Embracing the possibility of ‘what’s next’ instead of ‘what if’

There are many articles which talk about how and why people leave their day jobs to pursue their dreams. It seems as though I read almost an article a week on the subject. Though there are common themes around what it's like to quit a perfectly good job where things are going right but you

Founder Friday is a weekly guest post written by a founder who is based in or hails from the Silicon Prairie. Each month, a topic relevant to startups is presented and founders share lessons learned or best practices utilized on that topic. May’s topic is leaving a full-time job to pursue a startup.

About the author: Jeff Slobotski is the co-founder of Silicon Prairie News.


There are many articles which talk about how and why people leave their day jobs to pursue their dreams. It seems as though I read almost an article a week on the subject. Though there are common themes around what it’s like to quit a perfectly good job where things are going right but you don’t feel like it’s where you’re supposed to be, I wanted to share some of my thoughts for this week’s Founder Friday post.

When I launched the idea for Silicon Prairie News almost four years ago, it started out as a side project that I was passionate about. I was intrigued by what was going on in the city after seeing other innovative communities and knew that our city had the same individuals doing amazing work here.

After holding events like BarCamp, Sarah Lacy’s book tour stop, a tweetup – yes, taking it way back when Twitter was just starting to become big – I saw a community taking root.

I remember sitting in my office in May 2008 talking with Danny Schreiber about what name I should select for a site to talk about the amazing things taking place in Omaha. The name you see today is the name which was decided on: Silicon Prairie News.

Ever since SPN’s official launch in July 2008 and teaming up with Dusty Davidson shortly thereafter, I’ve loved working on it.

I think one of the main ways you’ll know you’re ready to work on your side project is when you’ve worked on it, without pay even, for a considerable amount of time. Not days or weeks, but months. Month after month after month of putting time, energy and hustle and hours into what you enjoy building.

I love what Bo Fishback had to say in his post about when you know it’s time to leave your day job for a side project:

I don’t have any great examples of massive companies that were built in this mold (but again, I didn’t really look very hard), but lots of small and medium sized companies get launched this way. It’s one of the best ways to mitigate risk if there is something you love to do, but aren’t sure you could make a living doing it. What better way than to start getting paid for it to prove the market? And why not do this while keeping your day job?  

When SPN was started I didn’t set out to create a digital media company that included employees and more. My goal at the time, and true passion, was to start a blog, a vehicle that could highlight a community that was doing some amazing things, on more of an underground or undiscovered basis.

Months passed, and then years, and I could see from afar the momentum which was building. It was probably most likely at some point after we brought Danny Schreiber on board as our first full-time employee that I started thinking about the possibility of what could be. Could SPN be my startup? A full-fledged business and something that I could nurture along with a team?

It was November 2010 when I was wrestling pretty heavy with the decision to leave what at that point was a stable job, with benefits, etc. to pursue the dream of going 110 percent with SPN. One of the things that I kept coming back to was the fact that what was the worst that could happen? SPN would suddenly falter and fail – at which point, what then? I concluded that if SPN were to fail, the worst that would happen is that I would need to find another job … and life would go on. But, the most important thing is that I could look back at the end of my life with no regrets in wondering “what if?” What if I never went all in with SPN and the only thing I knew is that we threw some great events and hired an employee? That was something that I wasn’t comfortable living with – and once I fully embraced the possibilities of “what’s next” instead of “what if” I was ready to embark on the journey.

Before you quit your day job I recommend having the support and from your significant other, spouse or friend and confidant that supports your decision. Don’t go off on your own without running the idea by others whose input and advice you hold closely. At the end of the day you have to make the move that’s right for you, but knowing that you have those close to you to in support of your idea to jump on board full-time with your startup is something that can’t be taken lightly. I was blessed to have the support of my wife who probably knew much sooner than I did that pursuing SPN full-time was what I needed to do.

There’s a great piece from the Harvard Business Review titled “Great Businesses Don’t Start With a Plan” which basically says that the best business come from the heart – and through the founder’s passion – not through a perfectly composed business plan and idea, and that still holds true for me today.

The author Anthony Tjan says:

People feel a sense of accomplishment upon completing their plan, but what does that plan really get them? Filling worksheets can never replace zeroing in on the passion and purpose of your business. That Heart has to be there day one. The most researched business plan holds little value without a genuine Heart behind the idea and the Guts to just get it going.

SPN is now almost five years old, and I’ve been working on our startup full-time for almost a year and a half now. I’m still living. The “worst” I thought could happen hasn’t happened. With that, I don’t know what the final chapter of our startup will say, but I do know looking back, the point at which I decided to leave my full-time job was the best decision I made, and I’m excited to see what the next several years have in store for SPN.

If your heart is in it, and you’re passionate about the idea, there’s no better time to start than today. If not, you’ll look back many days from today and wonder “what if.”


Credits: Photo by Malone & Company / Big Omaha

About the author: Jeff Slobotski is the co-founder and chief community builder of Silicon Prairie News, an Omaha-based company dedicated to highlighting and supporting entrepreneurs and creatives, and an emerging model for grassroots entrepreneurial ecosystem development within the Omaha, Des Moines and Kansas City area. He is currently serving on the Greater Omaha Chamber of Commerce’s Board of Directors, was named one of Omaha’s Ten Outstanding Young Omahans by the Omaha Jaycees and received the Midlands Business Journal’s “Forty Under 40” award in 2010.

Slobotski can be found on Twitter, @slobotski.


 Founder Friday is brought to you by the Heartland Technology Alliance

Thanks to our Founder Friday series sponsor, Heartland Technology Alliance, a nonprofit working as an advocate for innovation and competition in technology and communications across much of the Silicon Prairie and throughout the Upper Midwest.


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