Why I Hate Maggie, and her “Start with the End in Mind” Message

Why I Hate Maggie, and her “Start with the End in Mind” Message

I just got off my first phone call with “Maggie the consultant” and I have three immediate impressions.

  • Maggie’s smarter than me. 
  • I like her.
  • I also hate her a little bit.

Maggie strikes me as incredibly organized and intentional.  Primarily a corporate background, she also has a successful small business under her belt.  She’s one of those people that sounds very sincere when she say’s “start with the end in mind”, because she wants new business owners to start their business with a clear plan for how they’ll exit it.  That’s what she did with her small business, and she means it when she says it to others.

This puts me in a horrible dilemma. 

I love the advice. 

It’s wise. 

It’s logical. 

And I can’t conceive of following it.

I’m really conflicted here.  The advice makes perfect sense, but it runs completely counter to my life experience.  Maggie’s not the only one who gives this advice.  There is an entire exit planning industry that would love all new business owners to fall in love with the phrase “start with the end in mind”.

But when they say it, I can’t help but feel that they are out of touch with what it means for most of us to start a business.  When they say, “start with the end in mind”, it feels like they see the choice of starting a business as a logical, reasonably considered, thoughtfully executed process.

When for many of us, starting a business isn’t an act of careful execution – it’s an act of exorcism.

The “Start with the End in Mind” Crowd Wants Me To

Sit calmly and contemplate my anticipated business journey.

See the potential options that lay ahead.

Map out the path.  Define the end.  And start.

With that end in mind.

“Have a nice walk, honey.”

For Me It’s Always Been More Like

Sit calmly and contemplate my anticipated business journey.

Flip out when I realize how likely failure is and try to ignore the business idea for as long as I can.

Find out I can’t get the business out of my head.

Fight the butterflies in my stomach.

Step to the cliff’s edge.  Look down.  Look back several times. 

Hesitate.  Second-guess. Delay.   

“Oh, crap what’s going to happen.”


Contemplate the end?  Ha!  I’m just trying not to pass out from sheer panic.

Makes me sound super cool, right?  My start-up truth hasn’t been cool.  It’s been an ugly, anxiety fueled wrestling match between my doubt and my drive.

I’ve started 4 businesses from scratch and purchased 2 others.  I’ve been lucky enough to have several successful exits (with a failure or two thrown in to keep me humble.) 

My new start-up is in the “exit your business” space, and I’m consuming a lot of content from exit planners right now.  Over and over they tell me to “start with the end in mind”, and it just doesn’t make sense.

How it Feels at the Start

In the last 60 seconds I’ve felt frustrated, excited, discouraged and wildly optimistic.  In a word: messy.

That’s the start of the blog post from five months ago when I started my business.

Does it trouble you to hear a business owner voice apprehension, doubt and concern?   Then you’ve never spent much time around business owners.  Doubt is a truth of this life.   At least it’s always been for me.

My hope at the time, and currently, is that this new thing will be wildly successful and consume me professionally for the next decade or two.  I’m optimistic based on how things are going, but I’m also aware that it’s 50/50 that I’ll have to quietly wrap it up 36 months from now.  If that happens, I need to come up with an explanation that doesn’t include the words “catastrophic failure”.

Now, I can hear the “you’re never going to succeed with that kind of attitude” calls through my computer screen as I write this.  But I’ll politely say, save them for someone with less faith. 

Starting is an Act of Faith

Every business I’ve started from scratch was ultimately an act of faith.  Part ritual and part therapeutic extraction.  I was driven by a desire to do a thing and was finally able to generate enough belief to try and make it happen.  These start-ups were acts of faith, not acts of calculated capitalism.

In most cases I put off starting until it became clear that my choice was either to do the thing or whither from the regret of not doing it. 

My wife will tell you I’m one of the most methodical thinkers you’ll meet, but when it comes to my start-ups, it wasn’t about making a planned, “consider the end” decision to go or no.   It was about built-up desire momentarily overcoming my fear. 

I’ve always loved Michael Gerber’s description of the “entrepreneurial seizure” that creates the start of most businesses.

Inside your mind it sounded something like this; “what am I doing this for?  Why am I working for this guy?  Hell, I know as much about this business as he does.  If it weren’t for me, he wouldn’t have a business.  Any dummy can run a business. . .Once you were stricken with an Entrepreneurial Seizure, there was no relief.  You couldn’t get rid of it.  You had to start your own business.

The E-Myth Revisited, page 12

Oh, and by the way, while you’re having that seizure, keep the end in mind.

I’ve Found it Easier to Buy with the End in Mind.

I’ve started twice with the end in mind, but both times with businesses I purchased.  I was shopping for businesses I thought I could turn-around and sell within 3-5 years.  It was primarily a mental exercise, an investment equation, all driven by targeted outcomes – and the end was very much in mind at the start.

These were decisions, but my start-ups were about desire.

And this is where I think the “start with the end in mind” mind-set can really go off the rails.

Why They Say It

When exit planners beg business owners to “start with the end in mind” they do so with good intentions and for good reasons.  They want you to avoid the pain they’ve seen other business owners experience.

Most exit planners have tried to help owners through difficult and discouraging situations.  Situations where some simple forethought might have made all the difference. 

The business owner is burnt-out, discouraged and finally ready to exit their business.  But it’s the first time they’ve given an exit more than a passing thought, and now it’s all they think about.  Then they quickly discover that their business is unsellable.

If only they had thought ahead!

It’s a painful place to find yourself as a business owner.  And it’s hard to try to help the owner as a consultant

When you see the pain and destruction of poor planning, starting with the end in mind makes real sense.  It’s wise and incredibly beneficial.

And if the argument was “hey, Bozo, take a minute before you start and consider that you’re not going to want to do this forever” I’d be all for it.  Some planners do that, but the problem is that too many don’t stop there.  They send out things like this:

When Should I Develop My Exit Plan? 

1. You should begin your exit plan when you start your business. 

2. The first part of the exit plan is growing a profitable business that would be attractive to potential buyers or new owners. 

3. You must grow a profitable business from day one and then you are always able to exit your business. 

“Grow a profitable business from day one”, who is this guy? 

Has he ever started a business?  How big is the silver spoon in his mouth?  Has he ever had to decide between paying the minimum balance on the credit card or buying more paper for the printer?

Has he ever made mistake after mistake as he learns his way through a new thing?

Has he ever worked a full-time job and then done another eight hours working on the business he wants to start?  Profitable from day one?

This sort of message drives me crazy.  It’s so robotic, so mechanical, so “corporate clean” and so disconnected from the real choices most aspiring business owners face.   It’s a very broken “start with the end in mind” adaptation, and so very, very discouraging to someone starting out.

Running with Baby Sharks

Between business ownership gigs I took the opportunity to work for three years helping aspiring entrepreneurs start new businesses.  It was a fabulous adventure.  Every day was populated with people who had an overabundance of ideas and energy, and a lack of experience and know-how.

With rare exception, each had a mountain of learning to do and overwhelming challenges to face.  The primary assets they had were the energy and enthusiasm generated by their blind optimism, their passion for their idea, and their desire for business ownership.

Because of what they lacked most of their decisions were made under the gun, with too little time, too little money, and too many options.  They did the best they could each day and started the next day eager to make a little more progress.

They knew failure was a likely outcome.  They knew the path between their start and financial stability was a rough and unclear one.  They moved forward anyways.  Pivoting, evolving and exploring.

Dealing with them was energizing and exhausting – and unquestionably inspiring. 

Those starter-uppers inspired me, and I’m back in a start-up.  I have a vague idea how this might end, but I also know that odds say failure is likely.

So again, it’s messy, but it’s real.

The Exit Planners are Right, But Some Aren’t Good at Capitalization

An exit plan can be of huge value to a business owner interested in a successful exit.  And without question, most business owners wait way, way, WAY too long to start the exit planning process. 

Most business owners won’t plan for their exit.  Almost all will regret it.

I believe in exit planning.  If you want to sell your business, you need to intentionally build, design and manage that business with your exit in mind.  The sale of your business will not happen by accident.

And if you’re like Maggie, and can do it from the start, more power to you.  But here’s where I think some in that crowd get it wrong. 

The message shouldn’t be START WITH THE END IN MIND

It should be START with the end in mind.  Oh, and leave out the “grow a profitable business from day one” stuff.  It just makes you look pretentious and silly.

Just Start

If you can’t see the end, you should start anyways. Do it.  Get going.  Don’t wait.

Not sure where it’s going to end?  Join the crowd.  If you’re like me, thinking about “how it will end” leads to repeatedly Googling “what percent of start-ups end in failure”.  If you have an end in mind, fabulous, if you don’t then start anyways. Don’t kill your desire because you don’t know where this is going to go.

And then, as soon as you can, start thinking about the end.  Your desire to exit will almost certainly sneak up on you.  The sooner you start thinking about it, the better chance you have at a successful exit. 

By the way, I don’t hate Maggie because she wants small business owners to “start with the end in mind”.  It’s wise advice, especially when the advice is delivered as thoughtfully and reasonably as Maggie does it.  

No, that’s not why I hate Maggie. 

I hate Maggie because she’s smarter than me.

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(1) “Begin with the End in Mind” – attributable to Stephen Covey’s Habit #2 from the book, 7 Habits of Highly Effective People (originally published 1989)

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