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Book Chapter - Creating Your Winning Strategies (Issue #375)

Book Chapter - Creating Your Winning Strategies (Issue #375)

How will you compete to win?
Map and compass
Photo by Denise Jans on Unsplash

A flawlessly executed plan will fail if the overarching strategy is flawed.

Let me use a hypothetical situation with a cafe named “Beanville” as an example. Beanville’s strategy to win in a competitive marketplace was to offer the lowest price option to customers. So, Beanville created a plan to acquire, create, and sell the lowest-priced coffee products in town. That plan included all the details required to keep costs down:

  • Low-cost commercial real estate

  • Sourcing the cheapest coffee beans

  • Aggressively negotiating with suppliers

  • Low production costs

  • Minimum wage employees

  • Low-cost packaging

  • Pricing and sales strategies

Unfortunately, Beanville’s core strategy was flawed. They discovered that customers in town weren’t so cost-conscious that they were willing to sacrifice the quality of their coffee drinks to save a little money. So, Beanville lost to its competitors, who delivered a better product. Even though they flawlessly executed the plans to support their lowest-price strategy, they still failed. This is why choosing the right strategy matters so much and why it must happen before you go into planning mode.

So, let’s take the time to create a winning strategy that will help you achieve your goals. Developing the right strategy must come before making the appropriate plans to support it.

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Strategy vs. Plan

People often confuse creating a strategy with making a plan. As Chris Kolenda succinctly points out, here are three critical differences between strategies and plans:

  1. A strategy faces outward, while a plan faces inward.

  2. A strategy orients on factors you don’t control, while a plan focuses on what you do control.

  3. A strategy measures success, while a plan measures performance.

However, It’s easy to slip right past strategic thinking and into planning mode because the steps feel tangible and clear. “We’ll do x, then y, and then finish with z.” Unfortunately, intense and detailed planning does not ensure success.

A perfect plan won’t save you if the underlying strategy is the wrong choice. Looking back to your vision and mission in chapter 4, think of your vision as an inspirational flag planted on the horizon. That point — shrouded in misty clouds —is your ideal destination. That’s where you want to be.

Your mission is what you will do to make that vision become a reality. You know you need to move from where you are standing to that point on the horizon. In chapter 7, you identified the goals you need to achieve to get there. You can think of those as waypoints along the path you choose. But, you also know the journey will be complex, bumpy, and full of obstacles that will try to stop you.

That’s where your strategy comes into play. Your strategy is how you hypothesize you can navigate that mysterious landscape to follow your mission, achieve your goals, and reach that vision. Let’s play around with this metaphor for a second to make the distinctions clear.

If your vision is to reach a specific mountain peak in the far distance, you could choose one of the following strategies to get there and overcome the obstacles in your path:

  • Float over the landscape in a hot air balloon and land on the mountain.

  • Fly in a small plane and parachute down to the mountain.

  • Take a boat down the river that leads to the mountain's base and climb to the peak.

  • Ride a horse through the countryside to reach and ascend the mountain.

  • Hike the entire way to the mountain on foot and climb to the peak.

Those are all valid strategies, but each one has pros and cons. Eventually, you will choose the strategy you are best able to employ, hope will take you past all obstacles, and has the greatest chance of success.

Once you have selected a strategy, only then would you start creating a plan to set that strategy in motion. For example:

  • Acquire funds.

  • Purchase equipment and supplies.

  • Map the best route and account for travel speed, time, waypoints, resupplying, etc.

  • Hire experts and guides.

  • Acquire the necessary training, skills, and knowledge.

  • Your strategy can’t predict the weather, but your plan certainly can prepare for the worst.

  • Create a Plan B, so you’re prepared if Plan A fails.

Too silly? Ok, let me share a personal example instead.

I’ve had a long-term vision of living in a cozy cabin in the mountains surrounded by a forest for most of my life. I spent decades with this image in my mind as I made my way through childhood in Nebraska, graduate school in Texas, and a tech career in Silicon Valley. I knew where I eventually wanted to be and what I wanted my life to be like, but it seemed far, far away in the future.

However, a health scare woke me up several years ago, and I decided I shouldn’t put my dreams off forever. So, I made it my mission to make that vision come true. We had to find a way to leave Silicon Valley and move closer to the mountains where we always enjoyed spending time and wanted to make our new reality.

I’m not the kind of person willing to shoot from the hip and hope things work out. I have a family to support. So, I began exploring various strategies that could make a move possible. One strategy was to reduce our cost of living to give us more flexibility in our income. Moving out of the Bay Area and into a rural area was part of that strategy.

Yet, I still needed to make a living somehow. I had spent decades working in tech, which is why we had moved to Silicon Valley in the first place. But, how could I maintain my career in tech if we moved to a rural area far away from the heart of it all? Note: This all occurred several years ago before the pandemic and the changes it enabled for jobs like mine.

I came up with a few possible strategies for making a living:

  1. Stay in my current career and find a tech job in a city within commute distance from our new country home.

  2. Leave my career and find a non-tech 9-5 job in our tiny town.

  3. Find a tech job with a company that would be ok with me mainly working remotely, but traveling to be in the home office every month.

  4. Found another tech startup and locate partners and employees who would also be comfortable working remotely.

  5. Leave my tech career and design a new business that fully supported my new lifestyle and enabled me to work remotely with customers and clients.

Long story short, I evaluated all of the strategies, what they would require, the fit with my desired lifestyle, and their likelihood of success. For one reason or another, the first four strategies didn’t seem to have the full potential and flexibility that the last strategy did. So, I finally went into planning mode to execute that strategy, set it in motion, and I’m happy to say that it’s been working well for the past few years.

Strategy must come first. And you must have enough research, innovative thinking, and cleverness to select a winning strategy. Then, and only then, can you plan to execute that strategy.

We’ll go into the details of the plan to build the “Invincible You” in a later chapter. Now, we’ll focus on ensuring you are creating a strategy — or strategies — that will help you successfully navigate the competitive landscape of your professional and personal life. These are the strategies that will help you achieve your most audacious goals.

First, I’d like to share a meta-level strategy that will fundamentally shift how you think about your career and work.

The Business of You

As you may have noticed, you will be creating strategies within strategies. A high-level strategy to win and achieve your goals will often have numerous lower-level strategies to accomplish various sub-goals (identified in chapter 7) and overcome obstacles.

Treating your career like a business is one of those meta-level strategies that sits above the specific strategy you will soon create to achieve your particular vision. But, thinking like a business doesn’t come naturally for many people. If you’ve been an employee your entire career and don’t plan on changing that, why would you bother to think like an entrepreneur running a business?

However, that’s precisely how you should be thinking about your career. It is very much like a business, with income streams, expenses, and products and services (i.e., you and the work you do) that you “sell to customers” (i.e., your employers).

This fundamental shift in my thinking changed how I viewed my career forever. I understood that the strategies that helped businesses succeed in a competitive marketplace could also be applied to my professional life. Branding, positioning, pricing, marketing, sales, etc., should all be a part of a successful career.

The Product of You

Seeing yourself as a “product” that you “sell” to customers is another meta-level strategy that elevates you above the emotional turmoil of job searches, competing for promotions, and getting ahead at work. It’s also the foundation of building a solopreneurial business based on who you are and what you do.

One of the fastest ways to define the product of you is to transform your current job description into a product description. How do you help your “customer” (i.e., your employer) succeed? What problems do you solve?

Break everything down into the fundamental building blocks of what you do. Don’t forget to capture your work that goes far beyond your simple job description. You’ll discover that the product of you is more complex and valuable than you think.

One surprising and exciting discovery is that these “building blocks” can be assembled in any number of ways to create variations of the product of you. In my long professional life, I’ve learned that intelligent, talented people can learn almost anything, do almost anything, and succeed at nearly anything.

We are more flexible and malleable than we think. Once you realize this, a world of possibilities unfolds before you. You start to envision radically different strategies that leverage different facets of the product of you to achieve your goals and reach your vision.

Then you just need to determine which strategy will best support the life you want and decide how you want to build, package, promote, and sell it (e.g., employment vs. entrepreneurship). We’ll get into those details in a later chapter.

A few more strategies

I want to share a few more strategies that can help you overcome the competition before focusing on your specific strategy to win.

Coming in the side door

The masses are following the rules. The masses are a little bit lazy. Sorry, but it’s true. The masses aren’t that good at what they do. Again, I’m sorry, but that’s the law of averages (I.e., the normal distribution of the population). Only a few people stand out on the far ends of the distribution.

If you want to stand out competitively — if you want to win — you can’t do what everyone else is doing. Be creative and dare to be different. Ignore that massive line of people queued up behind the velvet rope facing a giant bouncer who won’t let them into the club (i.e., your dream job with your dream employer).

“Different is better than better.”
— Sally Hogshead

Slip right past the velvet rope, walk past the bouncer, and down the dark alley to find that hidden door no one else knows about. Some rules are meant to be broken.

Leveraging your network

My first few jobs in tech happened because I knew someone who knew someone inside “the club.” I was able to leverage the power of my network. I doubt I would have landed those roles if I had followed the rules and waited at the end of the long line.

Instead, my graduate advisor called his old student at IBM. I was sitting in his office, and he said, “Hey, do you want to do an internship with a software company?” He picked up the phone, called him, and before I knew it, I was moving to San Jose to work for IBM.

A year later, a fellow graduate student introduced me to someone at Apple. That networking connection opened the door to a summer internship. That internship went so well that my manager at Apple reached out later and asked me if I wanted to stay on as an employee.

Working for Apple was my dream job, so I said, “Yes.” But, I still needed to fill out an application and formally apply. Later, I was attending a conference at the same time as a few of the hiring managers. I remember walking past a massive line of students queued up in the hall outside the Apple suite at the event. People glared at me, thinking that I was jumping the line.

I slipped past everyone, walked inside, and saw the hiring managers sitting there at the front. They smiled and said, “Hi Larry!” and took my job application and resume. The reality was it was a bit of a formality. I already knew they wanted to hire me, and they did.

Every single job I landed during my employed career came about due to connections in my network like this. I don’t share these stories to brag about how easy the process was. I’m sharing them because this strategy is available to you, too, and will make things much easier for you as well. Networking is a powerful strategy that will facilitate everything you need to do to accomplish your goals. I’ll talk about building a powerful network in a later chapter.

Ok, let’s move past these general strategies (which can help anyone succeed with whatever they want to do) and talk about more specific strategies that will help you reach the vision you have for your life.

Aligning your personal and professional visions

In chapter 4, you captured your long-term vision of an ideal future. What is it that you want most for your life? What did you write down?

Your personal vision:


You also defined your mission to make that vision come true. What did you decide your mission would be?

Your personal mission:


Now, it's time to align your personal and professional lives. We sometimes like to think we can draw a firm boundary between what we want in our personal lives and what we're trying to achieve in our professional lives.

But, it's so hard to split your energy and focus between those two worlds. It's even more challenging if those two visions are somewhat at odds. So, what happens?

Well, what most people do is prioritize their professional vision and defer their personal vision. They push their dreams into the future and hope they can return to them after retirement.

It doesn't work well. Sometimes, it doesn't work at all. As I shared earlier, a friend of mine delayed the pursuit of his personal vision, focused on his professional life, and wildly succeeded, but passed away before he could embark on the journey to achieve his personal goals.

I was doing much the same with my life. My personal vision was at odds with what was required to succeed with my professional vision. So, I ignored my personal life goals for decades.

Once I broke down the barriers between work and life, I was able to create a strategy for my professional life that supported the strategy for my personal life. Instead of working at odds with each other, they worked in harmony and let me live the life I want now instead of decades in the future.

So, let's take a moment and capture your existing professional vision and mission. What have you been striving to achieve in your professional career? What has been your mission to make that come true?

Your professional vision:


Your professional mission:


Your professional goals:


Now comes the hard part. Are there synergies between your personal and professional visions or not? Are your personal and professional missions working in harmony or not? Are your goals aligned? Write them side by side and evaluate them together.

Table of Personal and Professional Vision, Mission, and Goals

If things are out of alignment, how could you creatively adjust your visions and missions to focus all of your energy behind shared efforts to make both come true?

In my case, my visions were at odds with each other. My goals conflicted. Many years ago, my professional goal was to become a C-level tech executive in Silicon Valley and earn enough money to comfortably support my family with an enjoyable lifestyle. But, I realized I could never be fully satisfied working for someone else and making their vision come true instead of mine.

So, I adjusted my goals to pursue building my own tech startup. That enabled me to become a founder and CEO, build a team, and create products to pursue our vision.

However, these professional pursuits were still at odds with my personal vision of living in a cozy cabin in the mountains surrounded by a forest. I was stuck in the Bay Area, fighting terrible traffic on congested freeways every day, and not enjoying very much of my limited free time. My career path had trapped me in an urban world far from the great outdoors.

As I mentioned, a health scare woke me up. Was I going to defer my personal vision until it was too late? I couldn't let that happen. So, I went through this same exercise of aligning my visions and goals to find some way to make them all come true.

You'll find that you have to challenge all assumptions for this exercise to work. I asked myself:

  • Does my company have to be in Silicon Valley?

  • Does it have to be a "tech" company?

  • Do I still need to work in a tech career?

  • What if I pivoted my career and did something very different?

  • What could I create if I started my own business without the constraints I thought I had to work with? Where could I live?

  • At a foundational level, what was the Product of Me? What solutions could I offer? Who needs it? Who would want it?

  • What would a Business of Me look like that sold that "product"?

I deconstructed and reconstructed my visions to align them and then selected a strategy that I believed would support my mission to pursue the goal of making those visions come true. That's why I decided that if I wanted to live somewhere in the forest far away from the big city (and Silicon Valley), I would need to create my own "job" and build a flexible business that let me work anywhere in the world with anyone in the world.

My new professional goal to build this flexible, location-independent business is finally aligned with my personal goal to live wherever I choose. This lifestyle was simply not possible with the old professional vision that chained me to a specific geographic location.

So, now it's your turn. What is a bold potential professional vision that might also enable your personal vision to come true?

Your new professional vision:


What is the professional mission associated with your new vision? How can it potentially be more fully aligned with your personal mission?

Your new professional mission:


Given this new vision and mission, what professional goals do you want to pursue?

Your new professional goals:


Now, it’s time to craft a few strategies that might support your pursuit of these goals. Remember, your strategy is how you will navigate the competitive and challenging landscape to ensure the achievement of your tangible goals and your long-term vision. It will help you overcome obstacles, slip around barriers, remove blocks, and win.

Potential strategies to achieve your new goals:

Which one do you think might be your winning strategy? Let's put them to the test to identify the winner.

How well do your strategies help you overcome obstacles?

Let's put your strategies to the test. Evaluate the strength of your potential strategies in light of the obstacles you might face in pursuing your goals.

Have you identified all of the obstacles in your path? You captured some of them in chapter 5. But are there more barriers you might face when pursuing the strategies you just wrote down?

How does each potential strategy account for those obstacles? What will overcome blocks? What might break down the barriers?

Also, competition is always a concern. Whether your strategy involves being employed by a company or building your own business, you will be competing with someone else. How does each of your potential strategies deal with competition? Does one rise to the top?

In my case, I faced numerous issues with the original strategies I brainstormed. As I evaluated each one, the winner became increasingly apparent.

That doesn't mean the winning strategy was the "easiest" to pursue or the least risky. It certainly wasn't. The other strategies were more familiar and easier to execute. But, they failed my tests for different reasons. For example:

  1. Stay in my current career and find a tech job in a city within commute distance from our new country home.

    • FAIL: The nearby tech jobs were with companies I wouldn’t enjoy joining. Also, the last thing I wanted to do was reintroduce a long commute and risk my health and well-being again.

  2. Leave my career and find a non-tech 9-5 job in our small town.

    • FAIL: The available employers in my small town viewed me as overqualified, and the income wouldn't be enough to support my family.

  3. Find a tech job with a company that would be ok with me mainly working remotely but would require travel to work in the home office every month.

    • FAIL: This was before the pandemic. No tech employer wanted an organizational leader who worked remotely. I also didn't want to travel so far and be away from my family that much again.

  4. Launch another tech startup and find partners and employees who would also be comfortable working remotely.

    • FAIL: Founding another startup after my previous one failed would be very challenging since I would have to convince another set of investors to believe in me and the idea. Also, the market at that time wasn't great for fundraising. My current investors had already decided they were done.

So, that's why my winning strategy was building my own business that didn't require investment, could be run solo, would immediately generate revenue, and was location-independent to allow me to work from home (or anywhere).

Does one strategy stand out as you evaluate your strategies in light of your obstacles, blocks, and barriers? Which one has the greatest chance of success?

What is your best strategy?



Now that you’ve selected a winning strategy, it’s time to change gears and think about what you need to execute your strategy. Your focus will shift inward, focus on what is within your control, and plan the necessary steps to start making things happen.

What will help you achieve your goals? What do you need most? Some of the resources people often identify include:

  • Training, knowledge, skill acquisition, relevant experience.

  • Education, degrees, certifications.

  • Money, investors, advisors, partners.

  • Networking, connections, introductions.

  • More free time to focus on those goals!

However, one of the most critical resources you will need is your plan for how you will execute your strategy and make steady progress to achieve your goals. That’s what we’ll dive into in the next chapter.

Key Takeaways

  • Building an invincible version of you requires creating the right strategy to help you achieve your biggest goals.

  • Strategy and planning are not the same. Strategy is what you will do, while planning is the detailed “how” of executing that strategy.

  • If you don’t align your professional and personal goals, the conflict can pull you in two separate directions and derail your overall success.

  • Your strategy is how you think you will successfully navigate the rocky landscape between you and what you want to achieve (e.g., defeating the competition, knocking down barriers).

  • Don’t move into the planning phase until you select what you believe will be your winning strategy.

  • It’s good to have backup strategies if your hypothesis is wrong.

I’m looking forward to sharing more of my book with you this year! Become a premium subscriber today to keep reading the draft chapters as I complete them.

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I've really been enjoying the Invincible Career newsletter by Larry Cornett (@cornett). If you want to get ahead at work and be happier in your job, but you aren’t subscribed yet, you’re missing out.

Larry Cornett is a leadership coach and business advisor who hosts a private mastermind community for ambitious professionals with weekly challenges, office hours, and confidential support. If you’re interested in starting your own business or side hustle someday (or accelerating an existing one), check out his “Employee to Solopreneur” course (launching later this year).

Larry lives in Northern California near Lake Tahoe with his wife and children, and a gigantic Great Dane. He does his best to share advice to help others take complete control of their work and life. He’s also on Twitter @cornett.

Invincible Career®
Invincible Career - Claim your power and regain your freedom
Claim your power, regain your freedom, and become invincible in your work and life! I share professional advice, challenges, and tips to help you create your Invincible Career®.