Drafting Failure: Lessons in Business Planning
4 Feb
But caligater, didn’t you just write about Failing with Finesse?! Yes, yes I did. I was prompted and inspired by Jason Markow’s latest Think (here) project to write more about my failures. His project, FAILweek, is an event “designed to showcase and celebrate failure.”
Visit Welcome to #FAILweek for an intro to Jason’s project. Think (here) is where it’s at.
I failed at writing the first draft of my business plan.
Two things are (potentially) annoying to some of you in this statement:
- To some, business plans are worthless exercises in shuffling paper and creating vapid, useless documents for potential investors and venture capitalists.
- If it’s a first draft, who cares if it’s a failure?
I’ll respond to these two annoyances in just a moment. But first: the stage, fireball and lessons of this failure.
The Stage
In my Master of Social Science program, I had the opportunity to take the course Business Plan Writing for Social Entrepreneurs. The end product was going to be the real deal—not an outline, not an executive summary—a business plan. My academic work would launch me into my career after grad school.
Guided by an excellent instructor and surrounded by experienced and driven classmates, I began the semester knowing I was set up to hit my plan out of the park.
I rode on my excitement and intellectual momentum for the first two months of the semester. I already had quite a bit of initial marketplace research and competitive analysis completed, as the business plan I was writing was born several months earlier. I had inertia to dive headfirst into the plan. And dive I did.
The Fireball
Simultaneously, my non-school life began to take new shape (in fact, I was conscientiously changing that life-shape when I quit my good job and simplified my priorities). Although my decisions were meant to give me unbridled time to focus on school, so much disruption in my life actually took away focus on my schoolwork.
I lost momentum. Although I reprioritized my responsibilities, it happened too late in the semester. I struggled to complete the business plan—including scrutinizing cost models and how to make my business profitable; fleshing out my marketing plan based on that cost model; and exploring the best organizational structure. {HELLO—the critical parts of the plan!}
I realized I wasn’t going to hit my business plan out of the park. In fact, I knew that it was going to be disjointed and weak.
I grudgingly turned in my plan, deeply ashamed that it wasn’t my best work. And as fair and supportive as my instructor was, I received the grade I had earned. It wasn’t a good grade.
I actually cried.
The Lessons
The poor grade meant that I had disappointed my instructor and myself. It meant I had failed at creating a piece of work important to my future (and beyond the grade or the class). Though not all of the factors that contributed to my failure in drafting a business plan could easily have been changed, there were some areas for improvement. Next draft I’m going to remember some of my lessons of failure:
- Make use of resources – I was surrounded by really smart people in my class. And if I had asked, I imagine several of them would have helped me. Duh!
- Aim for consistency – I should have set aside 3+ hours each and every weekday to work on the plan. At least.
- Be (mentally) prepared for obstacles – I spent the semester reading/talking/hearing about the need for entrepreneurs to be ready for unanticipated consequences. I didn’t consider that I would encounter obstacles while writing the plan. Low and behold—the plan-writing is part of the entrepreneurial process! Duh x 2!
…Back to the two annoying things:
1) For me, a business plan is a framework, a way to organize my thinking, prepare, mitigate risks, and build an intellectual—and tangible—launching pad. I’m not writing my plan for a venture capitalist. I’m writing it for me.
2) The failure of my first draft was like getting sucker punched as soon as I stepped into the ring. I’m going to get back up, but that first blow did sting.
The entrepreneurial horizon looks expansive and fertile from where I’m standing. As much as I drafted failure, I am moving forward in drafting success.


