093: Stop Chasing Your Dream (the Wrong Way) [Podcast]

Everybody who leaves a day job to pursue their craft is blindsided by an abundance of something they never anticipated: time. No one sees it coming and no one ever warns you about it.

Stop Chasing Your Dream the Wrong Way

The same thing happens to high school graduates who go onto college. One day their lives are regimented from dawn to dusk with school, sports, homework, and chores. The next day they have a few classes and untold hours of free time that no one taught them how to manage.

When you’re pining for the day you’ll walk out the office door and go pro, you don’t think about how to use all the free time you used to spend working at your desk. “Work” takes on a new definition and the sudden volume of time available overwhelms many.

This week on The Portfolio Life, Andy and I talk about what I did wrong when starting a full-time writing career, and what you should do instead.

Listen in as we discuss the wrong way to build a blog, establish a platform, and refine your voice.

Listen to the podcast

To listen to the show, click the player below (If you are reading this via email or RSS, please click here).

No more Mr. Nice Guy

I know this guy who always went after the wrong girl. He was a nice guy, a sappy romantic really, and he’d fall head over heals for these girls who just weren’t that interested in him. No matter how many times he held the door open, or bought them flowers, he couldn’t win their hearts.

He tried too hard to tell a girl what he thought she wanted to hear, and live up to this stereotypical persona of the perfect guy portrayed in romantic comedies. It never worked.

One day, in a fit desperation, he gave up trying to play the “game”. He was still a good guy, but he stopped trying to fake it, and instead held a healthy confidence in who he was and what he had to offer. Two weeks later, he met his future wife and they celebrate their 10th wedding anniversary this year.

I’m not saying you’ll magically bump into your soulmate or get a book contract dropped on your doorstep, but when you stop trying to succeed at the wrong thing, or even the right thing in the wrong way, you can’t imagine what the future holds.

Show highlights

In this episode, we discuss:

  • What not to pursue on your journey to writing full-time
  • The eight times I tried blogging before getting it right
  • Why chasing what you think people want to hear leads to failure
  • Resisting the temptation to chase a quick buck
  • Connecting your skills and passion with what your tribe needs
  • Avoiding extremes when it comes to building a business
  • The fastest way to (almost) guarantee you succeed
  • Redefining what work looks like when you quit a day job
  • One thing most entrepreneurs are unprepared for


  • The worst kind of failure is succeeding at the wrong thing.
  • Fear obscures the bigger picture and distracts our focus from the goal.
  • Succeeding at something we don’t really want to do is a trap.
  • What makes an audience meaningful is they care about what you have to say.
  • Passion and money aren’t bad. They have to work together in order for you to feel good about the work you do.
  • It’s always easier to do the wrong thing than it is to do the right thing. Which is what makes the right thing so hard.


What are you doing to pursue your unique voice instead of trendy topics? What are you doing to avoid the traps I fell into when I started my writing career? Share in the comments

11 thoughts on “093: Stop Chasing Your Dream (the Wrong Way) [Podcast]

  1. Most of the audience running after trendy topics but we can divert them to our way by changing style of presentation of a unique topic. Its not an easy task to grab the audience for something different and unique, but once it has been done, then it will be forever.

  2. I have been using my free time to work on my development as person. I realized that trying to give other people a good impression of yourself do not mater, after all, you are the only that knows the abilities you have and how this make you complete all your goals. Also that certainly you don´t need to give up at any moment, but you must be careful at analyzing your goals, maybe they aren´t your best option and you will not be able to take advantage of them when you achieve them.

  3. I read this article because the title cought my attention, but i really think i made the right choice, this article rimind me what i was doing wrong all my life,but speccially i think it will help me a lot to be the person i want, i have to change my personality, i have to be the person i want to be and not to let me guide by other persons because to reach the hapinnes you have to be yourself.

  4. A great article, mainly because it tells the truth about almost every teen in the world, even I was doing this in my junior high school, where all my classmates talked with bad words and acted like if they were the bad boy of the group, they also used to show of the parties they went every weekend, so I started talking with bad words and acting in bad ways such as not doing homework or even to answer in a bad way to a teacher, now that I´m in high school I realized that this happened because my friends weren´t the right ones, in this month’s I´ve met amazing people that I know I don´t have to be someone that I really haven´t been, they accept me day I am and don´t have to change anything to have their friendship.
    My teacher recommended me this blog, and it´s amazing! I plan to be reading it more frequently to find more interesting articles like this, it´s very useful to know other people thoughts about different themes of life and you can learn new things about every topic you want so I consider this is a great tool for us to acquire knowledge :).

  5. Well hi; I’m a new reader of your blog. My teacher recommended it to me, and I need to admit it is amazing! I wanted to comment specially about this entry of your blog. I consider it very useful in all ambits of our life. Sometimes you are to focus on accomplishing one thing that you totally forget about what really maters. That kind of thing happens to me every time and it’s hard for me to notice what I am doing wrong. It really helped me to find a balance in my lifestyle. It also gave me hope to achieve my dreams and to never give up. Thank you!

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