Invincible Career®
Invincible Career - Claim your power and regain your freedom
Book Chapter - Making Your Achievable Plans (Issue #381)

Book Chapter - Making Your Achievable Plans (Issue #381)

A goal without a plan is simply a dream

Most people never reach this step of making an actual plan.

They dream, and they might even brainstorm strategies, but they don’t take the next step. They never create a concrete plan to achieve their most important personal goals.

If you remember the study I mentioned in chapter 7, creating a plan for how you will accomplish your goal improves your probability of success. Your odds rise to 50%.

That may not seem inspiring. But, 50/50 odds are much better than no chance of success at all. Plus, as you continue to work through the remaining chapters in this book, your odds of success will continue to improve.

So, how do you feel about planning? Which one of these quotes resonates best with how you think about it?

  1. “Remember, if you fail to prepare you are preparing to fail.”
    — Reverend H. K. Williams

  2. “Good fortune is what happens when opportunity meets with planning.”
    — Thomas Edison

  3. “Just because you made a good plan, doesn’t mean that’s what’s gonna happen.”
    — Taylor Swift

  4. “The reason that everybody likes planning is that nobody has to do anything.”
    — Jerry Brown

As you may have guessed, I’m a planner. For as long as I can remember, I’ve created plans for what I want to achieve. I know that everything I want won’t simply fall into my lap.

However, I know many people who are not like me. They’ve told me that, until this point, their life has just “happened.” Of course, they’ve moved forward in life. But they didn’t plan very far ahead, or they followed along with someone else’s plan.

At some point, this approach fails. Life won’t always give you what you want or need. Also, someone else’s plan may not have your best interests in mind. One day, you may find yourself dissatisfied or unhappy, but you won’t know what to do about it because it all just “happened.”

I’ve worked with many clients who end up in this situation. So, we create plans together. They execute the plans and they see results. For the first time, they are choosing their path in life and they’re amazed by how much better that is than just being tossed around by the winds of fate.

Life is better when you’re in control of your destiny.

Invincible Career® is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Plan for uncertainty

I’m going to propose a different approach than traditional planning. What I like to do with my clients is a mix of planning techniques that are inspired by:

  • Research on “reverse planning.”

  • A flexible strategy of milestone hops. 

  • Decades of my life spent in business planning meetings.

Reverse planning

If you are clear about your big goal and set your intention, you can start planning backward with the steps that make it achievable. Researchers studied this “reverse planning strategy” and found that, for more complex goals and tasks, it is more effective and enjoyable than traditional chronological planning.

“True retrospection is used to review events that have already happened, but using one’s imagination to think of future events as if they were in the past facilitates visualization of both the end goal and the steps required to get there. This ‘future retrospection’ tends to increase the anticipation of pleasure from achieving the goal and helps bring about goal-directed behaviors.”

Planning forward can feel overwhelming when your goal is ambitious. It is too hard to imagine all the tasks you must accomplish between now and then. I found this to be true in my own life.

Planning backward helped me see it all as achievable. I started with the assumption that I had accomplished my goal (e.g., I’m living in my home in the mountains).

Then I defined the logical step that must have taken place right before that. I asked and answered a series of questions to determine each move.

  • Why am I able to live there?

  • How could someone there make a living?

  • How could someone like me do that for a living?

  • What did I have to do to make that possible?

  • How did I prepare for that?

And so on… continuing to plan backward until I reached what I thought would be my next logical step right now. You can use the same process. Start with your long-term goal and start planning backward year by year — at a high level, of course — to get a sense of what you may need to do to get there.

Milestone hops

We don’t know what we don’t know. We can’t predict the future, either. But, you defined your most audacious goals in chapter 7, which should have given you a vision of an outcome you desire for your life.

Reverse planning can help you envision a series of high-level steps to make that vision come true, but it probably left you with a few burning questions:

What do you I do now?

What is my next step?

I know it can feel like a paradox of choice. There are almost infinite possibilities, moves, and tactics you could choose to employ right now at this current point in time. There are so many paths you could take to navigate that competitive landscape to reach any number of goals.

You already defined a strategy for navigating that landscape and overcoming barriers and obstacles. It sure would be nice if your path was a straight and narrow one, as illustrated below. Choose a goal, choose a starting point, plan your path, and just get going. Right?

In a simpler world — and life — goals wouldn’t change and we would never have to deviate from our planned path to get there. But life is chaotic and we know nothing is ever as simple and easy as we think it will be. Without a plan, you may end up being lost in the twists and turns of reality.

However, there is a more effective strategy and flexible approach:

  • Start somewhere (it doesn’t have to be perfect).

  • Choose a path.

  • Identify your first milestone.

  • Make the “hop” to get there (e.g., complete projects and tasks).

  • Gather data, assess, and reevaluate.

  • Course-correct and adapt your strategy if necessary.

  • Identify your next milestone and continue.

  • Your vision will be on the far horizon.

  • Your goals are what you need to achieve that vision.

  • Your strategic plans help you accomplish those goals.

  • The tasks are what you need to do to execute those plans.

Business planning

No plan survives first contact with reality. Yes, you need a plan. But accept that you will always need to re-plan.

“Peace-time plans are of no particular value, but peace-time planning is indispensable.”
— Dwight Eisenhower

In the corporate world, we had rough one-year plans, more realistic six-month plans, detailed quarterly roadmap plans, and very specific project plans. More often than not, our longer-term fuzzier plans either changed radically, or we abandoned them entirely. 

The world and the competitive landscape are not under your control — they change frequently, and chaos often alters them. A plan is an attempt to predict the future, but you can’t predict the future. 

Perhaps one way to visualize this reality is to picture life as a large, rushing river full of twists and turns, obstacles, and rapids. Your long-term goal is your destination somewhere along the course of this river. But, rather than a precise destination (e.g., I want to bring my boat ashore at that exact rock at those precise geo-coordinates), your goal should describe a desirable outcome that could be possible at multiple destinations. 

The farther away your goal is, the fuzzier your view of it will be and the more vague your long-term plans will be. They exist at the far end of a broad cone of possibilities. Your strategy is how you plan to navigate the course of the chaotic river to get there. As you get closer, you will narrow in on the place you want to come ashore. 

But the waters you are traversing with your boat right now require a crisp and detailed plan. You need to know precisely how you will paddle around the rock in the river in front of you. You need to aim your boat to navigate the rapids that are just ahead. 

So, it’s ok to have fuzzier, placeholder plans for the far future. Don’t even bother with creating detailed plans for that timeline because everything might change — and probably will. 

However, you do need precise plans for what you are doing today, tomorrow, next week, and in the months ahead. Some plans will have activities you must set in motion now. They will be captured in the projects you define.

Define projects

A project is composed of the tasks you need to complete over time to achieve a goal. You'll notice that each project is a mini version of how you're thinking about what it will take to achieve your most important long-term life goals. 

Deconstruct your strategic statement and ask questions for each component. For example, if your strategy is to be "uniquely valuable," what can you do to be unique? 

The details will be crisp and well-defined for your near-term projects. You may even be able to plan the daily tasks you’ll need to make progress and accomplish them.

However, things get a bit fuzzier as you consider the projects you need to execute your strategy a year from now. Your plans will become more general as you forecast even further into the future, two to five years from now (e.g., “Write my second book”). And, things will become fuzzier still as you consider the projects that will support your long-term vision you don’t expect to reach for 10-20+ years.

A project definition will include:

  • Overall goal

    • What do you want to accomplish? 

  • Success measures

    • What does success look like?

    • How will you know when you've successfully completed the project?

  • Requirements

    • What are the expectations?

    • It's helpful to think in terms of must-have requirements and nice-to-have requirements.

    • For example, resist the urge to build the Taj Mahal when a cozy cabin will meet your needs (i.e., the requirements). 

  • Resources

    • What will you need to complete the project successfully?

    • This could include other people, certain skills, materials, money, etc. 

  • Dependencies

    • Does this project depend on any external factors (e.g., something or someone must be available before you can begin)?

    • Does it depend on a previous project to be completed first (e.g., the output from an earlier project is an input into this project)?

  • Scope

    • How long do you estimate this project will take?

    • Is it time bound (i.e., the project must be finished by a specific date)?

    • Or, is it based on a milestone (e.g., the first version can be completed and launched, then improved later)?

    • As you may have already experienced, almost every project may take twice as long and costs three times as much as you think it will. 

  • Dates

    • When do you want this project to begin?

    • How long will it last, based on the scope of the previous step?

    • When do you expect you will finish the project?

Let's use an example. If you wanted to build and launch a simple website to promote yourself, here is one way you might define that project. 

Overall goal

  • Launch a website that will attract potential hiring managers and recruiters.

Success measures 

  • You get five friends to review the site and provide positive feedback that it’s ready to launch.

  • The website is functional and available.

  • Google Search can crawl and index the site.


  • You're satisfied with how the website looks in the most commonly used desktop web browsers on MacOS and Windows. 

  • You're satisfied with how the website looks in the most commonly used mobile web browsers on iOS and Android. 

  • The site loads quickly enough to not be annoying, all pages on the site load as expected, and the website doesn't generate any errors. 

  • People can navigate and browse your site, learn about you and what you do, access links to your other online profiles, and successfully send you a message to contact you. 


  • You'll design and customize the site yourself using WordPress. 

  • You'll use free images from Unsplash. 

  • You need a domain. 

  • You need a hosting provider. 

  • You'll need some money to pay for initially registering the domain and the monthly website hosting fee. 


  • You'll need a hosting provider that can host a WordPress site. 

  • You'll need to think about the name you want for your website. 

  • You'll need a unique name that is available for your domain. 


  • You can only work on the website for about 6 hours every weekend. 

  • You estimate you can complete the total project in 4 weeks. 


  • You can begin working on the project next weekend. 

  • Given the scope, you estimate a completion date on Saturday during the last weekend of next month. 

  • You'll announce and share the website on your socials on the following Monday morning. 

Given the amount of detail and work that goes into defining a project like this, you should only create detailed projects that must be completed to achieve your near-term goals for the next few months. Don’t even bother with detailed plans or project definitions beyond a year. Life is too unpredictable. I think we’ve all realized how much our lives can be completely disrupted beyond anything we might have imagined.

That’s why, decades ago, my plans and projects for my distant future were quite vague. I knew what my long-term vision was for my life. I had some long-term goals. But, the big projects to support them were high level:

  • Start my own business.

  • Move somewhere into the mountains.

  • Write a book.

You can pencil in high-level project ideas for your longer-term goals, of course. But, don't overload yourself and become overwhelmed with defining and committing to too many projects at once. 

What high-level projects are you planning this year to accomplish your biggest goals for the year?

What is the more detailed list of projects that you will focus on for the next few weeks and months?

As a next step, use the project definition framework that I described above for each of the projects you want to work on soon. As you begin and learn more, you can flesh out more details and make adjustments to your project plan as necessary. However, let’s take a moment and make sure the projects are aligned with your strategy.

Ensure strategic alignment

It’s easy to get lost in the weeds when you start defining projects and working on them. So, now is the time to ensure alignment with your strategy. You want to make sure you’re using your time and energy wisely.

You can ask a few questions to double-check that you’re working on the right things:

  • How will the successful outcome of these projects support my strategy?

  • Will these projects “move the needle” to get me closer to my goals?

  • Are the investments of time, energy, and money worth the result they should yield?

  • Do the projects complement each other or not?

  • Am I sequencing these projects correctly?

That last question is where your roadmap comes into play.

Create your roadmap

A roadmap is an overview of your projects mapped into a calendar view. One of your roadmaps could be a “vision roadmap” that reflects your long-term life vision and goals. There will be no specific project details, but it does provide a sense of sequencing and timing over years. For example:

Vision Roadmap
Vision Roadmap

In the example above, note the high-level goals, tasks, and aspirational outcomes. I included a task of “Plan move” instead of something too specific, such as:

  • Move to the Rocky Mountains.

  • Move to Aspen, Colorado.

  • Move to a four-bedroom, two-bath blue house 5.7 miles west of the Aspen County Airport in Aspen, Colorado.

The items on the long-term roadmap do not include specific details. If you’ve created your long-term vision and goals correctly, you won’t need to change them frequently as things change in your life and the world around you. At this level, a detailed plan or roadmap that is too specific won't survive the chaos of reality. So, don't bother.

However, you should also create a more specific one-year roadmap that lays out the projects you want to focus on to accomplish your most important goals for this year. Now, this will include more detailed projects than a vision roadmap. But, it is still not a detailed breakdown of any single project.

One-year roadmap
One-year roadmap

What are the timing, timeline, and effort required for each project? What can you work on in parallel (given your available time and resources)? Which projects must you complete before other projects can begin?

Finally, create a detailed roadmap view for each project you want to work on now. Identify the tasks and activities you will focus on each week for the duration of the project. What tasks can you complete in parallel? What tasks must you sequence?

Project Roadmap
Project Roadmap

Note: The companion website for this book has resources, which include downloadable spreadsheets and templates to help you build your own roadmaps.

Establish milestones

Your milestones will be the smaller goals you want to reach on the journey to your larger long-term goals. They mark the completion of major project tasks and the ends of various phases. You’ll find that milestones will probably map to the subgoals you identified in chapter 7.

For example, you might have a long-term goal to have one of your books on The New York Times Best Seller list. But, it is exceedingly rare for an author to have their very first book achieve such recognition. So, you would probably want to set milestones for publishing your first few books along the way.

You captured your most audacious goals in chapter 7. Now, it’s time to identify some key milestones for those goals that will help you assess your progress. Review your subgoals, since they will inform your milestones.

A good way to think about this exercise is to visualize a journey. If you were currently in Los Angeles and your long-term goal was to reach New York City, what cities would be milestones on your route to get there? Your travel strategy determined your mode of transportation and informed the route you will take. Knowing this, you now can plan the cities you must pass through to get where you are going.

Similarly, your milestones are what you must achieve to get where you are going and reach your long-term goal. You can check them off as you make progress. This will give you more confidence and assurance that you’re on track.

What are some key milestones for your highest-priority long-term goal?

What are some key milestones for the biggest goals you want to achieve over the next two to five years?

What are some key milestones for the goals you want to achieve this year?

If you’re struggling to identify milestones, it might help to bounce some ideas off a good friend. Or, you can talk with me and the members of my community. Many of us have spent years of our careers in project planning meetings and exercises.

Leverage checkpoints

Checkpoints help you measure progress. Milestones are also certainly major checkpoints, but you will need additional smaller checkpoints to identify tasks you must complete on the path to a milestone. The more frequent checkpoints you define will be quite useful to assess progress, but they aren’t the same as your key milestones.

In the book example above, publishing a book is a key milestone, but you would require dozens of checkpoints to stay on track and publish that book. Writing and editing a book is a long and complex process.

A few simple examples of checkpoints:

  • A weekly review of total pages written.

  • Finish the first draft of your book.

  • Proofread and edit the book.

  • Have an editor review the book.

  • Get feedback from beta readers.

  • Come up with the right title.

  • Format the book for publication.

  • Hire someone to design the cover.

  • Get your book website ready.

  • Create a book launch plan.

You can create a list of checkpoints and work through them yourself. You can even establish a schedule and process to review your checkpoints by yourself.

However, as I’ve mentioned before, accountability partners improve your odds of success. You could schedule regular checkpoints to review progress with an accountability buddy, coach, or community.

What are some checkpoints you will need to assess progress toward the key milestones you identified for this year?

You will definitely have way more checkpoints for all the tasks you’ll need to accomplish your goals for the year. But, this should give a small taste of what it’s like to define them.

Create backup plans

I’m not sure why some people proudly proclaim that they don’t have a backup plan. They say that the idea of having backup plans in life is silly. You have to go all-in on what you do. Win big or fail spectacularly!

The problem is that you are never entirely in control of the variables that influence outcomes. Even if you are entirely in control of that big long-term goal you’ve defined, you don’t control the world around you. It’s safer to assume that something will go wrong because life is unpredictable.

It’s only smart to have a backup plan, just in case things do go sideways. It’s actually not a bad idea to have a series of backup plans; Plans A-D.

Plan A 

Plan A is your current plan, which is what you’ve been defining above (e.g., the roadmap, milestones, and checkpoints). This is how you plan to execute your primary strategy to achieve your goals. Of course, it should be where you are focusing most of your time and energy.

Given your best planning and thought, this path is the one that you think will yield the outcome that you want. However, your plan could go sideways if an unanticipated wrench gets thrown into the works.

Plan B 

Plan B should be your strategy for a course correction if Plan A goes wrong at some point. What do I mean by things going wrong? Some examples:

  • A re-org removes the potential promotion path you were counting on.

  • The country goes into a significant recession.

  • A pandemic changes the world around you.

Sometimes your Plan B works out even better than your Plan A would have if you had tried to stay the course.

What is your Plan B?


Plan C 

Plan C is a complete change of strategy. What you were trying to do to reach your goal will no longer work at all.

I activated my Plan C when I left the Silicon Valley tech world and launched my career coaching business. What I do is somewhat related to my old career, but it is very different from my previous roles, and it has required significant planning and experimentation.

What is your Plan C?


Plan D 

Plan D is your emergency plan when everything goes wrong. It is what you fall back on when something extremely disruptive occurs. For example, the economy collapses, you lose your job, and you’re on the brink of bankruptcy.

It is a rare occurrence, and it’s nice to think that this will never happen to you. However, there are no guarantees in life. Recessions, depressions, and pandemics don’t care about your plans.

When everything fails, and you need to go into survival mode for a while, Plan D will keep you going. For example, I have my eye on a job at my favorite local hardware store (I love tools). Worst-case scenario, I could move in with a family member until I got back on my feet.

What is your Plan D?


You may think, “What’s the point of making these backup plans now? I’ll just figure things out later if something goes wrong.

First, it is almost impossible to think clearly and plan well when you are in the middle of an emergency (e.g., you were just fired). Sometimes people end up making a decision too quickly and regret it later. They didn’t take the time to plan and research, so they end up getting into an even worse situation.

“The time to repair the roof is when the sun is shining.”
— John F. Kennedy

Second, successfully planning your next move takes time, especially if it’s a significant change of plan. Some people have the luxury of a large financial cushion and can take several months or even years to figure out their alternative path. Many people do not and cannot.

Third, even when you have a backup plan, getting back on track always takes longer than you think. If you need even more time to figure out your next move, it will create a significant delay.

Commit to your plans

I don’t expect this chapter to teach you everything you need to know about planning, creating projects, and executing your roadmap. My goal here is to persuade you to invest in yourself and commit to making a plan to get what you want out of life.

Building the invincible version of you means you dedicate at least some of your precious time to pursuing your most important personal goals. How will you achieve what you want in your life if you never make time to work on it?

It’s great to have goals. It’s wonderful to have strategies for how you will pursue those goals. But without a plan, most people struggle to make serious progress. They shoot from the hip, and they eventually fail.

A plan gives you a fighting chance!

How to ensure progress

One of the best ways to ensure steady progress is to identify the daily and weekly tasks you need for your project work. For example, writing a book is a massive project. But blocking an hour each morning to write will ensure you conquer that project page by page every day. Establishing habits will ensure project tasks get completed. Let's tackle that topic in the next chapter.

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.

By the way, there is a great way you can support my work without spending any money on a premium subscription:

📣 Recommending my newsletter on social media! 📣 


It only takes a few seconds, and it helps grow my business so I can continue making time to write it.

I’ll even provide some copy and paste text to make it easy to share on Twitter, Reddit, LinkedIn, Facebook, etc. Thanks in advance!

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®.