The $84,257 Strategy to Achieve Impossible Career Goals in 2015

Flying To the Goal

In 2014, I took on the impossible task of placing bartenders, cashiers, and liberal arts students into high level positions.

If I was being realistic, it would have taken me the entire year just to coach these students up to entry level jobs, earning $10,000 – $15,000 more than their current positions.

Instead, I took on 3 premium students in 2014. When I totaled up all of the easily quantifiable wins that they got from ,using this process, I counted $84,257 in raises, promotions, and new jobs that they made THIS year.

Today, I’d like to show you the process we used to achieve these impossible goals. The secret to the process is that it goes beyond simple advice like “Make your goals specific,” and instead, leaves you with a step by step plan to set and achieve impossible career goals.

Figure Out Where You Are

2014 Inventory

One of the problems that most “goal setting plans” have is that they have you set goals without any thought to where you’re currently at.

To start, you’re going to create a document that takes a look at exactly where you are currently in your career, and what you accomplished in 2014.

List out:

  1. Key Metrics – What are you tracking in your career or business, and what were your numbers for 2014?
  2. Skills – What new skills did you learn this year? What skills did you maintain or improve? What skills did you let atrophy?
  3. Accomplishments and Projects – What are you most proud of from 2014? What did you accomplish that others could not? What projects got pushed to side or didn’t get the attention you had planned?
  4. Brand and Credentials – What did you do to get your name out there and create crediblity for yourself in 2014? What may have tarnished your reputation?
  5. Network – Who did you meet in 2014? How is your relationship with your coworkers and others in your industry?

The goal is to be objective about where you are. None of these things should be considered “failures” – instead, view them as information and growth opportunities for 2015.

You can also download the workbook if you’re interested.

Figure Out Where You Want to Go

2015 Goals

The next step is to determine where you’d like to go in your career. It helps to have a good idea of what you value and what you’re good at (more on that here). Then take a look at your “Where I am” document and ask yourself this:

“What’s the biggest change I could make this year to live my values and increase my impact?”

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Is it a new job? A raise or promotion? An increase in key metrics?

If you have more than one answer that’s fine… but have no more than three. If you want to achieve an impossible career goal, focus is paramount. You’ll want to also consider how difficult your goals will be; building a career graph can help.

Once you’ve figured out where you want to go, you’ll have to figure out how you’ll know when you achieve it. This should be objective criteria that you can look at to say “Yes, I made it” or “No, I didn’t.”

What resources will you need?

2015 Resources

The key insight here is that almost any career goal can be achieved with the same basic four ingredients.

  1. Accomplishments and Projects – What do you need to create and accomplish?
  2. Network – What connections do you need to make?
  3. Skills – What do you need to learn?
  4. Brand and Credentials – What do you need to do to increase your crediblity?

To start, create a list of what you’ll need in each category that will allow you to achieve that ultimate goal.

Check Your Assumptions

For every resource you’ve listed, you’re going to ask yourself a simple question: How could I achieve my ultimate goal without that resource?

For instance, a common one that my students list under credentials is a college degree. However, if we ask the question: “How can I get this job without a degree?” we often find that there are other brand indicators they can acquire that will allow them to achieve their goal faster.

Map the Path to Your Goal

We’re going to use a tool called a flowchart to create a broad plan for our 2015 goals. I recommend a computer program called CMAP tools, but you can also do this with a pen and (very large) piece of paper.

To start out, put a goal with “Where I am” on the very left of the page. On the very right of the page, put your “Where I’m going” goal.

Draw a circle around the two goals (these circles are called “nodes”). Then draw another node in the flowchart called “Tomorrow”, which you’ll connect to your “Where I am” goal.
Flowchart Where I am and Where Im going

Add in Your Resources

Take the list of resources you made above and make each resource a separate node on the flowchart. All of these nodes will connect directly back to your “Where I’m going” goal.
Flowchart with Resources

Work Backwards

Starting from the ultimate resources we need, we’ll work backwards asking ourselves two questions. The first is “What do I need to do to acquire this resource?”

For instance, if I ask myself “How can I get connections with 30 big name bloggers?” I have 3 thoughts that immediately come up:

  • Attend 2 Blogging Conferences
  • Make 50 comments on Other Blogs
  • Write 20 Cold Emails

I’ll add these to chart, and connect them to the next node.
Flowchart How can I Get This Resource

Then, I’ll ask myself “Can I do this tomorrow?” If so, I’ll go ahead and connect it to the “Tomorrow” node. If not, I’ll repeat the process above – asking myself “What do I need to acquire this resource?” and adding these steps as new nodes.Flowchart One Road Completed

What if You Don’t Know How to Acquire the Resource?

Sometimes, you’ll get to a step and simply don’t know how to proceed. For instance, I know I’ll need to connect affiliates (partners) to promote my product, but I don’t know how to do that.

In that case what you’re going to do is put a question mark in the flowchart, like this:
Flowchart with Question Mark

But that’s not all you’re going to do. Instead you’re going to bridge the gap to the question mark with two steps:

  1. Research
  2. Experimentation

For instance, if you don’t know how to add a hiring manager to your network, your flowchart might look something like this:

  1. Find 3 internet articles on how to connect with hiring managers
  2. Experiment with top two techniques on hiring managers, and see which one has better results.
  3. ?
  4. Connect with hiring managers

In my case, I have a friend named Kevin who does consulting on the topic of affiliate marketing, so the image looks like this:
Flowchart with Research and Experimentation

Complete Your Map

Using the tactics above you’ll continue creating nodes until every single node has a link to an action you can take tomorrow.
Completed Flowchart

You should now have a complete path to take, starting from actions you can take tomorrow, all the way to your formerly “impossible” goal.

The only thing left to do is follow it.

Make It Easy to Follow Your Path

HabitRPG Screenshot

The final step is to build a system that will propel you along your path.

To do this, you’re going to incrementally change your daily routines and systems until you can’t help but make progress on your goal every day.

One of the biggest things you can do to ensure success in this arena is to start small. A good rule is to make one (and only one) of these changes to your habits and systems every 2 – 4 weeks.

Here’s what you need to build into your system:

Carrots and Sticks

Flying To the Goal

One of the first systems to do is make it very painful to do the wrong thing and very pleasurable to do the right thing. This is a force multiplier, as it makes all subsequent habits easier.

Different things are painful and pleasurable for different people. Some people love earning points, some people hate losing money, and some people hate letting someone else down. That’s why it’s important to experiment with the following systems and see what works for you:

  • Meet weekly with a coach or accountability buddy who is proud when you do the right thing, and disappointed when you do the wrong thing. (I go the extra mile with this and actually pay my students $20 to show up.)
  • Use HabitRPG to earn points and experience when you do the right things, and lose health and items when you do the wrong thing.
  • Use Beeminder to charge you money when you get off track of your habits.
  • Check off actions in Todoist and watching your karma number go up.
  • Taking a moment after doing the right thing to feel proud and appreciate what you accomplished.

A Proactive Mindset

The next habit you should build is a habit of being proactive and excited for work. It might seem funny to call this a habit, but you fall into habits of thought just like you fall into habits of action – you can’t fix one without fixing the other.

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Here are a few of the mindset shifts you might want to make:

  • Change all thoughts of “I have to” to “I choose to.”
  • Change the thought of “This is such a big goal” to “What’s the very next action to take?”
  • Change the thought of “I don’t have this skill” to “How can I learn this skill?”
  • Change the thought of “I’m a fraud” to “I deserve this.”
  • Change the thought of “I can’t wait to tell people what I’m doing” to “I can’t wait to show people what I’ve done.”

A Productive Environment

Focus@Will Screenshot

The next step is to set up a specific environment and time for focused and productive work. This habit involves making a checklist of your unique productive environment, and checking it off before you begin. This alone can dramatically increase your productivity.

Here are some hints:

  • Create a home office, find a coworking space, or identify an awesome coffee shop.
  • Take a couple minutes before you start to tidy your workspace, get what you need, and center yourself.
  • Put on music that helps you focus and makes you motivated. (I use Focus@Will.)
  • Close everything on your computer (including browser tabs) that aren’t needed for the task at hand.
  • Use an accountability system such as the Lesswrong Coworking Chat.

A System for Focus and Recharge

The next step is to create a system for working in focused bursts, followed by periods of recharge. This allows you to avoid burnout and kills the destructive mindset that work and play are at odds (they’re actually synergistic).

Here’s some hints:

  • Take a look at some of the systems already out there for this, such the Pomodoro Technique, (10 + 2) * 5, or 60-60-30.
  • Figure out what your “time sucks” are, such as Facebook, email, or daydreaming. Make sure to catch yourself when you use these activities during your productive time, and schedule them only during your recharge time.
  • Make a list of the activities that recharge you mentally, physically, spiritually, and emotionally. Figure out what aspect of your psyche is burned out, and use them strategically during your recharge times.

Your One Must-Do Task

Make a habit of figuring out what your top priority is, and working on that first. What’s the one thing you can do that will most move you forward on your flow chart?

Here are some ways to figure out your must-do task:

  • Ask yourself what you would do if your life depended on achieving your goal as quickly as possible.
  • Ask yourself what next action is most scary to you – this often intersects with important tasks that you’ve been avoiding.
  • Calculate the expected value of each action, and choose the one that’s the highest.

Contingency Plans

Contingency Planning Table

It would be great if you could simply follow all these habits and execute your plan without a bump in the road – but as you know, that almost never happens. Life always has other plans. What all great sports coaches know is that even the best laid strategies and plans will need adjustment. So just like a coach, you’re going to create a playbook of different plans you can use in reaction to the roadblocks life throws at you. Instead of expecting perfection, you’ll learn to plan for imperfection by using a technique called the pre-mortem.

Imagine it’s December 31st, 2015, you’re looking back on your year, at your well-laid plans – and you’ve failed! Now ask yourself this question: What went wrong? Were there areas of your map that proved harder than you expected? Maybe you got sick at some point, and found it hard to continue your habits when you got well again. Perhaps you found that as work demands increased, you weren’t able to focus on your own agenda. List out every single thing that could have gone wrong to lead you to this faiulre

Using that list, you now know what might derail your plan. However, this doesn’t help you to achieve your goals, so the next step is to create contingency plans for each of the possible failure points you identified, known as implementation intentions. These are simple if-then statements that tell you what to do if you run into a road block. For instance:

“If I find myself getting burnt out from all the work – then I’ll take a day off to recharge and do yoga.”

Here’s another:

“If I find myself procrastinating on going to a networking event, then I’ll call a friend on the phone before I go, to get myself into a social state.”

As you can see, implementation intentions are a powerful way to expect roadblocks, and succeed anyway.

However, even if you have the intention to use your plan, that doesn’t mean you’ll think to use it in the moment. That’s why you’re going to spend a couple weeks visualizing yourself enacting your intentions. With the yoga example above, you would visualize what it looks like when you get burnt out. What situations arise in your life that lead to burnout? What does it feel like in your body? What does it look like? Then, you’re going to visualize yourself calling in to work, taking a day off, and going to the park and doing yoga. It should take you 10-15 minutes every day for a couple weeks to visualize all your implementation intentions, which will make you much more likely to remember and use them when the time comes.

So as a quick recap, here are the steps to creating contingency plans:

  1. Create a pre-mortem of why you failed at your goal.
  2. Create implementation intentions for what you’ll do to counteract each failure point.
  3. Visualize each implementation intention for 2-3 weeks, 10-15 minutes a day.

Choosing More Habits

It turns out that there are only ever five types of habits, skills, and systems that we should focus on. (I have another post coming out on this that gets more into specifics.) I’ve given you a list of force multipliers above, but once you’ve run through those, take a look at the list below to choose your next habit:

  • Force Multipliers – What could 2X, 10X, or 100X your acceleration towards your goal?
  • Minimum Viable Skills – What are the habits and skills you actually need to achieve your goal? If you don’t have these habits, it’s impossible to get from where you are to where you want to be.
  • Bottlenecks – What’s the slowest part of your process? What habits or systems could you create to remove these bottlenecks and speed up everything else as a result?
  • Competitive Advantages – What habit, skill, or system could you specialize in and be the best in the world at? Creating these is one of the fastest ways to achieve impossible career goals.
  • Future-proof skills – What habits, skills, or systems will allow you to not only achieve your goals this year, but also remain competitive for the future? It’s this focus that separates careers amateurs at the whims of industry trends, from professionals who create their own career destiny.


If you follow this process, I can almost guarantee that you’ll see leaps in your career that you didn’t think possible. I’ve seen it over and over again with my students.

That’s why I created this free workbook. Simply follow along day by day and by the end of the year, you’ll have achieved your impossible career goal.

Click the link below to check it out.

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