The Side Hustle and Flow Interview Series: Willie Jackson

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Last week, I kicked off a new series on the blog called Side Hustle and Flow, which profiles people who had full-time corporate jobs and worked on their side business until they were able to quit and do it full-time. Chandoo was the first person profiled, for parlaying his love for Excel into a full-time, thriving business.

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Today I am thrilled to introduce you to Willie Jackson, a good friend and future collaborator (we are doing a college speaking tour about the new world of work).  From the first time I met Willie in person on my Atlanta book tour, I knew he was special. He is in his mid-twenties, but carries himself like someone much older and wiser. He is not only talented in his technical field, but is a natural businessperson. And he is already starting to mentor and encourage others, like Chris Jordan, a former insurance agent who is now doing web design.

Willie perfectly illustrates the shift in the employment paradigm, cemented on by the massive economic collapse in 2009. Talented young people are increasingly bypassing corporate careers to go straight to work for themselves. They are not willing to put up with corporate politics and decades of “paying dues” to get a big payoff. This will alter the way we recruit and manage young employees and force us to leave mafia culture behind. Here is Willie’s story:

What was your former day job?

IT Consultant with Accenture.

What was your side hustle?

Web Consulting (Design, development, hosting, and marketing.)

When did you start working on it?

I billed my first client in the Summer of 2007.

Did you tell your employer you were working on a side project? Why or why not?

Nope. I never felt the inclination to share, largely because it had no impact on my job. Consulting is not typical employment; my “boss” changed with every project and so long as I did what I needed to do, no one cared what I did with my free time.

How did you know when it was time to quit your day job?

Panic attacks after a particularly unpleasant week were a pretty clear indicator that something needed to change. Mind you, I’m one of the most laid-back humans you’ll ever come across. There was a pretty disastrous and awkward event that lead to this back-of-camel-breaking straw, but we’ll have to leave that for a different blog post 🙂

It’s important to note that I always had entrepreneurial aspirations; I just didn’t know what I wanted to do. Spending three years in an unfulfilling job was a great way to figure out one thing I didn’t want to do, though. #optimism

What scared you about that decision?

Nothing. I had no fear.

Actually…

I feared giving 15-20 years of my life, three failed marriages, and countless hours to a faceless behemoth. I feared waking up five years later still wanting to quit. I feared not showing my younger sister and mentors that anything is possible. I feared giving the best hours of the every weekday during the best years of my life…without ever having the chance to live a life worth leading.

How did it turn out?

I’m roughly six months out and happier than I ever was in my old position. My business is growing, I have more time for “passion projects,” and my story has inspired others to either a) realize that they, too can move courageously toward their dreams or b) put a more finite time line around their exit strategy.

What are you doing now?

Enjoying a life without limits. Spending more time reading. Learning the finer points about running a profitable business. Preparing to launch a new business. Developing deeper relationships with my friends and family. Observing the beautiful synchronicity of it all. Eating gummi bears.

What advice would you give for others who are working on a side hustle now that you have a bit of distance?

Move faster. Stay hungry. Life is too short and the world is waiting on your gift!

How can people find you, or hire you?

On the internets:

http://williejackson.com

Thanks Willie! I expect great things from you. And I know you won’t disappoint.

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20 Responses to “The Side Hustle and Flow Interview Series: Willie Jackson”

  1. Ramona says:

    Reading a story that happened in such close proximity feels like being on the sidwalk as your friendly neighborhood Spiderman swings by waving at you personally lol. Way to go Willie! I’m 25 and can NOT very easily recover from any financial setback I’ll incur over the next five years. With 2 small children, a mortgage, a husband, mounting debt, an unbearable job and no clear passion or gifting, the leap you made looks more like a suicide mission to me. But it helps to see that things are shaking up in the neighborhood. Makes me feel as though if the after shocks don’t propel me, then maybe desperation will lead to enough clarity to create my own earthquake.

  2. […] recently chosen by Seth Godin to work on The Domino Project. Willie was also featured in my side hustle and flow series earlier this […]

  3. Great interview Willie!! I feel inspired and really appreciate your candor about what was going on for you and your fears about taking the leap.

    I can’t wait to eat more gummi bears:). I love gummi bears.

  4. […] far we have profiled Chandoo, Willie Jackson and Dan […]

  5. […] Last week, I kicked off a new series on the blog called Side Hustle and Flow, which profiles people who had full-time corporate jobs and worked on their side business until they were able to quit and do it full-time. Chandoo was the first person profiled, for parlaying his love for Excel into a full-time, […] Original post […]

  6. Fred says:

    Very interesting story Willie. I liked your last comment where you said, “I could not have survived in my former job for too much longer.” That is the most dangerous thing about a side hustle. Often time, once you experience the satisfaction of building a business, it is hard to not want to do it full-time.

  7. You’re very kind, Usama. I think you give me too much credit, though. What this interview doesn’t tell you is that I could not have survived in my former job for too much longer. It crushed my spirit, creativity, and motivation in many ways.

    So I had to get out. Thankfully the net appeared 😉

    • I’m in a similar situation: my photography “side hustle” is my passion and my day job is literally killing me — I’ve always had a bit of depression, but it’s blown up in the last 18 months of this job (that I’ve held for 5 years) with panic attacks, completely wasted days incapacitated, and I now have FMLA clearance for time off from the day job for major unipolar depression and anxiety.

      I guess my question is, while I know physically the job is killing me, I’m not making nearly enough to survive on in the side hustle to leave the day job, as far as I’m concerned. Did you know you’d financially thrive when you left your job, or was it a “I might make it, I might not, but I need to leave NOW for my health and sanity!” decision?

      • Moreso the latter. I’m 25 and can very easily recover from any financial setback I’ll incur over the next five years. I don’t fear failure or being broke—those are temporary.

        Your health and sanity can’t be replaced once they’re gone however, and I’d encourage you to at least begin looking for other places of employment while you build your side hustle revenue. It pains me to hear the suffering you’re going through.

        Be encouraged; the water’s fine on the other side.

  8. Usama says:

    Pretty Amazing story. Only if everyone has the courage of what you did. Follow your heart and live your life as you want.
    Thanks.

  9. What a great story! Kudos to Willie for jumping when he did. This sentence in particular resonated with me “I feared waking up five years later still wanting to quit”.

    I just resigned from a company after 7 years to work full-time at freelance writing, which I have been doing on the side for 6 months. I am counting down till my last day of work when I can dive headfirst into my business and really start making it grow!

  10. I can relate to your previous situation Willie, I’m just going through that, thanks a lot for sharing your fears! This really gives me an insight that I wasn’t looking before.

  11. Thanks for featuring me, Pam. It goes without saying that your work—specifically, this blog—was a catalyzing force in my life as I prepared for launch.

    So thanks 🙂

  12. I spent 20 years working for “The Man” and I certainly don’t regret it, because it gave me such a range of experience and led me to my ultimate path. The last part of my career, I did a lot of work with HR departments on workplace culture and so on. There is most definitely a new attitude toward career these days and I am glad that being your own boss is a more accessible choice than it used to be. With the internet and technology now it is relatively simple to start a new business full time or on the side and many more of us are making the choice the be “corporate fugitives”. It isn’t for everyone, but it’s everything for some! Thanks Willie for sharing your story.

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