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How to pick the best career (FOR YOU)

Why so many of us are miserable working

One of the biggest disservices Corporate America and Hollywood ever did to working professionals is convince us we need to find meaning and fulfillment through our jobs.

Most jobs don’t offer that, and the few who do are either incredibly difficult to get, or they don’t pay enough. A job’s function is not to validate your existence, it’s to ensure the continuation and success of your employer.

50% of people don’t even like their jobs. This is a given because most of us work to make ends meet, not to have fun. Very few accountants find true meaning and fulfillment from spending all day on excel and pouring over numbers, but this is exactly what the employer needs them for.

I’d wager that a large portion of this disinterest comes from a mismatch of the expectations vs reality of the job’s pay, workload, and job stability. We’ll cover this in Section III.

The other reason people are so miserable is because they choose careers which don’t fit THEM. To pick a good career for you, you need to know yourself first. In Section II of the guide, we’ll cover how to understand your stress tolerance and skill floor, which will all impact the career you should pick.

In Section I, we’ll cover exactly what a job is and what it isn’t, and the true value behind any position you go with. This shift in thinking will help you evaluate opportunities for what they ARE, not what you WANT them to be.

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SECTION I: Function & Value

Society > Industry > Company > Function > VALUE

The foundation to this guide is the word “value,” which has become a nebulous term in recent years. When we focus on economics, value is what’s produced when a problem is solved. The more complex the problem solved, the more valuable its solution is.

The value of Netflix is in its ability to solve the problem of boredom at a mass scale, for example.

So long as a company has not gone out of business due to market competition, the company has value to whatever industry it’s in. Each industry is a pillar on the value of a society (GDP).

We measure a society’s value on the GDP of its industries. An industry’s value is measured by the gross output of the companies which make up that industry.

Your value as an employee (measured by your pay) is a measure of how well you’re able to provide value to a function for the company. Think of company functions as the activities which need to be completed to make sure the company is able to stay in business (meet gross output expectations).

The core functions of a business are:

  1. Revenue Generation: Sales & Marketing
  2. Product & Service Distribution: Supply Chain, Skilled Labor, Equipment/Inventory
  3. Administration: Finance, Management, HR

Thus, a sales manager provides value to the revenue generation function of the business.

Let’s be explicit about what a career IS and what a career IS NOT.

Work is the act of solving a problem. Your ability to solve problems is tied to your skills and experience. Some people attach emotional value to their work. This is fine, but not the primary focus of the employee-employer relationship.

job is a role in which you work for a company in return for payment which reflects the value of that work.

career is a series of jobs which are tied to 1-2 company functions, and which increase in value as your work skill improves.

Being a sales manager is Anthony’s job. Being a sales rep, then an account executive, a sales manager, a revenue operations director, and then a VP of Growth… is Anthony’s career.

Job titles tell employers the complexity of the problems you can solve for them are.

Generally, a job > no job, unless the only job available to you causes you serious mental and physical harm.

What a Salary/Wage actually represents

When trying to figure out which careers to go with, so many people are focused on how much they can make. This is missing the forest for the trees.

Your salary is a direct manifestation of the value your employer perceives you bring to the company. Let’s revisit our sales manager Anthony from before. Throughout his career, Anthony’s going to make this much (before commission):

Why did Anthony make $48K as a rep, and why does he now make $70K as a manager?

The difference is the value of the role– the complexity of the problems each job solves for the revenue generation function of the company.

  • As a Sales Rep, Anthony’s only job is to go to potential buyers and try to convince them to CONSIDER working with his company. It’s a hard job, but is straightforward.
  • As an Account Executive, Anthony’s job was to convince buyers to AGREE to work with his company. He has to sell the products/services, he has to communicate the value, he has to stay on top of the deal and make sure all stakeholders are happy. This is a more complex role, solving multiple problems, and so he brings more value to the company.
  • Now, as a Sales Manager, Anthony’s job is to keep tabs on the work the Sales Reps and Account Executives on his team are doing. He has to train them, help put out fires, create reports on their progress, manage their various personalities so everything runs smoothly, interview potential employees, evaluate what products to buy to make his team more efficient, and so much more. Because of the added complexity of the problems Anthony is solving, Anthony earns a higher salary.

With this in mind, when evaluating what career you want to enter, don’t just focus on salary. Look at what the job descriptions actually say. What work you’ll be expected to complete. What it’ll take to get promoted. How the expectations of the job impact your life.

You might say you want to be a doctor because you’ll make $230K/yr… but can you really be a doctor if you’re not willing to suffer through the lack of sleep, the burnout, the stress, or the inefficiency of the job?

Section II: Your Stress Tolerance & Skill Floor

A skill floor is the minimum skill required to do a job decently. A skill ceiling is the maximum skill you must have to reach the top 1% of a career. (These terms are adopted from esports)

For those of you who do want to reach the skill ceiling of your profession, it’s very easy to identify what you need. Simply determine the highest level title someone can reach, and work to build the skills needed to get that title.

For example, the highest level the average accountant can reach is Chief Financial Officer. You can read so many articles on what’s expected of CFOs, and there’s always dozens of job postings online addressing this as well. From there it’s working backwards to find which experiences you need to reach the CFO level.

I realized that many people aren’t interested in reaching the highest levels of their given profession. Most people just want a career that doesn’t make them miserable and pays them enough to live a dignified life. That’s why we’ll be focusing on identifying your skill floor and stress tolerance.

How to find your skill floor

You probably already know what you’re decent at and what you’re terrible at. You should do everything in your power to avoid picking a career that you can’t dedicate yourself to for 5 years at minimum. If you always struggled with math in school, you should stay away from careers where you deal with complex mathematical processes.

If you’re not good at articulating yourself, you’ll likely struggle in jobs which include a lot of presenting, negotiating, or managing people. On the other hand, someone who’s very artistically inclined and able to apply that work consistently should work hard to enter creative fields.

Most skills that don’t require you physically being somewhere can be improved by practicing online through Khan Academy or Youtube University. If you’re not sure where you stand on any given skillset, just find practice training opportunities online. 2-3 days of practice can give you a decent idea of what you’re good at and where you’re struggling.

Every job has different skill requirements, so it’s good to focus on developing Universal Skills. These are skills that will be used throughout your life, no matter the position. There are five:

  • Math
  • Written Communication
  • Spoken Communication
  • Creativity
  • Critical Thinking

I go into more detail on Universal Skills and all other hard/soft skills in this free ebook, but generally it’s best to rank any skill on a scale of 1-10, with 1 being terrible, 5 being average, and 10 being world-class.

Let’s say the average American struggles with math and at best can do basic algebra. That means that, in math, algebra will put you at the top of the bell curve for mathematical ability– right in the middle of the pack. Thus if you can understand and apply calculus and statistics, you should place yourself on the 7th point, nearer to the upper end of the population’s ability. If you can go deeper than that and understand topology, then you’re a very rare individual who should be ranked in the top 5% of society.

Jordan Peterson had a great lecture back in the day about Jobs and IQ. If you want to be the best in any given field, you need to be in the highest level of IQ for that field. The average person is not going to reach the highest levels of any field, and that’s okay. You just need to lean into your strengths.

Another way to find your skill floor is to answer this question: “What can your boss depend on you to do for them?”

For example, a business owner might be really good at sales, but he just can’t handle math. he hates anything that has to do with it. If you have the ability to do enough math to bring value to his business through a good grasp on the basics (bookkeeping), algebra (accounting) or statistics (data analysis), then he will pay you to do it for him. The skill floor is the minimum skill level you can meet to justify getting paid.

With that in mind, you don’t want to enter a job where the skill floor is higher than you can meet. This is where you’re going to start dealing with stress and become miserable.

What happens when you stay in a job that destroys your self confidence?

When you can’t meet the skill floor of a position, you’ll know it. Repeated failure to meet expectations will destroy your self confidence and your long-term career success.

Imposter syndrome is something everyone feels at some point, but the longer you’re in a job that just doesn’t fit you, the more obvious and constant the feeling is going to become. The last thing you want as a professional is to lose your confidence. That lack of confidence is going to drag itself into your work and make you less efficient, less effective, and less valuable as an employee. Here’s what that’ll look like:

  1. Minimizing language: You can’t communicate assertively and your contributions to the company suffer. You use maybe, kind of, sort of to avoid using yes and no.
  2. Perfectionism: While you should always do your best to be great at your job, insecure employees tend to drift into perfectionism. Why? She wants to avoid risk, mistakes, and criticism. She worries that if others see her work, they’ll know she’s not right for the job and fire her. Perfectionism blinds you to the fact that you were hired because you demonstrated reasonable ability for the job. You become defensive about constructive feedback, which leads to…
  3. Stagnation: Because you’re worried you won’t say the right thing, you say nothing at all. You let others take the lead and contribute little to conversations. Your self doubt is evident to everyone, and so you become invisible. Invisible workers don’t get raises and don’t get recognition. This only compounds the imposter syndrome you’re already experiencing.

Employees without self confidence advocate for themselves less and take on less challenging work, leading to less recognition and less money down the line.

This leads to more stress, since now your own sense of self is being attacked by your job!

How much stress can you handle?

Just as important as understanding what you can do is understanding what you can’t. Half of this is determined by stress tolerance, and the other half is effected by your life goals.

Many people who choose law as their profession do so because they’re intelligent and want to make a lot of money. Once they’re actually in the job, though, they can’t handle the stress that comes with it. They struggle to keep tabs on so many different laws, they grow depressed about clients who end up in jail, and they can’t handle the highly-regulated environment of the US Legal System. Is it a wonder 11.5% of lawyers are suicidal and 20% of them drink?

You shouldn’t avoid stress, as it’s the best way to learn and grow, but be weary of jobs that put so much stress on its people that they regularly have panic attacks and can’t sleep.

To assess your stress tolerance, you should keep watch of warning signs that your job isn’t right for you. Recognize common stressors in your life and how you respond to the physically and emotionally. Think of irritability, muscle tension, headaches, etc.

What are your coping strategies for stress? Many alcoholics start drinking to “relax” after dealing with a difficult day at work. Some people shut down and play video games or watch TV. Others go for runs or weight lift to get their endorphins up and counteract heightened cortisol levels.

Next, you should note if you have a support system, and how often you have to depend on that support system to handle stress. It’s normal to let out some steam about work or talk about your fears to your spouse, but constantly turning to them and putting responsibility for your mental health on them is a strategy which doesn’t allow you to grow… and it will put a lot of strain on your relationship.

If you get stressed quickly, use negative coping strategies, and push your stress onto friends and family, you should avoid careers which are notorious for putting pressure on workers. No law, no sales, no healthcare, etc. Stick with something more relaxed.

Alternatively, you can improve your stress tolerance by using these stress management techniques.

How life goals impact your career

The only people who are justified in living to work are those with the life goal of climbing the corporate ladder. Executives dedicate a lot of mental energy and time to their businesses, and this paradigm is a necessity if you want to reach the upper echelons of the business world. (This is partly why CEOs are paid so much– they’re willing to give their lives to the company)

If you’re not aiming for the C-Suite, though, work is not your life, and work will never give you meaning.

You work to live, not the other way around.

So what do you want to do with your life? Do you want to travel, make art and music, build things, become a community leader, start a family, etc?

  • Example 1: Primary caregivers of children and adults, who are typically women, should prioritize remote work. Everyone benefits from working remote in my book, but since the gender pay gap is really a motherhood penalty, it’s worth highlighting.
  • Example 2: If you’re really passionate about video games and want to make your own game one day, you should look towards the programming field and get a position where you can build skills that can translate into game development.

Your career doesn’t have to mold itself around your life goals (a plumber can still be a Youtuber on the side), but if you want to quickly develop your skills, it’s very useful to do so.

Section III: Expectations vs Reality

Pay doesn’t correlate to workload

In blue collar fields, your pay tends to be directly connected to the amount of the work you’re completing and how many hours you put in to solve problems. We see this in how tradespeople take complete advantage of overtime pay– they want to put more time in to get more money back. This is the benefit of hourly pay.

White collar workers, on the other hand, deal with a different struggle. Workers can blast through assignments in a few hours and find that they have to twiddle their thumbs until 5pm to go home. Alternatively, white collar professionals can face more and more work being piled on their desk at 4:30pm, but they don’t get paid extra for staying up until 10pm to finish it.

This is the consequence of salary pay: you have to stay in the office for 40 hours even when you have nothing to do, and you can be made to work more than 40 hours without extra pay.

New accountants are often shocked at the amount of hours Big 4 Firms require them to put in for $60,000/year after graduating university. The complexity of the problems junior accountants are solving are low, and so they’re paid low. Not as low as a retail worker since they did have to get a degree to meet the skill floor, but low in comparison to accountants with more experience.

What this means for you: Be very, very careful about your pay expectations when you’re entering a field. Don’t bother with the national average pay for the field, focus on your state. If you can get data on your town or city, prioritize that. You don’t want the nasty surprise of being offered $20,000 LESS than you thought you were qualified for.

Payscale is the 2nd best resource I’ve used to find high quality stats. Its UX design is more convenient than the #1 source, the US Bureau of Labor Statistics.

Why you need 3-5 years of experience for an entry level job

Very few Americans expect any loyalty from their employers. Employers have built a reputation of treating employees like “cogs in the machine,” chewing people up and spitting them out when convenient. Layoffs are quick and brutal, and older workers expect to be pushed out before their time to make room for new blood.

This is just business on the part of employers. It’s perfectly logical for them to prioritize their stockholders and leadership above their lower-level staff. In part, the international market forces businesses to show no loyalty to their employees so they can stay competitive.

However, Americans fume when companies turn around and expect loyalty from them anyway. There’s no trust on the employee’s side that they won’t get canned when it’s convenient for the company, so why should they be loyal?

The modern American worker is a mercenary. Gone are the days of the “company man.”

Because neither side offers loyalty, we’ve found ourselves at an impasse. Why should a company take time and resources to train you, when you can leave at any time and take those skills to a competitor? Game theory suggests it’s better to just let someone else do it.

But when NOBODY is training, and employers refuse to lower their experience expectations, workers are left with the short end of the stick. Either they make their own experience through freelancing or they work for free to get experience (internships, volunteering). Neither pays their bills.

In this new mercenary-like job market, you should ask yourself how you’re going to get experience in your field. Outside of the typical college program, you can:

  • Become an intern or apprentice: These opportunities provide hands-on experience and training in a professional setting. Small businesses are more likely to be swayed by candidates who demonstrate enthusiasm and a willingness to learn
  • Volunteer: Offer your time and skills to nonprofit organizations, community groups, or small businesses in your area. Volunteering can provide valuable experience, allowing you to develop transferable skills, build a professional network, and gain references for future job applications.
  • Freelance: Building a portfolio of work can demonstrate your skills and capabilities to potential employers, even if you don’t have formal experience. Platforms like Upwork, Freelancer, or Fiverr can connect you with clients.
  • Online Courses and Certifications: Take advantage of online learning platforms such as Coursera, Udemy, or LinkedIn Learning to acquire relevant skills and certifications in your desired field. The vast majority of these will NOT get you a job on their own, so I highly recommend you apply what you learn to an internship, volunteering position, or freelancing.

The good thing about this mercenary-like job market is that it gives you more opportunities to push yourself and figure out where your actual limits and wants are, rather than box you in to one role for 20-30 years.

Final Thoughts

What have we learned today?

  • Your value as a worker is directly tied to the value of the problems you solve for a company functions.
  • The smartest people (those able to reach the highest skill levels) are the ones who excel in any given field, and thus get paid the most.
  • Those who want less stress and more time outside of their job to live their lives get paid less since they’re providing less value to the company than those who can handle more stress and longer hours.

With this in mind, you should be able to look at any given career and know if it’s right for you. Of course, nothing beats actual experience in a field, but we can’t try to be everything. There’s not enough time and most of us have bills to pay!

And a quick reminder: I created an ebook that covers Universal Skills and all other hard/soft skills you’ll face in the job market. Get your free copy here.



If you found this guide useful, let me know in the comments. My goal is to make this Atlas a place that you can come back to for financial help that isn’t just a regurgitation of everything else on the internet.

You can learn about the secrets of wealth in America on the Youtube Channel  as well.

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