Instead of the Perfect Plan, Build a Successful Business Structure Or What Sailing Taught Me About Business Planning

I love the old adage, “life is what happens while you’re busy planning.” We live in a culture full of planning addicts. We love to think that we can control everything and everyone around us, so we try really hard to do just that. But here’s the thing: if there is too much focus on business planning, then exactly when do we have time to be productive with what’s actually happening?


Game plans. Business plans. Financial plans. Personal plans. Short-term and long-term planning. Goals to attain this, Steps to move forward on that. Processes, procedures, budgets, operations…there are entire departments within large corporations whose primary function it is to plan.

Don’t get me wrong; it’s thrilling that there are people devoting entire careers to doing this and doing it well (it’s especially thrilling for people like me with planning-itis). We all need plans and processes and procedures to stay organized. But what about the inevitable times in business (or life) when stuff just doesn’t go the way we plan?

And honestly, how often do things actually go according to an exact plan? How much time is wasted overplanning and underproducing? And what happens when the plan in place is no longer valid, is outdated, or the shit hits the fan?

Yep, organization is a key element to productivity and anyone’s capacity to focus. It’s the way we as humans are programmed to operate. But, NEWS FLASH: Plans go awry! Stock markets crash, business deals break down, turnover occurs, stuff changes in ways that no one can predict, and timing becomes quite an issue.

Is there a way, then, that we could actually PLAN for the unexpected to occur? And exactly how would we do that? Well, I’ve got some thoughts about business planning to share.

Business Planning for the Unexpected

It’s always a good idea in business planning to be a bit risk-averse. We don’t want to waste resources on extreme ideas that are more likely to fail than succeed. But it’s also true that some of the greatest risks yield the greatest rewards.

If only we could predict which risks would pay off. This is what our brains crave. After all, planning is a function of the frontal lobe of the brain, which being at the front of the head, fittingly pushes out into the world of distractions and projections.

In other words, planning, including business planning, is inherently distracting.

This week, I’m living out this lesson. I’m visiting my parents, who recently bought a 40-something-foot sailboat, which they keep on Lake Michigan. And the trip has really got me thinking hard about this business planning stuff. As a small business owner, work doesn’t just go away when I want to take a vacation. So, of course, I have deadlines this week and I have to fit the work around other people’s plans (fortunately, my intermittent insomnia is making this more doable).

Also, taking a vacation on a sailboat is pretty much the opposite of planning. We can’t plan which port we’ll land in for the night because we can’t predict the wind speed during the day (even with the fancy wind-catcher device on board, we’ve been mostly just drifting and looking for wind today). I can’t plan to post my blog tonight when we get into whichever port we reach (assuming we actually make it back to shore before midnight) because I can’t predict whether the Wi-Fi in the marina will be reliable (there’s in fact, no Wi-Fi at this marina, which is why I’m posting this now). So, I just have to let all of that go.

I won’t lie and say it has been easy for me to avoid planning my days around my work, but it definitely has made me more focused on my work when the opportunities reveal themselves. We love to spend a lot of time hanging out in the future, instead of being engaged with what we’re doing right here and now.

But at any moment, if we are distracted, the rug can be pulled out from under us and that can be especially damaging for small businesses and startups. So, rather than being tempted to plan every move down to the penny, plan to have your plans unexpectedly interrupted.

What does a successful plan look like?

You can probably guess that a successful plan isn’t the perfect business plan you submit to investors. Sometimes successful business planning amounts to being ready to grit your teeth and accept the inevitable slow periods. It means having the attitude to forge ahead when a plan “fails.”

Ups and downs happen and it’s just one of those “risky” things that become a way of life for small (or big) business owners. If you want to feel better about the risks you’re undertaking in your business, consider stock market traders.

Day traders are some of the best in the world at making good decisions based on what’s going on right now and rolling with it no matter the consequences. They know that the game is more about moving with the speed of business than trying to control it. Interestingly, with the ability and capacity (yes, it’s definitely a capacity thing!) to move in real time naturally comes the power to control it much more.

The fantastic thing about these stock market gurus is that they are well researched, trained, and knowledgeable. They understand the ins and outs of their industry, the trends, and all of the calculations and ways to measure these things. They master the concepts of their trade and apply these concepts on a moment-by-moment basis, knowing that the only planning that can truly be done in a successful business is understanding the variables.

In essence, we can be more efficient in our efforts in business if we are actively engaged with a structure that we’ve created for ourselves within which to work. This is what owning and operating a business is all about: we build the field, make the rules, and play our own game to the best of our abilities. In this way, we are much more in control of business and ourselves. We know when to push and when to pull back; when to spend and when to save; when to hire and when to fire; and we can almost predict when it all will happen.


How about instead of making a plan, we build a successful structure?

You know, a structure full of the real important stuff, like offering high quality products or services so as to ensure that everything that can be controlled is indeed controlled. Be good at what you do, market it to the best of your ability, and then be patient.

Marketing and pushing out campaigns and the timing of carrying out logistics is vital to the health of any growing business. Day traders have special rules for this: buy low, sell high. In other words, there are going to be highs and lows, ebbs and flows. Flow when it’s flowing, pull back when it’s ebbing.

Here are some expert-planner tips on building, being, and staying on top of your own game:

1. Be really good at something. This is a no brainer. You wouldn’t be where you are if you weren’t good at it. Now, go forth and build a structure around that.

2. Have a rough business plan. I’ve been working on my business planning for months now and I’ve been in business for more than a year. Had I tried to write the business plan first, I honestly believe I would have never started my business. This is because I wouldn’t have realized before I was running my business that a business plan is an ever-evolving document. I would have wasted tons of time trying to predict unknown variables and creating the “perfect” plan.

3. Hire really good people — contractors or employees (If you’re looking for great content marketer, I can totally hook you up!). Hire people that are efficient, that care, that are interested in quality, and that feel good about the role they’re playing. It’s all part of making sure your business is flowing more than ebbing.

4. Budget. No one’s getting out of budgeting and many business owners (including yours truly) are guilty of underplanning here. Many businesses fail in their first year due to cash flow and budgetary issues. Don’t let yours be one of them. Pouring over spreadsheets is no fun, but it’s a necessary part of building your structure.

5. Have professional boundaries. See my post on not committing energetic suicide for the nitty-gritty on this topic. It’s all about how you relate as a professional to the world and it’s a plan that every good businessperson must create.

6. Take time off. If you’re going to overplan anywhere, let it be here. Stay fresh, stay sharp, and schedule time off. One thing we can predict is stress in the business world. No matter what, staying on top of the game is a good thing, and a well-rested businessperson is more capable of being and staying on top. (Maybe the next time I take a vacation, I’ll heed my own advice here.)

Take a look at your structure. How much of it is your doing and how much of it created for you by someone or something else? How much non-essential planning time is being used and how much of operations time is actually in operating mode? These are all good questions to answer honestly.

If you’re looking to create a structure of your own to work within, you need help. Luckily, there are lots of smart people around to lend a hand. Some of them even have PhDs. Give me a call if content marketing fits into your successful business structure. We can build together.