9 successful people share the toughest lessons they learned at their first jobs

Alli Webb Mike LandauDrybarAlli Webb and Michael Landau, cofounders of Drybar.

The Success Series is a collection of the best career and life advice from some of our favourite writers, thinkers, and leaders.

For this instalment, we asked CEOs, authors, and entrepreneurs: What advice would you give to someone just starting their first real job?

Read all the articles from this and other installments of The Success Series here.

James Altucher: Don't dwell on failure and its supposed benefits -- there are none.

James Altucher is an investor, writer, entrepreneur, and the author of 'Choose Yourself.' Read more from Altucher at his blog, The Altucher Confidential.

I don't regret anything that has happened since. I've fallen many times. Sometimes I've gotten up, sometimes I've stayed down for quite a while. But no matter what, I'm glad I ended up right here.

That said, I'm not a big fan of failure. Everyone always says, 'You need to fail to learn.'

This is total BS. Failure is very painful and ugly and helps nobody. Often it's inevitable as we learn, but it's best to never fail so hard you are scared and anxious for life, family, love, career, whatever.

How can you avoid it? All of the advice is cliché, but I don't care. If I could advise someone who was in my exact position here is what I would say.

1. Make a list of five people you admire the most.

Read everything about them. Write down things you can do to be more like them.

Remember you are the average of the five people you surround yourself with. But don't forget they can be virtual mentors as well as real-life ones.

2. Write down ten ideas a day.

When I was at my lowest points, with no money in the bank and no prospects, I'd go out early, grab my coffee, read a book, and then write down 10 ideas every day.

Sometimes business ideas. Sometimes ideas for books I could write. Sometimes ideas for ways I thought other companies could be improved. And then I would send them those ideas.

Eventually, they responded. Eventually they paid me money. You can do this inside of a company as well.

Always remember: The key to wealth is to create wealth for others, whether you are an employee, an entrepreneur, or an entre-ployee.

Check out the rest of James Altucher's advice here.

Danny Rubin: Say 'yes' to the unfamiliar.

Danny Rubin is the creator and writer of News To Live By, a blog for Millennials that highlights career and leadership lessons hidden in the day's top stories.

It's December 2007. Fresh out of graduate school, I had a fancy master's degree in broadcast journalism from the University of Maryland-College Park -- and zero job prospects as a news reporter.

A week after graduation, I was thrilled to land an 'informational interview' at a TV news station in my hometown.

So there I was at 23 years old, nervous and clammy in a suit and tie and fully expecting a 10-minute 'nice to meet ya and off you go' conversation.

I sat down in front of Shane's desk. He had demo reels (work samples) from other hopeful reporters piled high on his desk. He looked over my own reel (stories I did in college) and told me the many ways I needed to improve.

I knew I was raw, but the criticism still hurt. I composed myself and told him, 'Great tips. I'll work on those things. Thanks.'

Just as I felt our chit chat had come to an end, Shane looked up at me, smiled wryly and said, 'Do you have ice in your veins?'

I took a gulp and felt a knot in my stomach at the same time. But without hesitation, I shot back, 'Yes, I do.'

'Good,' he said. 'One of my reporters is sick today, and we need to cover a submarine deployment at the naval base. Why don't you handle the story, and if I like your work we'll consider using it on the air tonight?'

My response on the outside: 'Sure. Thanks for the opportunity!'

My response on the inside: 'Holy #%@! Is this happening?!?!'

Check out more advice from Danny Rubin here.

Ryan Holiday: Find canvases for other people to paint on.

Ryan Holiday is the author of 'The Obstacle is the Way.' He is former director of marketing at American Apparel and dropped out of college at 19. He gives monthly book recommendations here.

When I first got a job as an assistant in Hollywood, someone told me that the best thing I could do as an assistant was to make other people look good.

It ended up being decent advice, but I've since come to understand that the wording wasn't right. It's not about just sitting there and working on the way people think about your boss or company.

The way I would explain it to a younger version of myself:

Find canvases for other people to paint on.

That is, completely ignore getting credit, getting ahead, even throw out what your job is supposed to be on paper. Instead, focus all your energy on finding, presenting, and facilitating opportunities that help other people inside the company succeed -- particularly the people you directly report to.

Check out the rest of Ryan Holiday's advice here.

Kara Goldin: Embrace being at the bottom of the totem pole.

Kara Goldin is the founder and CEO of Hint Water.

My years as an entrepreneur have provided me with so much insight and discovery -- I would be lying if I said I wouldn't have benefitted from having that understanding at the outset.

The truth is that many of the most important lessons come only through a process of trial and error, and I'll leave those for you to uncover in your own time. But the rest is yours for the taking, and I'm more than happy to share.

First and foremost, embrace the bottom of that totem pole. My first job was as an executive assistant at Time, Inc., a division of Time Warner. Many people there were just clock-punching, and I could have gone that route -- I was a mere assistant, after all.

Instead, I learned my boss's schedule and made sure my face was the first thing she saw in the morning and the last thing she saw on her way out. I gladly took any responsibility she threw my way, and even pitched new tasks for myself to take on.

Eventually, my role had outgrown my original job description, and I was a critical member of the team. You may think that an entry-level position is beneath you or a dead end, but it is what you make it. Dig your heels in, and make a name for yourself.

Check out more advice from Kara Goldin here.

Tim Ferriss: You are the average of the five people you associate with most.

Tim Ferriss has been listed as one of Fast Company's 'Most Innovative Business People,' Forbes Magazine's 'Names You Need to Know,' and is the seventh 'most powerful personality' on Newsweek's Digital 100 Power Index for 2012. He is an angel investor/advisor and author of 'The 4-Hour Workweek,' 'The 4-Hour Body,' and 'The 4-Hour Chef.'

Here's all of my career (and life) advice in one sentence:

You are the average of the five people you associate with most.

If I had more space, I'd add that studying accelerated learning is the Archimedes lever for everything else.

It's impossible to predict the future, but you can ensure maximum options by being adaptable, which you achieve through 'meta-learning' as a toolkit.

That was the goal of '
The 4-Hour Chef' -- to teach this toolkit using detailed examples from sports, investing, etc.

Think it takes a lifetime to learn a language? Not true -- you can become conversationally fluent in most languages in 8-12 weeks, including 'hard' languages like Japanese or Arabic.

Ditto with coding, graphic design, etc.

Job requirements will change, skill sets will evolve, tools (e.g. C++ versus the latest and greatest) will rapidly replace one another ... and it's not the strongest who survive. It's the most adaptable.

Nor do the big eat the small.

In a digital world, the fast eat the slow.

Alexa von Tobel: Get up, dress up, show up.

Alexa von Tobel, CFP®, is the founder and CEO of LearnVest, and the author of New York Times bestseller 'Financially Fearless.'

One of my favourite mottos is get up, dress up, show up -- wake up excited for what's coming, dress the part, and always show up ready to go.

As a new hire, you will likely find yourself in tons of new situations, and it's up to you to figure out how to navigate them.

Remember that your manager is strapped for time, so know when to ask questions. Are you unsure of the objectives for an assignment? Asking her to clarify is crucial, since it's pretty hard to make the mark if you don't know where it even lies.

On the flip side, avoid bombarding your manager with petty questions that could be answered by your peers or a quick Google search.

Read more advice from Alexa von Tobel here.

Cal Newport: 'Follow your passion' is bad advice.

Cal Newport is the author of 'So Good They Can't Ignore You,' which argues that 'follow your passion' is bad advice, and then explores what career strategies work better.

Toward the end of a high profile panel discussion on job creation, held during the 2012 Democratic National Convention, the conversation turned to a ubiquitous piece of career advice: follow your passion.

One panel member in particular disagreed with this suggestion: Steve Jobs biographer Walter Isaacson. It wasn't Isaacson's dissent that caught the audience's attention, however, but instead his revelation that the late Steve Jobs agreed with him.

'I remember talking exactly a year ago right now to Steve Jobs, who was very ill, and I asked him that question,' Isaacson said.

He then recalled Jobs's response:

'Yeah, we're always talking about following your passion, but we're all part of the flow of history … you've got to put something back into the flow of history that's going to help your community, help other people … so that 20, 30, 40 years from now … people will say, this person didn't just have a passion, he cared about making something that other people could benefit from.'

Isaacson's summary of this perspective was harsher:

'The important point is to not just follow your passion but something larger than yourself. It ain't just about you and your damn passion.'

This story came to mind as I was pondering what advice I would give to someone just starting out in the working world, as I think it presents a sustainable and effective path to meaning and satisfaction, especially as compared to simplistic slogans like 'follow your passion.'

Alli Webb and Michael Landau: It's much easier to teach skills than it is to teach attitude and passion.

Alli Webb and Michael Landau are the cofounders of Drybar.

For us, it all starts with finding people who share our passion and have an obsessive focus on the customer experience. We've learned (sometimes the hard way) that it's much easier to teach skills than it is to teach attitude and passion!

One good example was a girl who came to a stylist audition in the very early days. It was clear that she didn't have what it takes to be a Drybar stylist. However, she followed up with an emphatic desire to be a part of our company, and offered to be an assistant or 'do anything to work here.'

Well, she ended up being one of our best hires, working her way up through the ranks and eventually becoming one of our top regional managers.

Shane Parrish: Goal-oriented people often fail.

Shane Parrish is an entrepreneur and the founder and CEO of Farnam Street.

Looking back on my first years out of school and the countless mistakes I made, I can't help but feel that any success I've enjoyed is more through dumb luck than any particular brilliance on my part.

While unqualified, I'm often asked to give advice to young people who are just beginning their own journey of self-discovery. With that disclaimer, let me share a few things that help me navigate my own journey in the hopes that these landmarks help you navigate yours.


Just because we've lost our way doesn't mean that we are lost forever. In the end, it's not the failures that define us so much as how we respond. Learn to recognise mistakes and correct them. (see #2.)

Goal-orientated people mostly fail

Goal-oriented people mostly fail. What you really want is a system that increases your odds of success. Even if that system only improves the odds a little it adds up over a long life.


Friendship is more than just being there for your friends. Being a great friend means that you let your friends be there for you.

Next, check out the weird stuff successful people keep at their offices ...

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