The Essential Management Mindset for Small Business Owners

Is Your Brain Primed To Grow Your Business, Make More Money, and Get More Satisfaction From Your Company?

Hi, I’m Tara Gentile and I wrote this tiny book to help small business owners move beyond the endless hustle and experimentation of the startup phase. If you’re here because you’re tired of trying to keep up with the hot new thing, if you’re over throwing time and money away on guesses, and if you’re ready to act with more confidence, intention, and resolve, I wrote this for you.

After working with small business owners for over 7 years, I believe that a key ingredient in turning small business goals into reality is the management mindset. At some point, you have to stop guessing and start acting decisively to break through revenue ceilings, move past roadblocks, and overcome hurdles.

I call this skill self-leadership. By honing your self-leadership, you prime your brain to grow your business, make more money, and achieve more satisfaction from the company you’ve started.

The full text of this tiny book is below. If you’d rather read it on the go, all you need to do is enter your email address and I’ll send you a PDF version and an audio version absolutely free.

Photo by Trevor Mark Photography for VenturePop Conference

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Introduction: Or, How to Manage a Bookstore

My first post-college job was as a manager for the now-defunct Borders Books & Music. A big part of my job was wrangling a variable team of 40-60 overeducated, underemployed staff members to keep the store reasonably neat and tidy.

Our store was 25,000 square feet and contained about 140,000 unique titles. That meant that keeping the store “neat and tidy” translated to fighting a constantly uphill battle to alphabetize the shelves.

If you worked for me as a bookseller, I would assign you to tackle the Science Fiction section and you might start with Atwood and work your way towards Zahn. You’d scan the authors’ names on each shelf and pull out books that were out of order. Some books you could rearrange immediately. Others would go on a cart to be reshelved appropriately as you got to the right shelf.

Even for a relatively small section like Science Fiction, this process would take the better part of a day’s work. If you could take care of this task while the store was closed, you’d have a better chance of reaching completion. Unfortunately, we never had the payroll for that. So you would be alphabetizing a section of books while customers were browsing it and—you guessed it—putting books back where they didn’t belong.


When you reached the Z’s of Science Fiction, you’d look back and see the work you had just done completely undone. This bookstore fact-of-life made the job incredibly unfulfilling. For every customer you helped by putting the perfect new book in their hands, you had hours of work constantly being cancelled out by people browsing.

My job was to manage the inevitable daily disappointment our booksellers felt when they realized their 8 hours of tedious labor had already been undone. The antidote to the disappointment was balancing a vision for a tidy, easy-to-shop store with the realities of day-to-day work. I had to create and implement a strategy for staying on top of things while not creating expectations that just made everyone feel defeated. We chose to have an easy-to-shop store, not a perfectly alphabetized one.

If the challenge of avoiding the disappointment of work that is never finished sounds familiar, it’s not surprising. Entrepreneurship is a constant battle between your vision and the realities of showing up to work every day.

You show up day in and day out only to be bombarded with shiny objects, knowledge gaps, diminishing returns, or changes in the market. The space between your vision and your everyday actions can become a chasm.

There’s a misconception that following those shiny objects, filling those knowledge gaps, and optimizing those diminishing returns will somehow finally produce the vision you’ve dreamed of. They will not. Success isn’t something you stumble on. It’s not something that just happens one day when you least expect it.

Because of the very nature of operating a bookstore (I’m looking at you, customers who don’t put things back properly!), you don’t get a neat and tidy store by just showing up every day, putting your nose to the grindstone, and alphabetizing shelves. There needs to be a strategy for how you’ll tackle the challenge. There are decisions to be made about what sections take priority, what “good enough” looks like, and how much time should be spent doing what.

In my bookstore, I was the leader. I had to make those decisions. I had to pay attention to what counted. I had to devise a process.

In your business, you don’t have a leader. You are the leader.

You have to lead yourself to success. It’s deliberate. It’s strategic. It’s systematic.

Business owners who learn the habits of self-leadership and reverse engineer their plans are more focused, experience more fulfillment, and achieve their goals more often.

Over the course of this small book, I’ll introduce you to the discipline of self-leadership and entrepreneurs who are truly excelling at it. I’ll share my proven process for action planning with a strategic focus with you. And, I’ll show you how working backwards will change the way you approach your business as a whole and your daily work in detail.

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Filling Your Air Sandwich: The Problem of Management for Small Business Owners

Ham and cheese. Roast beef and cheddar. Tomato and mozzarella. Sandwiches should have filling.

Yet, that’s often not the case when it comes to businesses. Let me explain. Business owners most often have a hearty loaf of vision and hustle. They know what their dream is and they know how to rock out a to-do list on a daily basis. They’re willing to dream big and work hard.

But that’s not enough.

Nilofer Merchant calls this an Air Sandwich. In her book The New How, she writes:

“An Air Sandwich is, in effect, a strategy that has clear vision and future direction on the top layer, day-to-day action on the bottom, and virtually nothing in the middle — no meaty key decisions that connect the two layers, no rich chewy center filling to align the new direction with new actions within the company.”

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In your business, this likely manifests as feeling out of touch with exactly how your hustle translates into results. You feel a little (or a lot) fuzzy about what you should be focusing on and what really counts. You spend quite a bit of time seeing what “works” but what works doesn’t seem replicable, sustainable, or capable of building true momentum.

You learn more and more every day about what you could be doing in your business. Your to-do list grows every day with what you should be doing to grow your business. You put in the time and check things off the list. Yet, for each day you work, your vision doesn’t seem to get any closer.

Vision and hustle will get you into business but they won’t get you where you want to go. If you want to break out of the startup stage (where things feel disjointed, ill-defined, and often infuriating), you need to fill your sandwich.

Now in a big business, the Air Sandwich is filled by the decision-making that happens at the management level. Managers take direction from the vision of the executive level and the feedback from the people working to implement that vision to make key choices that determine an effective path forward.

In a small business, where the business owner often acts as executive, manager, and implementer, management looks different. That’s what I call self-leadership. Decision-making is still key but you have to find a way to detach yourself from both your vision and your everyday work long enough to make objective and creative choices. You also have to pay attention to what’s going on outside your business so that you have the best information for designing your plan. Finally, you need to be able to work backwards, determining your key actions from your vision and not the other way around.

Merchant goes on to write:

“Perhaps people fixate on execution (‘doing what’s required’) instead of finishing up strategy (‘choosing the direction’) because it’s easier to see progress during execution than during strategy formation and development.”

My clients often ask me what they need to do to create a website that converts more traffic into subscribers, or what they need to do to craft a Facebook ad strategy that works, or what they need to do to land coverage in a major magazine. They know these are things they could be doing. However, they haven’t determined how they’ll achieve their vision so they end up wasting time implementing things that just don’t matter.

You can’t determine what you need to do until you know how you want to achieve your vision. Yet, the “what” is so seductive. It tricks you into thinking you’re moving forward. Plus, it’s Google-able. We all love a problem where the solution is only a search result away.

You can’t google the “how.” It’s up to you. This is scary, unpredictable, and uncertain. If you don’t face it, though, you’ll be flitting from solution to solution for the rest of the lifespan of your business instead of moving forward toward your vision.

Self-leadership is about getting comfortable with the discomfort of answering that “how” question.


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Make Bold Choices: The Difference Between the Grind & Success

Strategy—and answering the “how” question—is really about making choices. Your business strategy will have you say “yes” to a few things and “no” to everything else.

While others can give you their perspective, you as the small business owner ultimately have to make these choices for yourself.

Take Nathan Barry for instance. Nathan was a software designer and information marketer. He created several successful programs, including The App Design Handbook, and wrote a book called Authority. He was very successful with this business, yet he continually ran into limitations with his email marketing provider. Those limitations cost him money and time.

He had an idea: he’d build his own email marketing provider. He founded ConvertKit on the premise that email marketing should be easy-to-do and that it should allow you to deliver what subscribers actually want from you, whether that’s content or a pitch for a product.

Nathan announced this new venture to his list and generated about $2500 per month in recurring revenue with his first wave of new accounts. Those sales were nothing to sneeze at but they also weren’t anything to retire on. He continued to run this business as a side project and put his attention on the information business where he was generating considerably more revenue.

Unfortunately, “recurring” revenue doesn’t always recur. Thanks to customer churn, the amount Nathan was making started going down. Yet, he persisted.

Nathan shared his progress with a friend at a conference. That friend—a successful startup veteran—told him to shut it down. If it was going to succeed, it would have succeeded by now, he said.

The friend went on: or, he could decide that making it succeed was what was most important and quit running it like a side project. Nathan could either give it the time, energy, and investment it deserved, or he could quit.

So Nathan did what most of us would do and put off making a decision for another 6 months. He prioritized hustle and status quo execution over making a tough decision.


Over that time, churn continued to wreak havoc on his monthly sales. Finally, enough was enough. He made a bold choice to move forward with ConvertKit.

The decision was the hard part. What came next was fairly straightforward. He put his information business on autopilot first. Then, he took a chunk of his savings and hired a full-time developer. Finally, he embarked on an direct sales campaign to reinvigorate his revenue growth.

A short time later, ConvertKit is on a $1+ million run rate. Top bloggers and content marketers (like this author) use it for their email marketing efforts. His system has integrations with most of the top marketing tools available.

One bold choice changed the course of Nathan’s business and his life. He connected his vision and hustle with a real strategy and disciplined self-leadership.

Nathan’s bold choice was about realizing his overall vision. But bold choices often happen on a much more frequent basis. Take Danielle LaPorte. Danielle is a writer and spiritual evolutionary. She’s published 3 digital programs and 2 books, and she’s working on her third.

She’s taken different paths to publication for each one. When I asked her how she decides what path she’ll pursue when she’s working on something new, she focused on her constant top priority: “I as a human being, woman, person, need to be self-expressing.”

As she listed each of her projects and how she published them, it was clear that the way she wanted to self-express was different in each scenario. To choose, she determined her “how” and chose the “what” accordingly. For the original digital program version of The Fire Starter Sessions, her self-expression was fast and furious. She wanted to create something beautiful as quickly as possible. For her forthcoming book, The Manifesto of Encouragement, Danielle wanted her self-expression to be realized as powerfully as possible in the world and so a traditional publishing deal was the way to go even if it meant a few trade-offs on other things.

Decision-making is what self-leadership and strategy are all about. If there are no decisions, there is no strategy. If there’s no strategic decision-making, there is no success.

Others self-leadership can seem like magic, like they were in the right place at the right time or that they had the perfect idea that no one else had had. But it’s not like that. Their self-leadership is intentional and, first and foremost, they make bold choices as they exercise it.

As you’ve already seen with the previous examples, the choices aren’t about what’s right or wrong. There are many ways to achieve the same goal. However, that doesn’t mean that you can try all those different ways on for size and expect to achieve what you want. If you want real traction and momentum, you have to choose.

Take a look at Toms. Toms has sneakers, sandals, platform wedges, and all other manner of shoes now. They also have a whole marketplace of goods by other companies. But in the beginning, Toms sold only one style of shoe. They made a decision to go to market with one style and focus their marketing on the One for One campaign.

Toms decided to be a give-back-first company instead of a shoe company. If they wanted to be a shoe business, they would have gone to market with more than one kind of shoe.

Toms decision wasn’t a question of right or wrong, good or bad. It was a question of values, preference, skill, strengths, and effectiveness. Toms decision was about how they would meet their end goals–not just sell shoes.

When you’re making bold choices about the direction you’ll take in your business (the how), prioritize your own values, preferences, skills, strengths, and effectiveness too. That way you’re never at risk of just trying to duplicate someone else’s direction (it won’t work).

Now, consider Amazon. Amazon has made the decision to be a logistics company, not a bookseller. They may have started by selling books but Jeff Bezos put the most investment into distribution logistics from the get go. Now, they can sell almost anything and ship it to you in 2 days.

Even the development of the Kindle fits this strategic decision. Want a book? You can start reading it immediately. That’s logistics.

If Amazon wanted to be a bookselling company instead of a logistics company, they would have invested more initially in connecting readers or helping you find your next book.

Look at your own field. What do some people say “yes” to when you’re firmly a no? What do you see as the conventional way to do things and how would you prefer to do it differently? How have the decisions leaders in your field have made affect the way their businesses are perceived?

What can you decide to focus on that puts your business in a category of one like Amazon or Toms? How will you decide the next best step like Nathan Barry or Danielle LaPorte?

Making a decision to go a different direction, to make a choice other than the default, is a strategic decision. It puts your business in a category of one. It allows you to manage yourself and your business with clear parameters. When based on your strengths and unique effectiveness, it makes your business more compelling. Making a strong and interconnected set of choices is the first step toward success.

Other strategic decisions are who you’re going to serve, how you’re going to connect with them, what price point you want to charge, how you’re going to package and deliver your offer, or what emotions you want to evoke when people use your product.

The more intentional you are with the decisions you make, the stronger your strategy and the deeper the connection between your vision and your everyday actions.

Now, not every strategy works—but to even have a chance at success, your strategy needs to be based on focused, intentional decision-making. Every decision you make is an opportunity to put your product or business in the best possible position for success.

If you resist making decisions, you resist success. It’s as simple as that.


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Work Backwards: The Fastest Route to Any Destination

Imagine you’re starting a vacation road trip to a new destination. You have a vague idea that you’ll need to hop on the interstate and go north but, beyond that, you’re not sure where you’re headed.

What’s the first thing you do? You program the GPS.

Side note: what did we do before GPS?


You tap the Google Maps button on your phone and input the destination: Ithaca, New York. It thinks for a split second and suggests 3 routes. You choose the one that suits your driving style and it lists the step-by-step directions.

This makes sense to us when it comes to driving. Unfortunately, it’s not the way we tend to operate our businesses. Instead, we tend to either give our strategic GPS an incredibly vague destination (i.e. New York instead of Ithaca) or we try to find the “right” way to get to the interstate and ignore the following 5 steps.

The vague destination means we don’t know whether we’re on track or not (Buffalo is the same as Ithaca, right?) Or, we’re not looking for our exit because we were just so hell bent on getting to the interstate in the first place. Sound familiar?

Businesses are built by working backwards. It’s more efficient, more effective, and more precise than trying to take each step as it comes. With your destination in mind, you’re more likely to make good choices about the route you take to get there and, when you inevitably get off track, you’re more likely to make your way back to the road you want to be on.

Your trip takes less time, you argue less with your spouse about which way to turn, and your kids don’t have to constantly ask, “Are we there yet?”

Abby Covert writes in her book, How to Make Sense of Any Mess, “When we jump into a task without thinking about what we’re trying to accomplish, we can end up with solutions to the wrong problem. We can waste energy that would be better spent determining which direction to take.” Business owners don’t have time to waste. If starting with what you’re trying to accomplish will save you time and energy, it’s definitely the right way to go.

Take Laura Roeder, founder of social media scheduling software Edgar. Laura discovered a problem that business owners had while she was building her social media marketing agency and training company. But she wanted to move away from both the agency model and the information products market.

What she really wanted was a software business–a software-as-a-service business, to be specific. Many of these types of businesses are built by venture-funded startups. Laura was really attracted to that model, just as Nathan was earlier, but Laura also knew that she was ready to start a family.

Well, starting a startup and starting a family do not go together. In fact, venture capitalists do not want to give you money if you then want to turn around and take maternity leave. So Laura took these 2 goals, “I want to start a software company” and “I want to start a family” and worked backwards from there. The intersection of those two goals became her GPS point.

As she figured out the route between where she was and her new destination, a bold choice became clear: to not accept venture capital for this company. This had a lot of upsides: she maintains control, she can start a family, and she doesn’t have to answer to a board.

It also had a downside: “…to be honest, I was tempted to get in on the startup ‘game.’ Without fundraising, I would continue to be an outsider. No press in TechCrunch, no gallivanting around San Francisco, no speculation as to whether my company would be the next unicorn,” she wrote on Medium.

And this is really why working backwards is so important. When you’re focused on moving toward your destination, both tines of the fork in the road look equally viable. They both seem like they could lead you towards your destination. But, it’s not true.

When you work backwards, you see that the most direct route—and sometimes the only route—between where you are and where you really want to be goes one direction and not the other. Without Laura knowing that starting a family was an important next goal for her, she might have been wooed by the promise of taking venture capital.

Now her business is generating 7-figure revenue and it’s afforded both her and her husband, the CTO of the company, the ability to take maternity and paternity leave and work part-time when they returned.

Laura’s example is a good one for how working backwards allows you to make high-level decisions with more clarity and ease. But it doesn’t stop there. Working backwards can help you plan your daily activities and operations, as well.

Theresa Reed is The Tarot Lady. She’s been working full-time in her tarot and astrology business for 25 years. She has her business systems down pat. One of those systems is her backwards annual planning or, as she calls it, her “very big planning.”

It starts by choosing the number (revenue goal) that she wants to work towards. She says, “I like to know what my number is because that gives me great clarity on how much work I need to do, how I need to price things, and how I need to make things work to achieve those financial goals.” From there, she breaks the goal for the year down into monthly goals.

The monthly goals turn into how many in-person readings, how many email readings, and how many other projects she needs to do. Those sales goals turn into a marketing plan. She also asks herself, “Do I need to raise my rates this year in order to achieve this? Am I working too hard? Do I need to pull back a little bit?”

Being a tarot reader and astrologist, Theresa also consults metaphysical sources. Once she’s worked backwards into monthly revenue goals, sales goals, and a marketing plan, she has a framework for applying her skill and insight through astrology to the actions she’ll take throughout the year.

Doing it that way, she says, “I can ensure that I can reach my goals financially and, also, do it in a way that’s going to leave plenty of breathing room for mistakes or twists or turns or anything that may come up or even changing my mind.”

That’s the other thing working backwards does: it gives you wiggle room. In the same way Google Maps can reroute you when you’ve taken a wrong turn, you’ll have a much better shot at getting back on course when you’ve created your plan backwards from your goal.

When you know what you want and where you want to end up, it’s a lot easier to focus on the work that’s going to get you there.


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Pay Attention: The Only Way to Get Ahead

If you’re focused exclusively on your vision and to-do list, you’re missing a treasure trove of information that can help you choose the direction you want to go. That’s why the final step in building your self-leadership discipline is to pay attention.

It’s become rather fashionable for overworked, overstimulated, over-media-inundated business owners to disconnect from the world. They don’t read the news. They don’t read magazines. They don’t watch TV. They don’t keep up with any blogs or social networks.

This is a mistake. It’s a big mistake.

Now, that’s not to say that we should let our overwhelming and noisy world rule our lives. You can’t be connected to or pay attention to everything that’s being hurled your way. But checking out isn’t the answer either.

Self-leaders pay attention. So the question becomes “What do you pay attention to? How do you pay attention?”

The answer to this question—especially for entrepreneurs and business owners—is to pay attention to the things that are influencing your industry and influencing your customers. You can’t afford not to. Paying attention is what pays the bills, keeps you ahead of the curve, and allows you to foresee problems before they happen.

Paying attention also helps you see opportunities.

To see this in action, look no further than Sue B. Zimmerman. She’s @TheInstagramExpert now but she wasn’t always. No, Sue B. Zimmerman used to have a boxer shorts company. Remember in the 90s when we were all wearing funky boxer shorts for no good reason? She’s partially responsible.

Here’s the story from Sue:

“I opened my first business called Color Me, and I was hand painting so many things so quickly, and they were selling really well. But what was really flying off the shelves were hand-painted boxer shorts, and this was before people were wearing them as outerwear. So I was in. I was feeling the pulse of this trend just transforming and exploding. So I put all my energy into the boxer shorts, because that’s what people really wanted.”

Even with her first business, Sue paid attention. She could have grown Color Me doing what she started doing. But she noticed there was something working even better and sensed that could be an even more promising direction for her to go. And so, Boxer Rebellion was born.

At just 22 years old, Sue had taken her first business, rebranded it, and went to the major trade shows to introduce retailers to the boxer shorts trend. She wrote over $1 million in orders in her first year in business.

But Sue never stopped paying attention. Sometime after she sold her boxer shorts company, she started a boutique in Cape Cod. She employed a number of younger women—her daughters and their friends—and she noticed that they regularly had their phones out.

Okay, nothing unusual there.

But as these young women stared at their phones, they were just scrolling. They weren’t tapping and texting. When she asked them what they were doing, they reluctantly told her about Instagram.

Sue researched how other brands were experimenting with Instagram and decided to give it a shot. Sooner than later, she had customers coming into the store, showing her their phones, and asking for items right from her Instagram feed. That’s when they ramped up their efforts and Sue asked her staff to start posting to Instagram about what was in the store too.

Her sales increased 40% and that’s when she decided to start teaching this to the world.giphy (1)

Paying attention to trends and market forces has allowed Sue to build successful business after successful business. Her ability to spot what’s next and optimize for it allows her to stay on top.

Often what you need to pay attention to isn’t an outside force like Instagram but instead a personal struggle. About 8 years ago, my friend Amanda Steinberg noticed that despite a big salary from her web design agency she wasn’t saving much. She had a story about what her relationship was with money: she was a good earner, not a good saver.

So she started looking for financial information. She wanted to learn about saving, investing, and being a good steward of the money she earned. As she poured through resources like Yahoo! Money, Money Magazine, and Market Watch, she noticed that 90% of the people reading these resources were men. That piqued her interest.

She knew from her own experience that women were interested in financial information. But, there was something stopping them from accessing what already existed. She knew there was a huge opportunity to take good information, package it in a way that appealed to women, and build an education company out of the results.

The main difference that she saw between the information and education that existed at the time and what women were really looking for was a respect for the big picture. She said, “We’re more interested in the comprehensive life picture, how money fits into that, and how to think about money. … The way financial advice had been delivered online before [my company] came along just didn’t resonate with how women thought about money, which is much more in the context of their life, not about what kind of stocks do you buy and sell.”

So her company, DailyWorth, was born. She’s grown her audience to over 1 million subscribers and won the respect of the good ol’ boys’ club of finance. She’s signed major banks to big advertising contracts. And, most importantly, she’s helped women change the way they see themselves, their money, and their potential.

Amanda hasn’t stopped there. Because she kept paying attention, Amanda realized there was an opportunity to serve women with a new kind of financial management system. It’s called a robo-advisor, an emerging type of software that helps manage a financial portfolio depending on your priorities, values, and goals—without involving a human advisor.

Amanda and her co-founder, financial advisor Michelle Smith, created WorthFM. Sticking with the “big picture” idea, they’ve divided their services into three areas: Savings (short-term money), Investing (mid-term money), and Retirement (long-term money). They’ve also paired the service with a comprehensive survey about users’ goals and money style. They’ve also developed a free assessment people can use to identify their money style, called MoneyType™ even if they’re not ready for WorthFM.

Amanda was able to see that this opportunity was the right one for her and her business because she knew where she wanted to end up. She knew that her chief goal was empowering women to become wealthy, affluent stewards of their money. Working backwards from there, this problem she detected for her subscribers and this trend in the market became the best next step for her.

When you’re working backwards and making bold choices about what’s next, you have the perfect filter for paying attention to what matters and discarding the rest, just like Amanda. If you’re not paying attention, you will miss opportunities to lead your business and yourself in the right direction. Be ruthless with the information you consume and the stimulation you open yourself up to—but never stop paying attention.


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Declare Your Chief Initiative: Create an Integrated Plan to Manage Your Business

Now, I know it’s not enough to just say “make bold choices, pay attention, and work backwards.” If it was that simple, you’d be doing it already. With some structure, this method turns into a powerful way to manage your business.

I call that structure your Chief Initiative. Declaring your Chief Initiative and creating a plan to bring it to fruition will create the structure, context, and benchmarks you need to make better choices, pay attention to the right things, and work backwards most effectively. Your Chief Initiative can take a smattering of conflicting priorities, a swarm of good ideas, and an overdose of your mission and turn it into a system to accomplish what you really want.

By working your Chief Initiative, you can avoid the problems associated with a lack of self-leadership: not knowing what to prioritize at any given time, not knowing how to execute the new knowledge as you learn it, and not knowing what your next moves are.

We’ll begin by asking the $64,000 question: “What is the one thing you want to have accomplished or created [3, 6, or 12] months from now?”

If your business is less mature, choose 3 months. You need more time to pivot because you’re still experimenting, and so it’s harder to look further into the future. If your business is more established, you can choose a 6-month goal. If you have a more mature business and you have a lot of experimentation under your belt, choose a 12-month goal.

Challenge yourself to look further into the future than you currently feel comfortable. Try and see yourself there. Then decide on the 1 thing you want to have accomplished in that time frame.

This accomplishment has to be that thing that can get you out of bed every day. It has to be that thing that helps you get past those projects that are frustrating, that work you don’t love to do. Because let’s face it, we all have to do that work sometimes. Even if you’ve got a team to delegate to, there’s going to be something you run into that you don’t love. I want you to choose that 1 accomplishment that’s going to motivate you through those tough times.

Choosing one thing is important because it gives you a focal point, those GPS coordinates you need to get where you want to go. Once you know what that is, you need to ask yourself “How will I know when I’ve achieved it?”

You have to define success to be able to achieve it. This is where we so often go wrong—not only as business owners, but just as adults. In school, we had certain expectations and benchmarks. You complete your homework, or you don’t. You take the test, or you don’t. You finish the school year, or you don’t. You do what you’re supposed to do and you advance to the next grade. Everything is clear cut, and the consequences of not doing what you’re supposed to be doing are fairly severe.

But in work or our businesses, your actions are rarely tied to clear consequences or benchmarks. You show up, do work that’s assigned to you, and go home. Most of the time, you don’t know how that work is impacting the bottom line or progress towards bigger goals.

Discontentment grows. You lose faith and focus. Your growth stagnates. This is a serious problem.

In all the reader and customer research we’ve done, this problem has presented itself. You’ve told us that you don’t know how the work you’re doing today will get you where you want to go. You’ve told us that, because you lack focus on a particular goal, it makes it difficult for you to decide what’s next. You’ve told us that there are so many things demanding your attention that you don’t know how to prioritize. You’ve told us that you understand a lot of things in theory but that you have trouble when it comes to applying things because there’s just so much to do.

Yes, that’s a recipe for frustration. And, it’s also a recipe for the stagnation that leads to throwing in the towel. It’s exactly what contributes to so many goals going unachieved and so many business ideas abandoned.

The key to avoiding this problem is creating benchmarks that allow you to say, “I’m done.”

It sounds simple and it is. But you don’t do it.

You say “I want to become influential in my field” instead of “I’m going to book 5 speaking gigs at major industry conferences.” You say “I’m building my signature program” instead of “I will sell 150 seats in the program I create by September 30.” It’s the difference between telling yourself you’re going to train to run some far-off race and actually counting the hurdles you clear, one after another.

The mindset shift you need to make here is that it’s not about doing the work; it’s about overcoming the next obstacle. “Doing the work” isn’t what a leader does. Leaders solve problems, overcome impediments, and break through barriers. To lead yourself backwards, you need a clear hurdle to jump over.

What you see in front of you right now is work, not hurdles. If you want to up your level of satisfaction and intensify your focus, transform your work into hurdles.

The moment you change your goal into an obstacle to overcome, you will accomplish more, feel a greater sense of satisfaction, and make measurable progress towards your greater vision. You’re a problem-solver and a barrier breaker. This is in your wheelhouse.

Revisit your answer to the question: “What is the 1 thing you want to have created or accomplished in [3, 6, or 12] months’ time?” Is it a particular magazine that you want to be in? Is it a particular speaking gig that you want to get booked? Is it a particular income threshold? Is it a particular product that you want to have created, and by what deadline? Make it quantifiable, time-bound, or specific. Turn the work into an obstacle.

Now, you have your destination—your Chief Initiative—finalized: a big, hairy, specific goal. It’s time to figure out the route you’re going to take to get there.

The next step is to name at least 3 projects that you need to complete to make your Chief Initiative a reality. Here’s an example: Let’s say you want to get a book deal in the next 12 months. What are some of the projects that you would need to accomplish that? You’d need to get an agent. You’d need to complete a book proposal. You’d need to build your email list to at least, say, 7,000 people so that publishers take you seriously. Those are 3 of the projects that will help ensure you accomplish your goal. Each of those projects can be broken down into more and more steps.

Declare Your Chief Initiative

Now that you have at least 3 projects that lead to your Chief Initiative, each of these projects needs a specific benchmark or goal, just like your Chief Initiative. In other words, how will you know when you accomplished each project? Again, assign a deadline or metric so you’ll know when you’ve overcome the obstacle.

To complete each project, you’ll need to execute both deliberate action and consistent action. The deliberate actions are things that you can put on a to-do list. Once you cross them off the list, you don’t need to revisit them. Consistent actions are things that you have to keep doing over and over again. You can check it off your list, but it’s just going back on there the next day or next week again.

The things you’re taking deliberate action on are Action Steps. The things you’re taking consistent action on are Action Standards. Each project will have both Action Steps and Action Standards associated with it. So your backwards leadership plan will need to incorporate both.

Action Steps are things like “Write the sales page by Friday,” “Choose an agent by June 1st,” “Create a welcome gift by April 3rd,” or “Launch a podcast by October 30th.” Notice how they each have deadlines. They could also be quantifiable: “Write 1,000 words today.” Just like with your Chief Initiative and your Projects, you have a clear indicator that each Action Step is complete. Words like “begin, start, work on, or continue” should never be part of your Action Steps because they cannot be definitively completed.

Action Standards look something like this: “Pitch 5 media outlets per week,” “Conduct 3 sales calls per week,” “Write 5,000 words per week,” or “Interview 3 customers per month.” You can break it down by days, by weeks, by months, by quarters, whatever frequency you need to get that consistent action happening. If you don’t know the precise amount of an action that will get you to your goal, take a guess. Start somewhere and adjust as you measure your progress.

Declare Your Chief Initiative

So this is what we have so far: your Chief Initiative is your focal point, then you have projects to organize your planning, and then each project is broken down into Action Steps and Action Standards so that you can measure progress on a small scale. But this doesn’t represent the reality of running a business. It doesn’t take into account the emergencies, the new opportunities, the failures, and the unexpected situations that inevitably occur during the life of your plan.

It also doesn’t take into account the fact that big, hairy goals are never accomplished start to finish. You may need to start Project 3 while you’re halfway into Project 1 to stay on track. You may need to start Project 2 and then delay the completion of that project until you complete Project 3. That’s just how running a business goes. There is a lot that needs to get done and very little of what needs to be done can be easily ordered or accomplished in line. Projects overlap, actions items move up and down the priority list. It’s a lot of different things coming together to make one main goal a reality.

This is a big reason action plans fail so often in businesses. Your action plans fail because they assume your goals require linear action–execution. You try to create a set of steps to follow instead of a strategic map that incorporates all areas of your business.

Once you’ve passed the startup stage of your business, all of your execution has to be integrated action–management–instead of linear action.

Linear action is “first I do this, then I do that, then I’ll do the next thing.” Integrated action means knowing that when you act on one thing, it affects many other parts of your business. One simple action can create a chain reaction of necessary follow-up actions.

To get the most out of any plan, you need to account for how you’ll manage those chain reactions. Some, you’ll act on immediately. Those are the things that best support your strategy and help you create the most amount of leverage. Others, you’ll intentionally put on the back burner. You can’t do everything right away.

You also need to know your overall strategy for each area of your business so that once you realize a chain reaction is occurring in that area, you can act with intention in line with your strategy and Chief Initiative.

Your projects form the backbone of this strategy. Each one of your projects warrants its own linear action plan. But again, without integrating that into the overall plan, those action plans are worthless.

If you try to reduce your action plans to purely linear action, you’ll always (and I mean, always) come up short. A formula—even one of your own creation—is just never good enough. One step in that formula will always lead to another chain reaction of steps.

This is also why it feels like you’re regularly biting off more than you can chew. Once you get started on a good plan, it quickly spirals out of control because you realize just how much more there is to do.

One way I’ve found to effectively combat this chain reaction problem is to premortem my plans. A premortem is essentially a way to reverse engineer your problem-solving and incorporate the results into your action plan to begin with. When you do a premortem, pretend your plan has utterly failed—the patient is dead on the table—then list any and all reasonable factors that could have contributed to its failure.


I want you to imagine that you’re on the verge of accomplishing your Chief Initiative. Think about all the work that you’ve done to that point, all the emails that you’ve spent, all the time that you’ve tracked, all the team members you’ve hired, all the projects that have been managed. And now fast forward a day, or 2, or 3, and imagine falling short of that goal. Imagine the seats not being filled, the dollars not coming in, the publishers saying no, the call for the speaking gig never coming.

Clearly, motivating visualizations are not my calling.

Why did that happen? What caused this breakdown? What came between you, your company, and victory?

The answers to that question of “Why did this happen?” are things you may need to add to your plan. They might be additional Projects, Action Steps, or Action Standards. They may be adjustments to your plan, bigger goals, or more ambitious action. If you hate backtracking on your plans, if you hate how they never quite work out the way they’re supposed to, a premortem will all but fix that. Now, you’ll have a plan that incorporates unexpected situations and contingencies.

Now that you’ve created multiple linear action plans (each Project) and incorporated countermeasures for potential pitfalls thanks to your premortem, it’s time to integrate your plan and put it on a calendar. This becomes your roadmap, your integrated action plan.

Declare Your Chief Initiative

Until we have finally perfected the time machine, you’ll still need to work forwards through your plan. But at least that plan was based on leading yourself backwards.

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Conclusion: You Are The Leader Your Business Needs

It can be tempting to think that, when your business isn’t quite working or when the time you invest in it isn’t producing equal results, there’s something wrong with you. Maybe you think you’re not cut out for this entrepreneurial stuff or that you’re an artist, thinker, writer, or coach instead of a businessperson.

It often seems easier to blame the missteps on yourself than the way you’re tackling the job to begin with.

You want to be more productive, more knowledgeable, more influential, more likable. But it’s likely that the reason those things are not occurring is because the core management system of your business has been ignored.

You’re operating in a dizzying dance between vision and hustle because you haven’t taken the time to make bold choices, pay attention to the right things, or work backwards to know what’s really important. You don’t have a framework for judging what’s working, what could help, or what to prioritize.

The problem isn’t with you–but it might be in how you’re trying to fix the problem. You can’t spend more time on the grand vision for your business and hope it will come true. You also can’t hustle your way to success. You need a plan, a road map, and clear direction—and I propose that that direction is backwards.

giphy (2)Leading yourself—and your business—backwards ensures that you’re focused on where you want to be, the action that will contribute the most to that result, and the metrics of success that actually matter. That’s management. It’s a crucial component of taking your business past the startup stage and guiding it into the growth and leverage stages.

Management–and the strategic decision-making that comes with it–is the difference between seeing more hustle as the only solution to your woes as a business owner and having systems in place that get results with less work.

What safeguards do you need to put in place to ensure you make bold decisions instead of hedge or waffle on tough choices?

When can you set aside time to determine your end-goal and make sure the plan you’re operating under can actually achieve it?

How can you create a system for paying attention to the right things so that you’re ahead of changes and not blindsided by them?

These are the kinds of questions that smart entrepreneurs wrestle with so that they’re not just running their businesses, they’re leading them.

My challenge to you is to start (or continue) wrestling with these questions too. Take a break from the daily grind and get serious about leading yourself.

Your next step is to have a meeting with yourself about the answers to these very questions. Allow yourself to get uncomfortable because it’s a natural part of the process. Question everything. Assume nothing. Create your backwards leadership plan and follow it.

You are the leader your business needs.

Enter your email address to download a PDF version of this book to read anytime. You’ll also receive an audio version for listening on the go.