The Plan

The plan is an essential piece of our entrepreneurial pursuit. Not creating one is a recipe for disaster. Over-engineering one may lead to analysis paralysis. Finding the right balance of knowing when “good is enough” should guide our roadmap. Most importantly, we need to be honest with ourselves when the time comes.

In earnest, the entrepreneurial route was something that I had put on the back burner. Sure, I had been fascinated by entrepreneurship for a while; I concentrated in entrepreneurship during my MBA studies, co-founded a mobile app startup called Frienso, and have been a voracious reader of TechCrunch and Crunchbase. On occasion I found myself daydreaming and brainstorming business ventures, and then chatting up anyone who would listen. While the drive to take action coursed through my veins, I still wanted to give the corporate world an honest go.

After some deliberation, I took a much-needed weekend trip to San Francisco for the 4^th of July. It can’t be underestimated how much that trip served as a game changer.

Maybe there was something in the water, but San Francisco brought the reality of the tech startup scene front and center. I noticed that people seemed happier. They took risks. They wanted to make a difference in the world. All of this energy and passion, and they didn’t seem overly concerned about money despite the cramped living conditions and a higher cost of living. Seeing this firsthand, I felt calm and emboldened!

Even though I was motivated to take next steps, I knew there was a big difference between talking the talk and walking the walk. A slew of unknowns raced through my mind. Would I stay in Chicago? Would I try to launch something on the side and keep working full time? What business would I launch? Would I be a sole founder or recruit others? Did I have enough technical skills? The questions seemed endless.

After taking a hard look at all I had worked for and my station in life, I decided it was time to push the “reset” button. The corporate job had to go, and I felt a strong urge to move out West. San Francisco, Seattle, and Denver all seemed like great options!

As a step in the transition, I decided that a Coding Bootcamp would be a good idea since my passion is in early stage web and mobile software. A sharper technical skill set is something I value. While these schools can be costly, 5 months of dedicated programming training in Denver quickly became a very appealing option. I found a veteran-friendly program called Skill Distillery that focuses on full-stack web development. After a little research and touching base with the school’s faculty, I knew it would be a great fit!

The transition time and additional training are two points that I plan to take full advantage of. In the months to come I will develop technical skills, network, and seek out co-founding opportunities. While this is all a gamble, it is one I am taking on with open arms.

Know that part of being ambitious and taking risks involves taking action. Execution of our entrepreneurial transition plans should rank just as high on the priority list as the actual execution of our start-ups.

In many of our lives there will never be a perfect time or a perfect opportunity. Life is full of tough decisions. As messy and complicated as it can be, we have to decide what makes the most sense for us. There will be no shortage of people who ask us to reconsider, but if we are steadfast, we can carve out a path that mitigates risk and offers great opportunity.

How then can we apply this example to our own lives? Everyone’s plan will look a little different. The first step is to define what you want in your pursuit.

Since we all have different ambitions, talents, family obligations, financial situations, relationships, responsibilities, and personal needs, we have to prioritize them and determine how they can be adequately addressed in the transition.

Do we need to have a tough conversation with our loved one? Make it to another validation milestone with the business endeavor we are currently working on? Set aside more money? Figure out healthcare options? Relocate? Build out our professional network? Develop a new skill set? Rebrand ourselves? Sell or rent out the apartment? Get rid of furniture?

Write these things down and figure out what threshold needs to be met before you too can take the leap. Set reasonable times and guidelines for achieving these thresholds. Overall, knowing that our affairs are in order gives us a level of comfort and confidence that we can do this. Accept that this isn’t going to be easy, and that there will be a rollercoaster ahead. Our plan will likely change, but at least we had one to begin with.

We are playing the long game, and we shouldn’t put too much pressure on ourselves to start the next unicorn company. Success comes in all shapes and sizes. Sound planning and persistence will get us there.

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