Ask Yourself These 8 Questions To Find Your Next Career Opportunity

There’s a lot of material about how to get a job and how to advance your career, but not a lot about what career path to pursue, or whether you should start a business instead of getting a job. There’s a lot of material about how to start a successful business, but not a lot about what kind of business to pursue.

It’s always nice to win, but there’s nothing worse than winning a game that you shouldn’t have been playing. If the game won’t help you achieve your goals, or if the game has odds that are stacked against you, then it doesn’t matter how hard you work or what techniques you use to get ahead. Naval Ravikant, CEO of AngelList, said “…hard work doesn’t matter that much…what you do, and how you do it, is so much more important than how hard you do it.”

If you don’t consciously choose what game you want to play, you can easily end up playing the wrong game. Often this entails taking the path of least resistance and playing a game that everyone else plays. Playing everyone else’s game can get you the results that everyone else gets. If you want greater or different results, you need to choose your game wisely.

If you only focus on winning the game that you are playing, you can only win what that game allows you to win. If an entrepreneur doesn’t take time to consider what market to be in, the company can only grow as large as that market. In his book, Finite and Infinite Games, James Carse writes: “Finite players play within boundaries, infinite players play with boundaries.”

There are so many opportunities in the world. Which ones should you pursue? First, you need to know what your values are and what you’re trying to achieve. If you don’t know what you’re trying to achieve – don’t worry – there are games that can help you achieve multiple outcomes. Then, you can evaluate the game based on it’s ability for you to achieve your goals. 

This article covers eight techniques for evaluating career opportunities based on lessons from Warren Buffett, Charlie Munger, Naval Ravikant, and Nassim Taleb.

1. What are the costs of validating the game?

Not all games can help you achieve your goals. Even if your goal is simply to enjoy the game, you need to get information to confirm that you enjoy the game.

Find evidence that the game can achieve results for anyone, and that you can achieve results by playing the game before taking more risk than you can afford. It will cost time and money to validate that a game can achieve your goals. Make sure you don’t waste it. 

Validating some games requires more time and money than other games. It takes at least four years and about a quarter of a million dollars to get an undergraduate degree. Most people are confident that they want a job that will require a college degree. You might not know which job you want, but a degree from a good school will help you get into a variety of jobs even if your major doesn’t perfectly match.

It can take years and millions of dollars in funding to know if a startup idea has significant potential. That’s why venture capitalists often fund them in stages: a few hundred thousand dollars to see if it can get off the ground, a few million dollars to see if they can get some initial traction, and so on.

In other games, however, there are ways to get more information with even less investment. Coffee meetings, internships, side projects, books, blog posts, consulting projects, etc.

Look for games where the cost to validate is low, all else equal. Once you have enough information to be confident in your investment, pursue it aggressively.

2. Do you enjoy playing the game?

Finding work that you enjoy can be a shortcut to achieving your desires outcomes – or “ends goals.” Most people work so that they can make money – the “means goal” – so that they don’t have to work anymore or so that they can spend it on something they want – the ends goal.

If you can find a game that you enjoy, you can skip a step, or at least, shorten it.

If you love to surf, you could teach surfing. If you want to help people, you could become a social worker. If you hate waking up early, you could work a job that starts late or has a flexible schedule.

If you enjoy the work that you do, you might end up more successful. You’ll be more energized and motivated each day. If you hate the work that you do, you’ll eventually burn out. However, most of the work that people enjoy doing doesn’t pay well. Travel blogging is fun, but most people don’t make banker money from doing it. Other people gain a sense of meaning from being challenged by work, or from what the pay enables them to do. Money brings you freedom, the ability to provide for your family, a big house, etc.

Find your balance between an enjoyable process and a lucrative outcome. If you’re fortunate enough to enjoy lucrative work, congratulations. Otherwise, find your balance between outcomes and process. If you get offered millions to do something you hate, you’ll probably do it, at least for a short period of time. If you enjoy the work that you do, you’ve gained benefits that would otherwise only be available after years of playing a different game.

3. Will the game achieve your goals?

I like to read books about psychology and philosophy, but it doesn’t directly help me achieve my financial goals. I gain some skills that I can use at work, and it gives me fodder for writing. If I evaluate reading purely based on its ability to help me achieve short-term financial goals, then reading is not a good game for me to play.

I do believe reading is important and valuable for a number of reasons, but achieving short-term financial goals is simply not one of them. I’m also not saying that the only thing that matters is your short-term financial goals. I do believe that reading will help with my longer-term goals. I also enjoy doing it.

Prioritize your short and long-term goals and choose a game that can help you achieve them. You’re probably not going to become a billionaire as a surfing instructor. You’re also probably not going to have time to spend months at a time traveling the world if you’re running a venture funded startup. Accept the tradeoffs associated with the game that you choose.

4. What’s the risk and reward?

Venture capitalists lose on a large percentage of the investments that they make. However, when they do win, they win big, and the big wins more than make up for the losses. The risk is high, but so are the rewards.

Risk is not necessarily a bad thing. In some cases, people will be scared by risk, which means less competition and more potential reward for those who are willing to take the risk. Risk tolerance is a personal decision.

Some people prefer to take more risk when they’re younger and have fewer obligations. You’d rather succeed than fail at starting a company, but even if you fail, you gain skills and experience that will help you in your next game.

Most games, however, don’t have binary outcomes. You can win a little by gaining skills, earning money, or making connections. You can lose a little time or money, but you probably won’t win a lot or lose a lot. Most salaried jobs are a good example of this.

Every potential outcome has a probability of coming to fruition. If you’re going to play a game with a low probability of success, look for one with significant rewards if you do succeed.

Nassim Taleb suggests taking risks that offer the potential for significant profits, but avoiding the risk of ruin. “Small injuries will be beneficial, never larger ones” he says. Taleb cites Warren Buffett to make his case: “In order to succeed, you must first survive.”

To measure the risk and reward of a game, evaluate the probabilities of anyone achieving a set of possible outcomes. Then, consider the potential rewards of each outcome. Factor in any competitive advantage (see below) or competitive disadvantage that you may have, and compare it to your personal tolerance for risk.

5. Do you have a competitive advantage?

A competitive advantage is a factor that enables you to outperform the competition. Having a competitive advantage can increase your chances of winning, increase the benefits of winning, or reduce the costs of losing.  

Farnam Street provides a helpful diagram that illustrates the importance of focusing on opportunities that play to your strengths:

You can get yourself into “trouble” by playing a game that you think you know, but really don’t. Fortunately, as “what you know” grows, “what you think you know” shrinks.

The Farnam Street article includes a quote from Charlie Munger about the importance of having a competitive advantage:

You have to figure out what your own aptitudes are. If you play games where other people have the aptitudes and you don’t, you’re going to lose. And that’s as close to certain as any prediction that you can make. You have to figure out where you’ve got an edge. And you’ve got to play within your own circle of competence.”

In the 1996 Berkshire Hathaway Letter to Shareholders, Warren Buffett writes that it’s not very important to increase your circle of competence, but it’s critical to be aware of it.

What an investor needs is the ability to correctly evaluate selected businesses. Note that word ‘selected’: You don’t have to be an expert on every company, or even many. You only have to be able to evaluate companies within your circle of competence. The size of that circle is not very important; knowing its boundaries, however, is vital.”

Many pundits criticized Buffett and Munger for not investing in bitcoin and successful technology companies such as Amazon. I believe that Buffett and Munger didn’t need to make those investment because they have a strategy that works for them.

Some games don’t require a competitive advantage. Those are good games to play. In the 2007 Shareholder’s Letter, Buffett writes: “if a business requires a superstar to produce great results, the business itself cannot be deemed great.” In other words, if you can win a game without having a significant competitive advantage, the odds are on your side.  

Friends of mine have run agencies that provide services to businesses. They discover that in order for the agency to be profitable, they’ll need to keep working at 100% of their capacity for the foreseeable future. Clients want to work with them. Without their competitive advantage in terms of network, skills, experience, and work ethic, it’s hard to keep the business running.

In contrast, there are many fields where there is either large enough demand for people or small enough supply of people that you need not be the world’s best in order to succeed. Accounting and SEO come to mind as good examples here.

Skills and knowledge can provide a meaningful competitive advantage. Your assets can provide a competitive advantage, too. if you have a lot of money, or if your expenses are low, you can afford to be patient with your investments. If you have a lot of time, you could spend it working to make money.

Look for a game where you have a competitive advantage, or look for a game that’s good enough that you don’t need to be the world’s best in order to win.

6. What are the benefits?

Naval Ravikant says that “you will get rich by giving society what it wants but does not yet know how to get.” In economic terms this means playing games with high demand and limited supply. When there are more people willing to pay for a service than there are people willing to provide it, the price goes up. That generally means higher prices and the potential for profits.

Search engine optimization (SEO) exemplifies a field with favorable supply and demand dynamics. Many businesses want to get customers for free through Google. Doing so requires technical expertise and difficult work. Most people don’t want to learn how to do SEO, let alone actually do it. Many marketers would rather focus on social media because it’s way more fun. If you’re able to sacrifice the fun, or if you happen to enjoy the technical aspects of SEO, you’ve found something that many people need but don’t know how to get. You can provide something that’s in high demand with limited supply for a high price.

Travel blogging, on the other hand, has less favorable supply and demand dynamics. A lot of people would love to become a professional travel blogger. This means a large supply of travel bloggers exists. But is there enough demand for travel blogs for all of them to achieve significant rewards? In order to succeed you would need to be one of the best travel blogger in the world – a Leonardo Di Vinci of Instagram.

It’s also important to factor in how long it will take you to realize returns. The Time Value of Money is a financial concept that says that a dollar that’s available today is worth more than a dollar that will be available tomorrow. This is because you can earn returns on the money that you have now, but not on the money that you don’t have now.

Bitcoin doesn’t pay dividends to its owners. Owners of bitcoin only receive money when they sell it. The price could also decline for extended periods of time. You might have to wait a decade to fully realize the returns from an investment in Bitcoin. You might never realize a return if Bitcoin fails.

It’s important to consider what obligations you have and what other opportunities you may need to forgo if you’ll need to wait a long time to realize returns from an a game. When do you want to retire? Do you need capital to make other attractive investments or cover expenses?

In some cases it might not be possible to reap the rewards of a game that takes too long to deliver returns. “No person can get the returns of the market unless he has infinite pockets and no uncle points,” Taleb writes. It can take years to sell a large enterprise software contract to a big company. If you can’t afford to wait that long to earn the revenue, it might not be the game for you. On the bright side, being patient and tolerating ups and downs can provide massive rewards. Selling large enterprise software deals to big companies can be a very profitable business. Buffett stresses the importance of patience in investing by saying “the stock market is a device for transferring money from the impatient to the patient.”

Some games continue to provide returns even after you stop playing them. If you work at a company that doesn’t provide stock options or retirement packages as part of the compensation, once you stop working there, you stop making money. When you start or work at a company and get stock options, your returns grow as the company continues to grow, even if you no longer work there.

Most software products can serve new customers without any additional cost. Once you create a software product, you can continue to profit from it. Same with ebooks. Once published, it costs almost nothing to sell additional copies to readers. A masseuse makes money in direct proportion to the time spent massaging clients, and can serve only a small number of clients per day. The author of a book on massage therapy makes money in proportion to book sales, which do not have a daily limit or require time or money to produce. That means you get paid while you sleep, play other games, or do whatever else you want to do with your time.

Buffett and Munger love businesses with a low cost of selling additional units. “The ideal business is one that takes no capital, and yet grows,” Buffett said. “Return on Invested Capital” – net income as a percentage of capital required to run the business – is ratio they use to measure this.

Look for games with significant upside potential. Compounding returns, such as equity in a company, and recurring returns, such as book royalties, are a plus. The lower the cost to achieve those returns, the better.

7. What are the costs?

Benefits are great, but you must also count the costs. Costs come in many forms. The most common are financial costs and time costs. People often forget opportunity costs. That is, what you forgo when you choose one opportunity over another.

When you say “yes” to one game, you simultaneously say “no” to another game. A minute spent watching TV is a minute that can’t be spent reading. Most people think about the costs and benefits of the game they’re playing, but they ignore or neglect costs and benefits of other games that they could otherwise play.

Some games have greater opportunity costs than others. If you work in investment banking, you’ll work about 90 hours per week. That will leave you with little time and energy to pursue other games, or even hang out with friends.

If your job runs from nine to five, isn’t too tiring, doesn’t require a long commute, and offers ample paid time off, you’ll have plenty of time to play other games. Such a job has low opportunity costs.

Having margin in your schedule also enables you to pursue new opportunities as you discover them. I was fortunate to have had enough slack in my schedule to be able to spend time following the bitcoin markets in 2017. The investments that I made then paid off.

Should you keep your options open or focus? Like all advice you read on the Internet, it depends. It’s a good thing Jeff Bezos focused on Amazon. That investment worked out well for him. However, if you don’t know what will achieve your goals yet, explore or do something that can give you opportunity in the future.  

Diversification is a common portfolio management strategy for reducing risk. When you are diversified, you don’t have all of your eggs in one basket. If you lose one game, you aren’t hurt as much. You also increase your chances of finding a game that you can win.

According to Naval Ravikant, it’s critical to have time to search for opportunities:

It’s better to treat a lot of your time as a search function, where you’re searching through the set of jobs, you’re searching through the set of dates and spouses. You’re searching through the set of hobbies until you find something things you love. When you find things and people that you love, you go all-in on them.”

Warren Buffett emphasizes the importance of doubling down once you find something that works:

Opportunities come infrequently. When it rains gold, put out the bucket, not the thimble.”

If you haven’t found a pitch that you want to take a big swing at, take small swings at a few pitches. Find ways to keep growing while you explore. Consulting is a good game if you want the ability to diversify. You can work one or two clients, gain strong professional experience, make about as much as you would at a full-time job, but only spend half as much time working. That gives you time and money to pursue other opportunities.  

8. What are the second order effects?

Almost everyone plays more than one game over the course of their lifetime: the education game, the work game, the family game, and so on. Don’t just think about a game in terms of its immediate costs and benefits. Think of the second order effects.

Some games offer more than one way to win. They present opportunities for you to win other games in the future. You can make money, have fun, gain marketable experience, improve your skills, and make connections all at once.

Blogging is a game with more than one way to win. I started my blog as a side project with the goal of building my personal brand and expanding my network. I accomplished those, and I also learned a lot about content marketing, and I built a large audience. After seeing what I had achieved, people started offering me money to do the same for their businesses. I’ve now spent the past six years doing marketing for venture funded startups and Fortune 500 companies. I’ve also grown my blog into a profitable business that runs almost entirely on auto-pilot. I’ve opened multiple doors and achieved multiple goals by playing one game.

If you don’t have a lot of confidence in what game you want to play, play a game with more than one way to win. Even if you feel certain about the game that you are playing right now, remember that things change. Play games that can help you win future games.

What do you want to do with your life?

Most people focus on how to win a game before deciding what game to play. As a result, they end up playing a game that, even if they win, will not help them achieve what they truly value. I ask myself the following questions before choosing what games to play:

  1. What do I want to achieve?
  2. Can this game achieve those goals?
  3. Should I play this game?
  4. What are the second order effects of playing this game?

Keep in mind that you don’t need to have all the answers about what to do with your life, or even what you should do right now. Make progress every day, keep gathering information, and give yourself multiple ways to win. If you have enough money to live the life you want, you don’t have to start playing a game that you don’t want to play. You can wait until you find a game that you do want to play.

When you commit to a game, commit fully. If you need to pivot later, pivot later. But once you’ve found a game you want to play, play hard. Accept your game for what it is. You can have your drinking buddies, and your lifting buddies. You don’t talk about lifting with your drinking buddies and you don’t talk about drinking with your lifting buddies. Similarly, you can have your financial game and your fun game. Your financial game isn’t fun, your fun game doesn’t help you financially, and that’s fine.

Accept the tradeoffs. Remind yourself of your values and the benefits of the game that you chose. You made a choice. You knew there would be challenges and costs. You expected receiving some benefits, and you accepted foregoing others.

You can also play more than one game at a time. I’m currently playing the job game, the blog game, the moving to a different city to improve my quality of life game, and a couple others, too. Life is good now and I’m set up for it to keep getting better.

Most importantly, be intentional about choosing your game(s). Choosing the right game will help you avoid dead ends and keep you motivated because you’ll have a strong chance to win and you’ll be working towards benefits that you actually value.