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