How do you prepare for failure? It makes sense to have a Plan B, like a nest egg you can crack if it all goes south, or a set vocation that you know is in demand, or perhaps an alternative business you can launch. Only the most risk-tolerent - and, perhaps, reckless - of us go into an endeavor without any type of security. In fact, it may be more motivation for you.

Now, how do you prepare for success? I've found that most of us have made peace with failing, but actually don't have a plan for when we succeed. 

In 2014, I co-founded the social meetup app Cuddlr with a couple other people - super small operation with barely a budget. I spearheaded the launch strategy and mapped out our plan from pre-launch to about 6 months out. My co-founders expected a cult following, I expected a more mainstream opportunity. What we got was a smash hit, getting an incredible amount of press and running to the top of the Apple App store within its first week. We're lucky we had a framework plan for post-launch, but it was difficult to ride the rocket ship even with that. Imagine if we had no plan for success! We probably wouldn't have been acquired.

The challenge for me and my co-founders, as well as many entrepreneurs, was that our focus was on evangelizing our service. But what if people love our service? It becomes preaching to the choir. There has to be a strategy if you actually win. It's akin to a presidential candidate being focused on the debates, but not having a set plan for when she actually gets into office. It's a recipe for disaster - even though you got what you wanted.

Here is some food for thought:

Plan it all the way through: What if you get that gold-star client or make that financial goal this year? Consider the next goal you have in mind. For instance, what kind of maintenance will be required to keep that hard-to-get client? Or how, exactly, will you be using that additional profit from a financial milestone? 

Line up your mentors: A fresh success often means dealing with new issues that require a brand new strategy. Do you have a brain trust ready? The key isn't to have people who know what you know, but know what you'll need to know once you succeed. Again, planning for success means you assume you'll need a higher level of insight.

Look at different types of success: Entrepreneurs like myself often have many opportunities happening all at different stages, which means you may reach your goal with two medium-sized clients versus the big whale you've been trying to score. Does that affect the outcome? Run through a few ways success could happen for you. You may be surprised at how a slightly different outcome will affect your post-success strategy.

Published on: Feb 26, 2016