The 7 Biggest Career Mistakes

I love talking to people who are 20–30 years older than I am.

Most of us end up going down similar life paths. We end up having similar goals, similar fears, similar regrets, similar anxieties, and similar “lessons learned.”

We all like to think we’re different, but we’re actually not.

So if you talk to people who are a few decades ahead of you, you can get a pretty good sense of where you’ll be when you hit their age if you keep going down the path you’re on right now.

That’s what I like to do — so at least I know what to expect.

A lot of us have similar things that hold us back from building careers we love. We say things like:

  • “I should just be happy with what I have.” (rationalizing why we’re not living up to our full potential)

But the select few who are at the top of their field manage to break past these mental barriers, while so many others remain stuck trying to “get their ducks in a row” for years on end.

Here are the mistakes most people make, that people at the top manage to avoid:

Mistake #1: Thinking your career should be linear

When you look at the career paths of successful people — people who worked alongside the world’s best entrepreneurs, VPs of Fortune 500 companies, etc — you’ll notice a common pattern.

Almost none of them “moved up the ladder” in a linear fashion. In fact, 99% of top performers have made at least one discontinuous “jump” in their career.

They might have gotten a normal analyst-level job right out of school, have normal responsibilities for a few years and then … BAM! They get a director-level role when they’re 26.

Or they land an insane promotion before they’re “supposed” to, while everybody else is sitting around waiting for their boss to notice them and their hard work.

For example, Ryan Holiday started out as a book researcher for Robert Greene. By 22, he was the Director of Marketing at American Apparel.

Cory Ames got a job at Firegang Marketing as an entry-level apprentice making minimum wage. Within a few years, he moved on to running their entire operations and eventually became CEO.

Extraordinary people don’t wait until they have the right “experience” or qualifications to make the leap — they just wait until they have the right skills.

There’s a big difference between skills and experience.

A 25 year old who has been reading, learning, and implementing new information for five years will have more skills than an “experienced” 35 year old who spent ten years coasting.

The more you focus on learning, the more exponential growth you’ll have. That’s how you “skip the line” in front of everybody else.

Mistake #2: Assuming that what got you to level 1 will get you to level 2

In the beginning of your career, your technical skills usually matter the most. For junior-level positions, you usually need to know how to design products well, write code, etc.

But as time goes on, those technical skills start to matter less. How you interact with people starts to matter a lot more.

To get from level zero to level one, you have to focus on your IQ. To get from level one to level two, you have to focus on your EQ — your emotional intelligence.

Most people think that if they just get good enough at their craft, then everything will be fine. They think that if they just get good enough, someone will “notice” them — and then everything will be fine.

And it’s true, being good at what you do does matter.

But you need much more than that. You need to know how to navigate the world of office politics. You need to figure out how to add value outside of your role.

You need to figure out what your company needs, and give it to them — even if they don’t tell you what it is.

Mistake #3: Getting distracted by “shiny object” syndrome

Once you reach a certain level, success isn’t about getting new opportunities. It’s about getting the right opportunities.

But it’s still really hard to detach yourself from “shiny object” syndrome.

Early on in college, I had quite a few jobs that I said “yes” to because they sounded pretty cool on the surface. The job description sounded fun. I thought I’d like it.

But it turned out to be soul crushing. One time when I was on a lunch break, I was chewing my food much slower than usual because I really didn’t want to go back.

The more time you spend looking for the next new opportunity, the more time you could’ve spent becoming the best what you’ve already got.

Mistake #4: Chasing after status

Average people chase after titles more than results.

They care more about looking high-status than actually being high status. They want to show up at their class reunion and be the most successful person there.

The truth is, there’s nothing wrong with this.

But counterintuitively, some of the best career opportunities you could get are actually not high status ones.

Gary Vaynerchuk’s old personal trainer followed him around all day, filling up his water jug and delivering meals to him. But he was able to skyrocket his online business because of how much he learned watching Gary do business.

George Millo dropped out of school, booked a one way flight to Vietnam, and worked for a location independent business as a computer programmer. The pay was terrible, and everybody probably thought he was crazy. But he learned more in that job than in college. He’s now a very well paid freelancer and while being booked months in advance.

Most people are so status driven that they will pass up the chance to take one step back today to take two steps forward tomorrow.

But people who chase results over status are the ones who eventually become high status.

Mistake #5: Not making “mini-failures”

Most people are held back by assumptions they’ve made that aren’t even true.

Their inner voice in their head magnifies the dangers of failing with every seemingly “risky” move they make. So they stay stuck in their comfort zone for years on end.

I get it.

When it comes to your career, failing can have some pretty severe consequences. What if you make the “leap” to something you really love doing, but lose the roof over your head? What if you put a lot of effort into another application, only to never hear back?

There’s this myth that successful people take big risks. But the truth is actually the opposite.

The most successful people I know are actually the most risk averse people I know.

Tim Ferriss once said that to the outside world, it seems like he takes massive bets and makes risky “leaps.” But behind-the-scenes, he does thousands of little “tests” to virtually guarantee that the big leaps will work out when he decides to make them.

When venture capitalists learn about a new industry, they don’t start out by making massive investments. They make tons of tiny bets, and once they get a feel for the market, they start making bigger ones.

Make lots of tiny low risk failures leading up to your big leap. That way, you can do it with confidence without feeling anxious.

Mistake #6: Not asking other people for help

One of the biggest misconceptions that people have when it comes to their careers is that strangers won’t care enough to help them.

In fact, the quickest way to avoid mistakes that could cost you months of wasted time and effort is by reaching out to someone in your field who’s a few years ahead of you, and asking them questions.

But many of us are afraid of looking desperate or sleazy. Or we think “why would they ever want to talk to me?”

In reality, people love to help. You just have to reach out in the right way.

Mistake #7: Trying to “figure things out” on your own

“A mind troubled by doubt cannot focus on the course to victory.” — Arthur Golden

One of the biggest differences between top performers and everybody else is that top performers test their assumptions, while most people try to figure it out in their own heads.

The more you try to create the perfect plan, the more you’ll think yourself in circles until your brain feels too cluttered to function.

Successful people look outward for answers while most people look inward.

That’s how they beat everyone else.

Call to Action

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Strategist for @GaryVee on @TeamGaryVee. Insatiably curious.

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