervous.

Alice gave Bob her number after meeting him at a bar last week. He seemed nice enough – and nothing looked too creepy on his instagram.

Alice has been on so many bad dates she stopped getting her hopes up.

In other words, the bar for a good date in Alice’s book is REALLY low.

But Alice is about to be disappointed again.

---

RED FLAG NUMBER 1*

When Bob first saw Alice, he was half-buzzed at the local sports bar. He elbowed his buddy Jim, “Hey, Jimbo, smoke show at 5 o’clock, checker out!” Before Jim could stop him, Bob made a beeline for Alice.

Only God and Alice know what he said, but to Jim’s surprise, Bob came back with her number.

A few days later, Bob told Jim he and Alice were going to dinner.*

---

RED FLAG NUMBER 2**

Instead of offering to pick Alice up, Bob tells her to meet him at the restaurant. Bob chose a local dive bar that has great burgers. Alice has never been, but decides maybe it could be fun.

Bob has already been there for a couple hours. He’s sitting at a table with several other guys. Alice walks in and Bob does one of those awkward hand gestures in the air to motion her over. When Alice walks up, Bob tells his friends, “This is the girl I was telling you about.” When Alice walks up, Bob high fives her.

Alice, polite, plays along.

---

RED FLAG NUMBER 3***

Alice tries to make polite conversation with Bob. She figures she’ll give it a chance. But Bob doesn’t get it. Instead of reciprocating questions, Bob talks. And talks. And talks.

Bob drones on about everything from his ex girlfriend and his fantasy football roster to how much money he makes and how cool his friends think he is.

Bob doesn’t ask Alice any questions. Instead, he tries to impress her by talking the entire time.

---

RED FLAG NUMBER 4****

After an hour and a half nonstop soliloquy, Alice interrupts Bob to attempt an exit. Bob hardly takes notice at first and keeps talking. Alice has to stand up from the table for Bob to break his stream of consciousness.

Bob – thinking the date went great – invites Alice over for a night cap. She politely declines.

Bob: “We should do this again sometime.”

Alice: “I don’t know if that’s such a good idea.”

Bob: “Really? I thought we had a great time.”

Alice: “Thanks for dinner, Bob. I really better be going.”

---

Assuming the candidate isn’t an axe murderer and brings it up in the interview – the above scenarios cover a number of the most common red flags to run away from. If you’re a hiring manager and have ever felt like Alice, God bless you.

*RED FLAG NUMBER 1:

Let’s pretend Bob is the candidate. He doesn’t know anything about the company – but he heard it sounded cool. He does no research before showing up. He took no notes on his initial phone screen call. Bob treats this role and company as if it’s no different than any other company.

Bob’s approach to the job hunt is like a drunk guy on a bar hitting on girls – with a quantity over quality approach. If Bob just hits on enough girls, surely one will talk to him.

This often comes out in the interview quickly. Look for key phrases from the candidate like, “What do you all do here?” or “I just thought the company sounded cool.”

**RED FLAG NUMBER 2:

Bob shows up to the interview unprepared. It looks like he rolled out of bed and made no effort to present himself. Plus, he’s behaving way too informally – acting chummy like everyone is an old college buddy.

He talks about the position as if it’s already a foregone conclusion. He’s not making any extra effort to stand out.

***RED FLAG NUMBER 3:

During the interview, Bob drones on and on. He takes 5 minutes or more to answer every question. He talks only about himself. He overshares information. He talks poorly about former employers and co-workers. He blames other people for mistakes. His best examples of experience are things that don’t indicate he has a depth of knowledge or expertise in.

Bob also asks no relevant questions himself. Bob takes no interest in the interviewer, the company’s mission, or the results that drive the role he’s applying for.

Bob does not reference how he can create value for the company – and seems entirely unconcerned with value creation. Instead, Bob focuses solely on himself.

***RED FLAG NUMBER 4:

Bob demonstrates he is socially unaware. Both from his interactions with the people he’s encountered while on site and the way he phrases some questions.

Bob borders on inappropriate with some comments. Something strange about Bob just gives you a creepy feeling, too. Bob tries to extend the conversation beyond the point it has clearly ended – suggesting he’s not aware nor respectful of others’ time.

Bob is also over-assuming. He behaves as if the interview is nothing more than a formality to get the job.

Don’t be like Bob.

*This post was originally published on Quora in response to the question What is the biggest red flag to hear when being interviewed?

This is a story about Jack.

Jack wants a job. Any job. He needs money because allowance from his parents isn’t paying the bills anymore.

But Jack has never had to apply for a job before. So he did what most people do. Jack Googled “How do I get a job?”

After getting lost reading several dozen how-tos and subreddits Jack got worried. None of the advice told him what he could do today.

Jack was sad, confused, and still broke.

Jack doesn’t have any experience. He doesn’t have a resume – let alone a “good” resume. He still needs a job and his online reading made him feel like an unqualified loser.

But Jack wasn’t going to give up that easy. He decided he’d go visit some local businesses in-person to see what he could do.

The first place he visits is the grocery store, where he’s greeted by a manager. Jack asks him about the now hiring sign he saw outside – “How could I work for you?”

The manager tells him that he’s looking for people who will work hard and show up on time. He asks Jack if he can do that.

Jack tells him he’s never had a job before. “I’m willing to give it my best try.”

The manager tells him he’s leery of anyone who has never worked before. “I’ve had a lot of people applying for this job, son,” he tells Jack, “Why should I hire you?”

Jack doesn’t know, so he tells the manager the only answer he can think of – the truth.

“Honestly, sir, I don’t know why you should pick me over anyone else, but I’m willing to do whatever it takes to learn.”

The manager tells Jack to come back Saturday for a test run. “You get one shot to prove yourself, don’t be late.”

On Saturday, Jack showed up early.

He got a new haircut the night before, and picked out clean clothes. His shirt is tucked in and he’s wearing a belt.

The manager greets him again. He tells him he’d like Jack to sweep the floor to start and points him to the back room where the brooms are kept.

Jack doesn’t wait for instructions. Jack races to the back room. He grabs the dust mop and he sets off around the store.

When he encounters guests, Jack politely waits for them to move.

One guest stopped Jack. “Sir, do you know which aisle I can find the grape jelly?”

Jack doesn’t know, so he tells her the only answer he can think of – the truth. “No, ma’am, I do not. But give me one second to find out and I’ll be right back.”

Jack races to the front of the store, reading the signs as he moves. There, on aisle two, he spots it: “Condiments.” And he tears down the aisle, grabs a jar of Smucker’s Grape, and hurries back to the customer.

“Ma’am, I went ahead and grabbed you a jar, but the grape jelly is on aisle two, so you know next time.”

The customer smiles and accepts the jelly. She tells Jack how nice it is to meet such a polite young lad, and that she’d have to put in a nice word with his boss.

When the manager heard the customer’s story, he found Jack and told him he’d like to give him a shot.

Jack’s heart did cartwheels. He found a job! But he wanted to be sure why. So he asked.

“Sir, if you don’t mind me asking, what made you decide to take a chance on me? After all, I don’t have any skills.”

The manager told Jack he passed the test with flying colors.

“You told me the truth. You showed up on time. You jumped to get to work when you first got here. You wore a smile. You put the customer’s needs over your task at hand. You’re just the kind of person we want to teach.”

Jack beamed all the way home that day. He knew he had learned a valuable lesson.

Getting a job wasn’t as difficult as he first feared.

It was okay he didn’t know how to get a job – because he was willing to ask what it took, and go out of his way to prove he could do it.

It was okay that he didn’t have skills – because he was honest about it.

It was okay that he didn’t have experience – because he was willing to prove he’d work hard to learn.

…

Jack’s story can teach us all a lot. Regardless of what job we’re trying to land.

Jack’s whatever-it-takes attitude, paired with his commitment to proving it paid off for him.

And next time you’re looking for a job, it could pay off for you, too.

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*I originally published this post on Quora in response to the question What is the best way to get a job easily?