5 Things Nobody Tells You About Chasing Your Dreams

As someone who sold cassette tapes in elementary school, I knew that one day I would be become an entrepreneur. In January 2014, at the age of 33 with a family and two young kids, I decided to chase my dream and go full-time in my app marketing business.
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As someone who sold cassette tapes in elementary school, I knew that one day I would be become an entrepreneur. In January 2014, at the age of 33 with a family and two young kids, I decided to chase my dream and go full-time in my app marketing business.

In this era of online businesses and shows like Shark Tank, I think that entrepreneurship is glamorized. Everyone wants freedom, but having freedom comes with thousands of tiny mental scars that people are too ashamed or embarrassed to talk about.

Three years into running my own business and making more money last year than I ever did in corporate life, I will share five brutally honest things that I went through that I wish others had told me about chasing your dream.

1. Relationship Scars

Going from making six figures to not exactly knowing how you are going to make money puts a huge strain on your relationship. While my wife is fully supportive of me chasing my dream, she also wants to ensure that we are planning for our kids’ futures.

My wife and I argued many times, often bringing up divorce. It wasn’t that we were in any financial trouble, but the lack of stability added a strain in our relationship.

My lack of confidence in my business and, frankly, myself made her feel more unstable. While we are still happily married, there are scars that she and I may never get over.

2. Self-Doubt

Three months into chasing my dream, I felt like I was living my dream. I was an entrepreneur making good money and having the freedom to work whenever I wanted.

Then, out of nowhere, my biggest client decided to leave, and I went from making more than $10,000 a month to not knowing where the money was going to come from. The plans I had made before leaving corporate life were not working.

From online courses to webinars, I tried all the different ways that other online entrepreneurs were using to make money, but none of them were working for me. Was it me? Did I not have the skills to make it happen?

Maybe I only possessed the entrepreneurial spirit and not the entrepreneurial capacity needed to be successful. I kept thinking, "Why are all the strategies that work for everyone else not working for me?"

3. Better Swallow Your Pride

When my biggest client and half my income decided that they could no longer afford me, I was shocked and scared. I had no idea how I was going to make money.

I searched Craigslist for part-time jobs, I went back to my old boss to see if he needed anything, and I even asked past podcast guests of mine to see if they were in need of marketing help.

I felt ashamed and embarrassed. Here I was with what many would say is a successful podcast, yet I’m trying to find work anywhere I can find it.

I asked another entrepreneur about how he felt when he had to go to an associate for work. He told me he wasn’t embarrassed at all and that you have to leave your emotions out of it and do what is best for the business.

4. Loss of Focus

When income isn’t steady, you tend to try everything, but trying everything means you are not great at anything.

I started doing things that were working for everyone else, from hosting webinars to creating online courses to writing a blog. However, I was not seeing the huge results that other entrepreneurs were experiencing.

I lost focus of what I knew I was good at -- app marketing. It was something that my audience told me that I was good at, but I didn’t think I was good at it.

The ironic thing is that I had clients who hired me for app marketing help even before I left my corporate job, but I resisted the agency route because I heard from others that you should not trade hours for dollars -- that agencies don’t scale. In short, I tried to be like other entrepreneurs instead of just writing my own entrepreneurial story.

5. Persistence is EVERYTHING

In his book, The Hard Thing About Hard Things, Ben Horowitz says that great entrepreneurs attribute their success to “never giving up”. After a rough 15 months full of self-doubt and often wanting to give up, I finally started to break through.

I was focused on building just one thing and saying no to everything else. And finally clients started coming to me.

Then in July 2015, 18 months into chasing my dream, I made $26,535.21 for the month. It was my first ever month of going over $20,000 and a monumental moment for me.

How did it all happen? I just didn’t give up.

Chasing your dream is a journey not a destination.

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