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Every Successful Leader You Know Has Experienced (At Least) One of These Massive Setbacks

Successful Leaders

Photo by David Huck on Unsplash


On day one of a new job I feel like a fraud.

My smile is fake. My palms are sweaty. I run to the toilet a lot for fear poos.

Basically, I have no clue if I can do even 20% of what’s in the job description. I wing it. I tell the hiring manager what they want to hear so I can pay for my shelter. I return home each night to my bat cave, thinking “what the hell have I done?”

It lasts about three months. Then I’m sweet as.

In my last job people thought I was hitting home runs every day. They couldn’t lift the veil and see inside my head full of fear. None of us can. Leaders look like geniuses — until they tell you the truth about their careers.

Every successful leader you know has experienced (at least) one of these seven massive setbacks.

1. Taken a new role and felt like an imposter

Leaders take roles they’re not qualified for all the time.

My old boss used to say, “every leader is trying sh*t on to see what sticks. If they get away with it, then great. If not, they’ve lost nothing.”

The challenge is you can fake your way into a new role. You think you’ll learn as you go, but not always. Sometimes the leaders at your new gig need results straight away. They don’t have time for you to learn.

When they realize they’ve been oversold they put you under enormous pressure to get to the truth. Your career can fracture into a million pieces from all the pressure. They’ll either get rid of you, or force you to step down or cop a demotion.

It’s better to oversell and fail than undersell yourself and go nowhere.

2. Been betrayed by another leader

Workplaces are a game of thrones battle.

When you’re a leader you’ve got supporters and haters. There is always politics to navigate. Everybody has their own agenda. Whichever leaders get their agenda done, wins the prize: a fat cat bonus.

Through the process there’s always one sly bastard that betrays you. You think they’re on your side. Secretly they’re talking smack about you to the big bosses to get you in trouble — normally, so they can march in and take your leadership gig right off your hands.

Leadership politics is a nightmare. It’s one reason I quit working a job forever.

It sucks to get betrayed, but humans let each other down. Expect it so you don’t get wrecked by it.

3. Worked an entry-level job

I started my career at 12-years-old working in the local pizza shop. I later got a promotion to work in a hotel. Scandalous couples would rock up to reception all through the night and try to look innocent.

They were there for a naughty time. I had to keep a straight face and pretend I had no idea why they wanted a room at 1 AM.

We all start in humble beginnings.

Every big shot leader you know worked their fair share of entry-level jobs too. It can feel like a setback when you work one. You can feel like you’ll never get anywhere. Even worse, if your career explodes (like mine did) you can find yourself back in an entry-level job.

There’s a huge advantage: when you’ve worked entry-level jobs, it helps bond you better to frontline workers that do the majority of the heavy lifting.

4. Battled mental health issues

Take one look at LinkedIn. It’s clear since March 2020 that mental health issues are common amongst leaders. Unfortunately, mental health is still seen as a career weakness. I’ve been told to shut up about it plenty of times.

Make no mistake. Anxiety or depression has affected ever flawesome leader. They just don’t talk about it. I wish more would.

Talking leads to healing.

5. Felt like giving up

As the leader there’s nowhere to hide. You’re accountable for the results.

Sometimes the goals you’re set are nothing more than wishful thinking. A group of strange folks in pinstripe suits make random decisions about an idealistic revenue number or target.

This happened in 2020. My boss told us that we had to exceed targets. We explained that coroni-macaroni might make that hard. We got ignored. We had to tell leaders stupid stories about revenue that would never happen.

Meanwhile our competitors lowered their targets and focused on building goodwill with customers through honesty. They later thrived. We got hit by a leadership freight train. Leaders’ heads rolled.

It’s normal to feel like giving up at some point. The key is to persist. The truth eventually surfaces. Mother Nature takes out the trash.

6. Been rejected for multiple leadership roles

I’ve known many successful leaders that took a redundancy. I thought they would get a new job fast.

Only once you have behind the scenes conversations, is the truth revealed. Leadership roles are hard to get. Many people want them.

The best leaders only get hired because they can pass the minimum threshold of rejections needed to succeed.

7. Experienced personal tragedy and not wanted to go to work

I went to work many times right after I said goodbye to dead people. You’d never know it. I could act my way through it (mental illness teaches you).

The most successful leaders are where they are because of the tragedies that shaped them. Tragedies are inspiration that leads to an unusual form of motivation for a team. Tragedy extracts all the normalcy from your brain and spits it into the gutter.

Never forget …

  • Leaders get cancer
  • Leaders go bankrupt
  • Leaders lose loved ones in tragedies
  • Leaders give birth to stillborn babies
  • Leaders get addicted to illegal drugs
  • Leaders gamble away their life savings

Leaders aren’t special, they just look like they are. They’re like you and me.

It all boils down to this

People at work look like they’re winning

It’s all an act.

We’re all trying to make it through the day. We’re all uncertain about the future. We’re all scared out of our minds.

Don’t let corporate marketing or LinkedIn make you think any leader is winning every day.

We’re all just figuring stuff out as we go.

Career fear is normal.


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Tim Denning
I am an Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship. You may have seen my work on Medium, LinkedIn, Bitclout, or Twitter.

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