The Life-Altering Power of a Bad Plan

Hello Dear Friend,

Welcome to Things I Wish I Knew Earlier, Sunday!

Moving forward, I will include the prefix “TIWIKE” in the subject line for each newsletter to help readers distinguish it from other emails. It stands for Things I Wish I Knew Earlier, which I hope is obvious.

Anyway, here are three ideas on the life-altering power of a bad plan for you to consider in the coming week.


TIWIKE #1: A Bad Plan is Better than No Plan

December 7th, 2017 was the scariest day of my professional life.

I was seven months into building a business as a real estate agent. Up to that time, I had earned $1500…for the entire year. Working my ass off six and seven days a week, earnestly giving my best effort to get this business up and off the ground, had yielded next to no results. Credit card minimums were mounting.

But I had a deal closing the following day, which would buy me enough time to get past the holidays.

Then I got “the call.” My client reached out in the evening to let me know that, after lots of prayer, she just didn’t think she needed to buy that property. I was devastated.

I found myself face-to-face with what I believe is the greatest problem for every aspiring entrepreneur: Directionlessness, lack of clarity on where to go and how to get there.

I had no idea what to do. Could it be possible I had invested a year of my life into a venture I couldn’t figure out? If I didn’t make this work, what else would I do?

Just when I thought the situation was too much for me to handle, I saw a glimmer of hope.

I found out about ​Doctor Jordan Peterson’s Self-Authoring Suite​. From the website, “The Self-Authoring Suite is a series of online writing programs that collectively help you explore your past, present and future.” At that time, I had been journaling consistently for more than five years, so my past and present were thoroughly explored.

But the ​Future Authoring Program​ changed my life forever.

It’s broken into two sections that are meant to be completed on two separate days.

The first day is for general vision casting. You are prompted to write about your ideal professional life, social life, and family life in broad strokes. Then on the second day you distill the prior day’s writing into 6-8 goals.

And I did it in classic me fashion. I created a massive, intricate, 10-year plan.

It was terrible, but it was the best I could make at the time.

The idea was to continue working to sell real estate until I earned enough money to move out of the trailer on my family’s property into my own place in Birmingham. Then I was going to quit real estate, get a job at UAB (the local university), and have them pay for my education to become a clinical psychologist.

This vision gave me the faith and confidence I needed to keep working at real estate despite the lack of success.

In January, I made $3500.

In February, I made $14,000, which was an unbelievable sum at the time. I legitimately didn’t know it was possible to make that much money in a month. “Maybe this whole real estate thing will work out,” I thought.

This taught me a lesson I’ve never forgotten:

A bad plan is better than no plan.

TIWIKE #2: Bad Plans Can Become Better Plans

The outcomes in your business and life reflect the quality of your plan.

After earning more than $25,000 in the first three months of 2018, I let go of the idea that I would become a clinical psychologist. I redid the Future Authoring Program, which resulted in a far better plan than I made the previous December. All I had to do was strip away the elements of the first plan that no longer applied and fill the gaps.

The 2.0 version of my plan led to earning $130,000 in 2018, a sum many times greater than I had ever made.

I turned my bad plan into a better plan that lead to better outcomes.

That’s how this works. Better plans create better outcomes. Once you muster the courage to make a bad plan, you earn the right to iterate it into a better plan. If you continue this iteration process over months and years, then you create better and better plans, which inevitably lead to better and better outcomes in your life.

This illustrates one of the best aspects of a bad plan:

After executing a bad plan for a while, all the reasons why it is a bad plan become obvious, so you can update the plan reflecting all you learn.

In this way, bad plans can become better plans.

TIWIKE #3: Anything Worth Doing is Worth Doing Badly…at First

The truth is that when you start something new, you don’t yet know the majority of what you need to know to make a good plan.

Building a business is a creative, open-ended endeavor. There are a million ways to do it well. It’s messy. Progress is not linear. And the big secret that all successful business owners know is that perfection is impossible.

So what alternative to making a bad plan do you really have? I don’t see any, other than having no plan at all. This speaks to what I believe is the second biggest problem all aspiring entrepreneurs inevitably face: Perfectionism.

Yet fear of imperfection has killed far more business ideas than imperfect action.

In fact, I think imperfect action is the genesis of every successful business.

More broadly, this is how all skills work. When you start, you aren’t very good. With a considerable amount of time and effort, you begin to suck less. And with a ton more time and effort, you start to get good. This is the standard arc that leads toward mastery in all things.

Building a business is a skill that you likely won’t be good at without practice.

As an aspiring entrepreneur, trying to build a business is the thing that’s worth doing badly.

That means bad plan + imperfect action.

Anything worth doing is worth doing badly…at first.

The Bad Plan Challenge-Create Your First Bad Plan

The Future Authoring Program helped me overcome my lack of direction by making a bad plan, but it left me wanting more in several ways.

  1. It was not designed for aspiring business owners, so I received no guidance on building a business plan.
  2. It was completed in isolation, so there was no way to get feedback from peers.
  3. It wasn’t in-depth enough, so the plan ended up being too vague.
  4. It produced a flat, static PDF print out that was hard to update and iterate. I wanted a living map that I could update and improve over time.

I’ve been working on a project to build the experience I wish I would have gotten from Future Authoring.

It is still very early in the developmental process, but here is the description I have so far:

  • The Bad Plan Challenge is a 28-day, cohort-style challenge that helps aspiring entrepreneurs develop a written roadmap—a Bad Plan—for their business and life alongside peers.
  • The central deliverable is a Bad Plan Dashboard in ​an incredible information management system called Notion​ that will become a living hub for your life that will transform and grow and change with you from then on, if you want to use it in that way.

Here is a set of screenshots of my personal dashboard to get a sense for what yours will look like.

Problems Solved:

  1. Directionlessness- #1 problem for aspiring entrepreneurs
  2. Perfectionism- #2 problem for aspiring entrepreneurs

Total Time Commitment: 15.5 hours over 28 Days

  • .5 hours for kick off event
  • 2 hours for awards ceremony
  • 4 hours of weekly group masterminds
  • 7 hours of total writing (15 minutes per day)
  • 2 hours of weekly reflections to extract ideas (30 minutes per week)

The Opportunity

I’m in the process of filling the first cohort ever for the Bad Plan Challenge.

I’m calling it the beta cohort because it will be filled with good friends will tell me the truth. What I need more than anything is feedback on how to iterate and optimize the experience for participants. This is in preparation for an official launch for the first alpha cohort in March of next year.

So far I have 8 commitments. I hope to bring together 24 participants inside the beta cohort and no more. It will begin on the first Monday of October and run exactly four weeks.

If you are interested in learning more about joining this beta cohort, reply to this email, and we can set up a time to discuss the details.

Scroll to Top