10 Career Mistakes I Wish I Had Never Made

“It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes.” — Warren Buffet

In the last decade, I went from student to entrepreneur to freelancer to climbing the corporate ladder to blogger to teacher.

Yes, that’s not a normal career path, and it’s also not what I ever expected. But life hardly turns out the way you expect.

That’s because we’re only human. And humans make mistakes.

Recently I received an email from a reader. He asked about my biggest career mistake.

That got me thinking. And writing. A lot. 

And after writing more than 2000 words about my career mistakes, I thought: “Wow dude, you’ve made every single mistake you possibly could.”

Anyway, I’ve cut out the obvious stuff and I made a list of my top 10 mistakes. I hope that one of the points is useful to you.

1. Assuming That Your Career Is Linear

That is, by far, the most important lesson I’ve learned. Firstly, I’ve learned that assumptions are always bad. We collectively assume a lot of things without ever asking or researching.

One of those assumptions is that careers progress linearly. Who ever said that? When I think about it, I have no idea why I believed that in the first place.

It goes like this:

  • You get an education.
  • Get an internship.
  • Stay put for three years.
  • Then try to become a low-level manager
  • After a few years you move up.
  • And if you stall, you move to another company for a better paying position.


  • You’re a freelancer.
  • You start doing work for free.
  • You keep doing that for years.
  • You can’t make ends meet.
  • You get a job.
  • You quit your job because you hate it.
  • You start charging for your work.
  • And you increase your rate a little bit every year.

Last one: you’re an entrepreneur, you start a business, you grow, you think you’re awesome, you spend more than you make, you try to get investors, they own you, and you fuck up.

Again: Why do we do that stuff? It’s so predictable. Life’s way too short for that boring stuff.

Accelerate your learning curve. Focus on value. Learn more, earn more. Make leaps. And sometimes when you learn, you take a step back. But that’s fine because you will earn more in the future.

In today’s economy, it’s more about what you have to offer. For the first time in history, a lot of companies (not all) don’t look at age, gender, race, degrees — they care about what you have to offer.

So offer some great work. How? Learn faster. Access to information has never been this easy. Use it.

2.Prioritizing Money

I’ve done this. And if you do that, there are three things that can happen:

  1. You end up in a sales job you hate.
  2. You become an aggressive sales oriented business or freelancer.
  3. You say yes to work that crushes your soul.

There’s nothing wrong with those things, but they are not sustainable. I’m not trying to stop you from earning some cash money.

But instead of focusing on money; why not focus on other things that are more fulfilling? Things like learning, experience, doing work that you are interested in, adding value to other people’s lives.

Will most people follow this advice? Probably not because they can’t say no to money. There’s only one simple rule to money and freedom: Live beneath your means. And yes, that’s hard.

If you want to know more about how you can train yourself not to depend on money, please read Seneca — Letters From A Stoic. He writes about it a lot.

3.Wasting Time

You won’t believe how many evenings and weekends I’ve lost by watching tv, going out, pointless shopping, or whatever leisure activity.

Sure, entertainment is good, but you don’t have to relax every SINGLE free minute you have.

Look, this is your life, and this is your career. Take it seriously.

Can I ask you something? What’s your skill? What are you exceptional at?

If you don’t know the answer, it’s time to get down to it. Start learning, practicing, doing, whatever. Do something that turns you into an expert at something.

4.Choosing A Job Over An Industry

In the last decade, I’ve tried my luck in several industries, including hospitality, fashion, IT, and banking. But in recent years, I’ve only committed to consulting and education.

I wish I did that earlier. Hopping from industry to industry has huge costs. You have to learn the industry, market, people, unwritten rules, you name it.

Most people decide what they want to be (or they just roll into a profession). And then they try to find a job—they don’t care about the industry as long as it pays. Or, they want to be an entrepreneur or freelancer and they follow the money.

But that’s not an effective strategy on the long-term because you will never become an expert at something. Instead, pick one or two industries that you love, and commit to finding an opportunity there.

5. Getting Comfortable

“Ah, I’ve worked hard and now I’m good.” Think again. You’re never safe.

Life is competition. The next person is waiting patiently until you mess up, and then they will swoop in and take your position.

Is that really true? Well, to be honest, I don’t know. But I sure like to think that’s the case.

Why? Because that keeps me on my toes. The last thing you want is to become comfortable.

6. Not Asking For Things

Yes, you’re a nice person. We get it. But don’t be too nice.

Other people will take your spot, push you over, and you will end up with nothing. You don’t have to be a dick. Just know that when you’re in business, it’s business.

And everything is business: Art, sports, media, work-relationships, colleagues, you name it.

If you want to get something, you have to ask for it. Want a raise? Ask. No one will give it to you. What did you expect?

“Oh hey, you’re such an awesome person. Here’s a free bag of money.” Never going to happen.

7. Not Following Your Interests

There are two camps on this topic. People who say you should follow your passion, and people who say you shouldn’t.

The funny thing is, the people who say that you shouldn’t follow your passion, didn’t follow their passion. Get it? Why on earth would they encourage others to follow their passion? And vice versa.

Now, I don’t really like the word passion—and I don’t like the whole discussion. But all I can say is this:

Life is not infinite. Do you really want to spend your time doing shit you hate?

8. Not Listening To People

When I got my Master’s degree in Business Administration years ago, I thought I was the man. I didn’t listen to people who were more experienced than me. Big mistake.

Practice is different from books. I didn’t realize that.

Now I prefer to be humble and listen to everyone. Also, that means listening to less experienced people. They often have the best ideas.

9.Wanting Too Much, Too Quickly

Even though your career doesn’t have to progress in a linear fashion, you can’t make giant leaps every single day. And in the beginning, I especially tried to move too fast.

But now I’m more patient. Before I started blogging, I’d written hundreds of essays when I was getting my degrees, and not to forget two big ass theses.

And I’ve worked in the trenches of business and marketing for years before I started coaching/consulting. No one ever saw that. And that’s fine because that’s how you learn.

10. Not Asking For Help

Maybe you’re too proud. Maybe you think people will believe that you’re stupid. Maybe you’re not raised that way.

But if you don’t ask for help, one thing is sure: You will never get it.

Almost everything in life is a team effort. Even if you work entirely for yourself, you still need people. And they need you.

The “Self-made” success stories are all fake.

Whenever you’re spreading too thin, reach out to others. Reach out to colleagues, partners, friends, family. They will help you, and if they don’t, they’re not your friends.

Finally: This Is Your Career.

Why NOT take it seriously? That’s one thing I didn’t do enough until a few years ago. I was too passive.

If you find yourself unhappy with your career, or how it’s progressing: Change. That’s the only universal advice there is.

And do it today. You know why? If you don’t do it today, when will you?

You and I both know the answer to that.



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  1. Your article hit home – well said. It made me think about my 30+ year career all for the same corporation.

    I had the opportunity to get an MBA paid by the company. They (school) stressed having a broad background so I followed their advice and hopped around as I slowly climbed the ladder. I felt I built a keener insight into how to make them a better company and me a better resource to them – unfortunately I lost my sponsors along the way. These were the people that were helping me but I kept leaving them. I also started to wander into fields I was not as good at so my performance suffered making my journey back to my strengths (sales & marketing – not finance) much harder to make.

    Point 6 – this has always annoyed me. As a manager, having an employee ask me for a raise or promotion generally came at the wrong times or in the wrong ways. Let me explain. As a manager I held a performance review each year with those on my team. I had lesser discussions during the year but I know many managers do not like to do this or don’t do it at all. I found that we ‘managers’ discussed raises and promotions well before the performance review. Ask how you can improve your performance or explain to your manager that you want to be considered for another position at some point. This allowed me to help work that person into that position without the confrontational approach. I also know that some managers held onto talent and did not let go of them or want to support talent moving on. Unfortunately to get good talent requires being able to let good talent go – good talent knows a dead end job usually. I’ve also seen people fight a position or job suggested to them. It might come as a surprise but as an employee – managers develop ‘opinions’ about you and see a good fit that you might not see. I’ve found that electing to go and try it might be much better than you thought. So go where you are wanted. Fighting for that one special dream job usually disappointed me once I got it.

    Look forward to your next article.

    1. Thanks for sharing your thoughts, Scott! I think a lot of people can relate, and can learn from what you just shared. Also, spot on about the dream job. I can relate. Thanks for the contribution!

  2. Love this! Looking forward to reading more of your writing! I have to go back to work tomorrow after 4 weeks off from FMLA leave, and I really just want to tell them to shove the job up their ass! I have worked for the same company for 17 years, first job I ever had, and I am over it. Over the last couple weeks I have turned in numerous applications to jobs and filled out a resume, in which was very short with only having one job listed as Work History. I have not had any luck with call backs, but am anxious to hear anything! “Life is not infinite. Do you really want to spend your time doing shit you hate?” Fuck NO! Think I might just quit tomorrow anyway!

    Thanks for the Great Read!


    1. Hey Carl! Good to hear that you’re motivated. One thing I always like to remind myself is: Stay practical. Sometimes it’s practical to keep a job while we’re working on a business, or while we’re searching for a new job. Let me know how it goes.

      1. True, Staying Practical is Key. I’m currently doing the same. Keeping my job and striving towards other things.

        Darius, what do you think about one person wanting to do or achieve many things? How does one pursue all their goals and dreams?

        1. I think that, realistically, you can’t achieve all your dreams. Life’s too short to do everything. Just pick a few things you’re extremely passionate and good at. That’s often the best recipe.

  3. Darius a very nice piece of insight into careers. I personally feel that having a mentor is one of the best hope for a brighter career, but it is very rare to find a right person who can guide you in your domain. Other option is to read a lot to get the right info and then make decisions.

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