Making Plans


Pull together everything you’ll use to make your professional brand.

Get your head in the game by considering what employers really want.

Make an outline of what you want in your career, and figure out “why” instead of merely “what”.

Connect the dots between your future desired career and past experiences.

Set immediate goals to attain that large-scale purpose, which should represent an ideal role.

Get ready to plan

Before anything, make a gigantic list of everything you could theoretically use for a professional brand:
  • Volunteer work and clubs
  • Professional associations
  • Jobs you’ve had, including part-time and short-term gigs
  • Non-work-related experience like volunteering, internships, job shadowing, and externships
  • All creative endeavors, hobbies, pastimes, and preferences
  • If you can’t think of anything then get out, volunteer and join some clubs.

The purpose of this list is to “prime” your mind for all the things you could do for a living and the things you seem to like doing.

A. Get in the right frame of mind

The job-seeking process is stressful, so continually manage your anxiety throughout the experience.

Take control of your career:
  • If you don’t manage your career, others will do it for you.
  • Your self-worth and long-term expectations determine your long-term limits.
  • Working hard doesn’t lead to a better life, but working hard on the right things does.

Your job does not have to be something you love:
  • Everyone needs money, but not everyone likes doing things that make much money.
  • Get a job you can stand, not something you’re dreaming of doing.
    • You’ll find much more meaning out of doing the work correctly, in the position you’re in, than in constantly seeking to find the right kind of work.
  • Examine your ikigai (i.e., “your reason for being”):
    • First, ask yourself key questions about what you do.
      1. What do you love doing?
      2. What are you good at?
      3. What does the world need from you?
      4. What can you get paid for?
    • Then, ask how those things converge.
      • Your PASSION is what you love and are good at.
      • Your MISSION is what you love and the world needs.
      • Your PROFESSION is what you’re good at and can be paid for.
      • Your VOCATION is what the world needs and you can be paid for.
    • Finally, ask what may be missing from what you do.
      • If you don’t love it, you’ll only ever find comfort, but with a feeling of emptiness.
      • If the world doesn’t need it, you’ll find satisfaction, but won’t feel any positive impact on the world.
      • If you’re not good at it, you’ll feel excited, but always uncertain.
      • If you can’t be paid for it, you’ll find fullness in it, but won’t get paid for it.
  • If you can do what you love, you’re very lucky, but you can still be satisfied with life in a job you don’t love.

Don’t worry about your present or future job title:
  • A job title only implies what’s in the job, but doesn’t fully articulate what you’ve done with it.
  • Your title is only the starting point to communicate what you’re doing with the job.
  • If you simply want a future title without a clear understanding of the responsibilities involved with it, you have no idea what you want in your career.

Careers are inherently unpredictable:
  • Successful people usually transition through many lateral career moves.
    • An unrelated part-time job or volunteer experience now might build out your career later.
    • Interview someone you know with what you imagine has a “stable job”.
  • Learn from others who have succeeded in their careers.
    • Note the chances, occurrences, run-ins, and meetings that led to their current position.
  • Look at job roles outside what you’re familiar with to gain the most long-term experience.

Many employers simply want someone to do what they tell them to:
  • The person must be intelligent or experienced enough to do the job, but doesn’t question their established methods.
  • You’re a valuable resource, and employers can only contract for specific parts of what you can do, so don’t expect to find a boss who will value you as much as a parent can.
  • No matter what, every job involves making your boss look good.

Even in a long-distance remote-work culture, face-to-face time is crucial to close a deal, so be prepared to travel.

If you do like your job, consider negotiating more pay before looking for a new one:
  • Prepare a compelling case for them with the last 6 months of results.
  • Schedule a low-stress time for the meeting, ideally after lunch on a Friday.
  • Negotiate carefully, since it could backfire and you may quickly need another job if your boss is offended.

Employers usually look beyond your business results

Every employer is using a roundabout approach to ask 3 simple questions to each candidate:
  1. Can you do the job?
  2. Will you like doing the job?
  3. Can we handle working with you?

Since you’d have to do the job for them to accurately measure your aptitude, they must rely on how confident you look in an interview.

A positive attitude that flows from satisfaction and success can cover experience gaps, but a bad attitude can blow any chance at a job.

Your culture must mix well with a company’s culture:
  • Your beliefs and values must at least somewhat match the company’s.
    • You don’t need to perfectly conform, but you should at least somewhat agree with the company’s “core values”.
    • Your ability to work at the same company comes mostly from how much you share their values, which will often change as you succeed.
  • There’s no “right” way to behave: even helpfulness or kindness is inappropriate in some cultural contexts.

Most job-seekers lie a little about their aptitude, so you must come across as more professional than you typically are to compete.

You can get almost any job you want if a hiring manager remembers your “soft” skills after meeting you:
  • Competence is more important than credentials.
  • Enthusiasm is more important than talent.
  • Since rejection is normal in the workplace, rise to the occasion.
  • But, if you’re forgettable, you ruin any chance for that job.

You’ll never be fully prepared for a job search, so plan ahead and push forward:
  • Job-seeking always comes with risks, but a career change is almost always a good decision.
  • Accept the inevitable changes that come, including things you couldn’t have expected.
  • You’re always safe if you know how to safely say “no”.

Remove any distractions from your search:
  • Job-seeking is a trial of consistent failure and rejection.
  • To thrive at job-seeking, you must self-respect and enjoy yourself to push back against the rejection, no matter what happens.

The rarest resources in your job search will be time and motivation:
  • Expect more restructuring, planning, and recuperation than you’d otherwise plan to need.
  • Throughout the job hunt, consistently consult your friends for emotional support.

B. Roughly sketch out your future career

Your dream job should have a few components:
  1. A workload you can comfortably achieve.
  2. Work you won’t feel terrible about doing.
  3. A great team you can work with.
  4. Opportunities for education and growth.
  5. Enough pay to sustain your lifestyle goals.

Take as much time as you need to think and brainstorm:
  • Discovering a new career is a focused creative effort.
  • To find what you’re good at, focus on what you tend to like doing in your free time for extended periods.
  • Ask your trustworthy friends, colleagues, and mentors their opinion.
  • Go on a trip somewhere new to clear your mind.

Take employment and personality tests to self-discover and consider what you naturally enjoy:

You must have something you’re passionate about in any future job, but don’t expect anyone to give it:
  • Focus on what you can do for them, not on how you can benefit from the job.
  • You don’t need a passion for the entire job, but you can always find something in that role if you creatively examine it.
    • Even if it’s a lousy job in a terrible industry, you can still find satisfaction in doing the best you possibly can in the midst of it.
  • A low-paying job with something you love is far better than a high-paying job you absolutely hate.

Figure out “why” you work instead of just “what”

No matter what, all sufficiently worthwhile jobs have the same components:
  1. The ability to make autonomous decisions for yourself (control)
  2. The freedom for you to fix problems as needed (creativity)
  3. The ability to influence others with your decisions (impact)
  4. What you’re good at and built to love doing (competence)
  5. Someone else doesn’t want to or can’t do it, so they’ll pay you to do it (demand)

Every job is a hybrid of only a few types of roles:
  • Entertainers express themselves to the public (hard to start in).
  • Creatives develop new artistic works (hard to start in).
  • Merchants buy and sell items at a profit (needs industry-specific knowledge).
  • Relaters connect people to other people and things (needs connections).
  • Brains critically think, analyze, and come to solutions (needs intelligence).
  • Movers make things happen and help people (needs strength and social skills).
  • Recordkeepers maintain and transmit information (needs thoroughness and patience).

Ask yourself deep, probing questions:
  • What were you doing when you felt a sense of flow?
  • What do you gravitate toward with your extra time?
  • What do you find meaningless and why?
  • Where do you find work meaningful and why?
  • If you could do anything, what would you do?
  • More than anything else, what one thing would you like to see in your career?

Discover your core values and beliefs:
  • Track your natural aptitudes and tendencies.
  • Find what motivates you the most.
  • Look into your past experiences and examine the conflicts that tore your feelings up the most.
  • Keep asking “what is my true purpose in life?” until you find something that makes you cry out of longing for it.

Draw out what you want to see yourself doing in 10-20 years:
  • Imagine three vastly different professional fields that excite you.
  • Detail the work activities, the preferred cities, and the scope of your work’s effect.

Before moving on, make a clear image of what you want out of your work:
  1. Write a detailed description of your future work.
  2. Describe the feelings and sensations you’ll experience.
  3. Mentally commit yourself to the experience and never sway from it.

Imagine work you can do that nearly everyone needs

Ignore what society calls a “great job”:
  • Your current life status and personality define what you’ll call a “dream job”.
  • There’s a tradeoff for every job:
    • A fun job is often not challenging, which will eventually bore you.
    • Stable jobs often give no chance of upward mobility or variety, which may make you feel oppressed or stifled.
    • Unstable jobs that pay lucratively may make you feel unsafe.
    • A powerful job often comes with many responsibilities you may not want.
  • Many positions requiring college degrees are incredibly low-demand.

You’re likely to enjoy any job once you’re experienced with it, with some exceptions:
  • Your skills aren’t particularly valuable or important, since many other people can do it.
  • The job itself is contributing to something that either has no impact or a bad impact on the world at large.
  • You have to work with people you really dislike.

Look for any jobs that represent universal human issues such as government conflicts, sickness, interpersonal conflicts, and death.

Find a currently unfulfilled need by asking questions about an industry that catches your attention:
  • Why does this industry exist?
  • What problems could the industry have fixed?
  • What are bold mavericks doing in the industry?
  • Who is winning in the industry?

If you want to work for yourself, start a business instead of looking for a new job.

Get input from others

To survive the job hunt, you must surround yourself with positive, encouraging people:
  • At least once a week, connect with them to re-energize yourself for the search.
  • High-quality friends give realistic, useful constructive criticism.
  • Ignore people who don’t care about your best interests.

Find a mentor:
  • Find mentors by requesting time from successful people for their advice.
  • Mentors are essential to both your growth and your job security.
    • The more influential your mentor, the more chances you’ll succeed.
  • Take the context of their advice from experts by the profession they’ve succeeded in.

Try to arrange mock interviews:
  • You need others’ input to succeed at the job hunt.
  • However, hiring managers are extremely cautious about explaining why they reject candidates to avoid illegal discrimination.

Reconnect with at least five mentors from your past:
  • Ask them the same questions you’re asking yourself now.
  • If they ask why you’re asking them, let them know you valued their previous insight.
  • Openly listen to them, but only act on what you know is true.

Create a fictional “personal mentor” to guide your career decisions:
  • Find at least three people who encapsulate different elements of what you want to be.
  • Write specific reasons why you wish to be like them.
  • Ascribe percentage values to each person to total 100%.

C. Connect the future and the past

Turn your general sketch into a life’s purpose, then work your way backward:
  • When you scope as far out as possible, there are only a few long-term career destinations:
    1. Working independently, where you choose most of your life decisions (e.g., entrepreneurship).
      • This requires plenty of hard work into specific skills and planning, but gives the most freedom.
    2. Senior worker, where you have tremendous technical authority over a domain.
      • This is never executive-level, but you’re getting paid to produce high-quality work you love.
    3. Manager, where you have social authority over other who do actual work.
      • While it’s much harder than the work itself (because it’s dealing with people), you may prefer the role and the power that comes with it.
  • Build a long-term plan for how you’ll encounter future life stages.
    1. What you’ll do if you get married and have children.
    2. The kind of work you’d do if you lost your ability to physically perform the roles of your current job.
    3. The plan for when you can no longer physically work (such as from aging or permanent disability).
  • Even if you don’t have your pre-retirement job planned, you should have a feeling about what sort of work you want to age into.

Consider your obstacles and possible challenges:
  • Additional training or education you’ll need
  • Any demographic limitations you may face (e.g., race, weight, height, learning disabilities)
  • Background experience that will haunt you (e.g., criminal history, nationality)
  • The kinds of people you may need to avoid or surround yourself with
  • The cultural expectations of the groups you desire to join

Imagine a standard workday of your desired job, then imagine the workdays that will lead to that day.

Track your current career path

A. List twenty-five milestones, relationships, people, jobs or experiences that brought you to now.

B. Create a visual map of the milestones.

C. Pick two random points and add five more milestones that brought you between them.

D. Create a fictional character with your milestones:
  1. Add ten bullet points anywhere on the map as plausible things you haven’t done.
  2. Write three fictional stories that can unite all the bullet points.
  3. Ask what type of characters those three people are.
    • What are their career ambitions and goals?
    • How did they get there?
    • How did this diverse set of milestones unite differently than yours?
  4. Write a future biography for each character.
  5. Reflect on the implications of these fictional characters with your own life.

E. Note your emotions throughout the map with a different pen color.

F. Review your map and figure out what you want to repeat, learn to avoid, or do differently:
  • Journal your feelings as you uncover your career pains.
  • Emotionally separate yourself from the worst portions of your job history.

D. Set immediate goals to attain your final purpose

Consider the skills and experience you can do now:
  • Make a list of at least 15 things you want to learn.
  • Imagine jobs that can fulfill the role of learning those 15 things.
  • Find relevant free or discounted online classes through SkillShare, Udemy, Alison, and Coursera.

Discover how to improve your marketability:
  • Make a website or put your portfolio online.
  • Find volunteering and internship opportunities.
  • Do whatever an employer could find attractive, but stay focused on your career.
  • A new job needs change, so you must be teachable.

Calculate the minimum income you need to maintain your lifestyle.

Commit time and energy to the task:
  • Prepare ahead by clarifying and focusing on your goals.
    • Devote 25 hours a week to the job change.
    • Set a specific date a few months later to reassess everything and measure your progress.
  • Expect doubt, frustration, and disappointment.
    • Generally, you will believe in yourself more than anyone else will.
    • Some part of any new position will be worse than your current one.

Zoom in on specific industries, then on specific jobs in that industry

Look for jobs that fit where your life is going:
  • If you want to succeed, try to find opportunities for personal development.
  • If you’re still young, look for chances to travel the “unbeaten path”.
  • If you have political aspirations at all, many companies may share your vision.
  • A more relaxing job gives time to recuperate from a severe hardship.
  • If you prefer the privacy and convenience, about 1/3 of the jobs can be 100% remote.

There are many reasons you may want a demoted title when transitioning between roles:
  • You want more pay
  • You need less stress or fewer responsibilities
  • You want to do something more meaningful
  • You don’t want to manage or babysit anyone
  • Companies or industries may have differing expectations for the same role

If you’re moving between industries, realistically analyze how you’ll transition:
  • To succeed, you must find something related to what you’re currently doing.
  • If you can’t find anything that meshes what you want and what you have, look for a job title that’s similar to your current one in a different industry.
    • e.g., If you’re a hardware technician but want to be a nurse’s aide, find a hardware technician role in the medical industry.

Most jobs either require 1 specific skill or a wide variety of smaller skills:
  • It’s not uncommon for people to think they need a wide variety of skills when they only need 1.
    • e.g., a great writer must simply compel the reader to keep reading, irrespective of other inner talents.
  • It’s relatively easy to know what to build on
  • By contrast, in variety-based demand, you can easily build out many “soft skills” (skills that apply to many things) that enhance your attractiveness to potential employers.
    • Very frequently, you can expand your soft skills slowly and steadily.
    • The advantage of soft skills is that they can feed into each other and develop exponential returns for your career across years.

Note current trends within your desired industry:
  • Consider the 5-year implications of current trends.
    • Generally, your work becomes obsolete proportionally to how specialized you are.
  • Make three estimates of the future situation: the worst-case, the best-case, and the most likely.
    • If you’re afraid of what may happen, shore up soft skills as a broad backup plan for anything that may arise.
  • Watch carefully for political trends that tweak the status of the role (e.g., unionization, government de-regulation).
    • If your job is slowly unionizing, you will be paid on existing in that job, not on your competence.
    • One consequence of a deregulated industry is that your pay will decrease for the same task, while entrepreneurial opportunities will increase.

While a 5-year plan is nice, it’s not necessary:
  • Excluding change-resistant industries like accounting, insurance, and law, most industries move around constantly from new technology and trends.
  • Play the situation by ear a little bit, since you’ll need to adapt to any changes that come your way.
    • Take smaller leaps before larger ones to avoid most of the risks from experience you couldn’t have planned for.
  • Sometimes, depending on how much you can pivot from your current employment situation to what you want, it’s better to only have a one-year goal.

When you have a decent intuition for the jobs that are most promising for you, it’s time to craft your image!

This page is Part 2 of Job Searching Made Easy. Part 1 was Preparing for the Search.