Playbook Part 2 - Career Path

There’s no getting around the fact that you’ll need to earn significantly more than you spend in order to eventually be financially sustainable. For many people, this means finding your way into a higher paying career. This section will outline how to select a new career and set yourself up for success in getting the credentials you need to begin working in it.

Selecting a Field of Work

Identifying your potential options for a career and then understanding what you can expect from them will take some investigation. And it’s completely essential. In order to identify potential types of work that will help you achieve financial success, evaluate your options against these criteria:

It is In Demand and Well Paid - When a job is in demand it means that lots of people are being hired into that field. That helps ensure when you’re ready to enter the field, you’ll have plenty of job opportunities. It also tends to mean that there’s a lot of jobs available relative to the number of people qualified to do the work, which often can help keep compensation higher, although that's not necessarily the case. You’ll want to limit your search to those fields that offer both good starting and good mid-career salaries. It’s hard to define exactly how much income you should target, but achieving at least the median level of income for your local area within the first few years of employment is a pretty good benchmark. In addition to having lots of jobs available right now, you also want to select a field that is growing in demand, to help ensure that you’ll have longevity in your career without having to change course again too soon.

There is a Path to Advancement - Make sure your chosen field has a viable path to ongoing advancement. This could take any number of different forms. In some types of work you simply build seniority and your compensation increases. In some you need to ‘climb the ladder’ and seek out promotions. In others you’ll need to continue to get ongoing training and education in order to advance. In any case, investigate past the entry level roles and make sure there’s a true and fairly well defined path to advancement that comes with increased compensation.

It is a Good Value of Investment - You’ll almost certainly need to invest something to get yourself prepared for your new career. Most likely it will take time and money, such as going through and paying for a training or educational program. It is critically important that the financial benefits of getting a job in your new field merit the costs to get there. To simplify, you’ll want to prioritize the career options that give you the best compensation for the least amount of time and money invested. For example, don’t spend the money and time on a 4 year degree if the career prospects at the end are no better than what you could get with a 2 year degree or even less. Only go after the 4 year or more advanced degree if the career prospects for that specific degree warrant it. In some fields, like many trades, you earn money as an apprentice while you’re in training, which in the right circumstances might offer a very attractive value compared to spending time and money on schooling with no compensation. Many types of skills certification courses and trade schools or boot camps offer other paths into careers. There’s certainly not just one right answer here, but a vital consideration is making sure the costs and benefits of getting into your new field add up to a good value compared to your other options.

You won't hate the work and could be good at it - There’s a bit of a debate about the wisdom of the advice to find work that you love. We don’t have to solve that debate now, but it is worth pointing out that no matter how much you love it, and even how good at it you become, many many jobs will never let you advance out of a financially precarious position. If the field you love happens to also meet the rest of the criteria here (in demand, good advancement, good value) then good for you. Go for it! If not though, or if you just aren’t clear on what you might love doing, a more useful place to start might be to do work that you won’t hate. It sounds at first like settling for a consolation prize, but that’s not entirely true. First off, it lets you keep the things you really love to do as hobbies and not try to squeeze a living out of them, which can be a shortcut to not loving them anymore. Also, there’s some evidence that working hard at something develops the passion for it. So as long as you’re not getting into a field that you know you’ll hate, there’s a good chance your love for it will materialize along the way. In addition to not hating your work, it’s best to pick among the things you think you could become good at, the ones that leverage your strengths. That will help ensure you’re successful with it, which gives you that much more opportunity to enjoy it.

Planning for Success in (Re)Training

For this part we'll assume you've found some kind of educational or training program (although this is certainly not the only path!) and you are planning how to make it work . When it comes to investing in training or education to jump start a new career there are two, potentially catastrophic pitfalls that need to be avoided. One is investing a significant amount of time and money and not completing the course of study and therefore not being a candidate for a new job. The second is completing the course of study only to find out at the end that it didn’t prepare you to be a strong candidate for a prosperous job. Either of those two cases can leave you in worse financial shape than if you had done nothing, because you’ve made the investment in time and money and have little chance of getting a return. The time to avoid those pitfalls is right at the very beginning. Here’s how:

Identify and narrow down your options for getting the skills and credentials you need - There’s almost always more than one way to get what you need in order to be ready to start a new career. If one doesn’t immediately stand out as best for you, keep investigating and note the pros and cons of each option until you can choose a path.

Write your ‘to do’ list and put it on a timeline - Lay out all the steps, either week by week or month by month, that get you from today until you start your training program. What do you need to do before you apply? Save up some money? Finish other work / projects? Are there prerequisites? What's their schedule? When can you apply? When will you find out if you are admitted? When does it start? You don’t need to include lots of detail on each step, but you do want to be certain that all the steps can fall into place in time to keep you on track.

Ask and answer all the right questions - To make sure you have a clear path to success, you need to ask yourself challenging questions about how things will work and what could go wrong all the way through from now until you’re in your first job in your new field. Imagine you have to convince somebody else that you’re going to be successful. What questions might they ask you, and do you have good answers? Below are some examples as a minimum starting point. You should add to this list though. What could go wrong? What makes you nervous about your plan?

How will you manage adding the educational program to the rest of your life? Are you planning on working? How many hours? How much time will your training require? Will you have enough time for everything? Have you demonstrated good time management in the past? Are you getting financial aid? How much does the training cost? Will there be enough money to get you through?
Why do you believe you’ll successfully complete the program? What is the graduation rate? Are you more similar to the people who succeed or those who fail? What resources exist to help you if you struggle to keep up? What’s your track record with similar types of education / training?
Why are you confident someone will hire you when you start applying for jobs? Is the degree or certificate that you get at the end recognized and valued by employers? What’s the placement rate of graduates into the kind of job you want to get? How many job listings are posted like the ones you’ll apply for when you’re ready? What’s the average starting salary? How long after graduation does it take people to get hired? Who are the major employers? Have you talked with anyone who’s gone through this program and been hired successfully? Does the school / program help connect you with people in the field and / or with open positions. How much networking and applying for jobs do you have to do on your own?

NOTE: Schools will often have resources to help you plan and answer many of these questions. It may be a bit of a red flag if they can’t help you build confidence in your eventual success. Remember too, it is their job to convince you that their program is a good value for you. Approach their information with a healthy dose of skepticism and verify facts another way when you can.

Once you’ve gone through these planning steps, you should have confidence that you know what to expect between now and completing your program, that you will in fact complete it successfully, and that once you have, you’ll be well prepared to start your new career.

Considering Debt

While not universal, it is very common to need to borrow money in order to get through education or training programs.The cost of tuition combined with often having fewer hours available to work can make it impossible to succeed without taking on substantial debt. While this can feel scary and you need to be smart and cautious in how you use debt, it is not something to be feared in the right context. Probably the best use of debt is to purchase something, like education, that will return more economic value than the debt will cost you. Rather than focusing on the total amount you’ll need to borrow, think instead about your cash flow (the money you’ll earn and the money you’ll spend on debt payments) once you’ve started the job you expect to get. For example, if you’ll need to pay $500 per month for 10 years to pay off your debt, but you’re expecting to increase your salary by $2,500 per month in the first year of your new job (plus growth potential) then borrowing the money is probably still a great investment. (Note: don’t be fooled by loans that have low monthly payment options if the payments aren’t enough to fully repay the debt in a reasonable amount of time, like 10 years or less. Compare your expected salary increase to the amount you need to pay in order to pay off the loans on time). The other consideration to determine if borrowing money is a good value is to ask yourself how sure you are that you’ll finish the program and get the job and salary you’re expecting. If you don’t have a high level of confidence, borrowing money is probably not a smart risk to take. If you do decide to take out loans to invest in your future career potential, be smart about how you do it. Only borrow as much as you reasonably need to and investigate to find the lowest interest rate that you can.

If, after all this consideration, you just don’t think taking out loans is a good idea, there are some options for career advancement that require little to no debt. These might be worth your time investigating. For example many trades have apprenticeship programs that let you work and earn money while you’re acquiring skills. Similarly, some entry-level jobs come with educational benefits that can set you on a path to career advancement. Military service is also a path that can lead to career training without taking on debt. While not very common, it is also worth investigating if there are grants and scholarships that could help you.

Getting Your First Job in Your New Field

Once you’re on track getting your education or skills for your new career, it’s time to start laying the groundwork to become a competitive applicant for the job you have your eyes on. Don’t wait until you’re wrapping up your program of study to start this work. It can easily take 6 months for these efforts to have the time they need to bake, so it’s best to get started as soon as you’re within 6 months of applying for jobs. Some programs of study, in addition to giving you the skills you need, also do a pretty good job of setting you up to step right into your first job. Don’t take that for granted though. Find out (if you don’t already know) how much your program helps with this part and plan on filling in the gaps yourself. Your success is your responsibility.

When approaching this work, the key perspective to keep in mind is that applying for jobs is a competitive endeavor. It’s possible that there will be plenty of jobs to go around, but it’s pretty likely that the best of those jobs will go to the best of the candidates. Following are the key areas you’ll use to differentiate yourself and be a competitive applicant.

Hard skills and credentials - This is pretty straightforward. You need to have the skills required to do the job. It’s worthwhile going through several job listings for the kinds of jobs you’re going to want to apply for and making a list of the most common skills requirements. Then make sure you’re on track to be able to demonstrate those skills by the time you’re ready to apply. Also, think about how you’re going to differentiate yourself from everyone else working toward the same jobs. Will you have more skills? Better skills? Along the same lines, many jobs require you to show some specific credentials, like a degree, certificate, license, etc. Make sure too you understand what’s required of you to get those credentials and that you’re on track to have what you need.

Experience - One of the best ways to convince a potential employer that you can do the work they need is by showing them that you’ve already done it. Even for entry level jobs, showing you have some experience gives you an advantage. Of course, getting experience before you’re working in the field presents a bit of a challenge. So get creative and put in some extra effort. Remember, even if your program of study gives you opportunities to gain experience, your goal is to differentiate yourself. Having more experience or more varied experience than your classmates is one way to do that.

Soft Skills - Soft skills can be effective differentiators as you compete for jobs. An essential part of applying for jobs will be understanding which soft skills are most important, cultivating them, and knowing how and when to demonstrate them. Saying that you have a soft skill doesn’t carry nearly as much weight as actually putting it on display.

Connections - Knowing people within an industry, or even better within an organization where you want to work, can be huge for making you stand out when you’re applying for jobs. In fact it can make such a significant difference when you’re job hunting that a great goal would be to have a good relationship with someone inside every organization where you’re applying. It would seem that having inside connections is just a matter of luck, but in fact these connections can be created and cultivated with a bit of focused effort. This will take time. Plan to start growing and strengthening your professional network, and specifically contacts within organizations where you’d eventually like to work, at least 6 months before you plan to apply for jobs.

Action - The final step to capitalize on all your preparation and get yourself started in your new field is to go through all the basic mechanics of applying for a job. Polish up your resume. Apply for jobs (ideally where you already have professional contacts). Prepare for your interviews (including planning how to show off your soft skills). The actual work of job hunting can be daunting. Even with all the best preparation on your side, some of your applications will likely get rejected. Don’t let any of that slow you down. It might be useful to set a goal, like to apply to 10 jobs that you want. Stay heads down working on it until you hit your goal. If after your 10 applications you’re not getting any interest, it might be a good time to take stock, reassess your approach and maybe ask for help seeing what about the process you might be missing. Until then though, don’t let any doubt about your eventual success slow you down. You are the solution to an employer's problem. You just need to connect with the right one.

With your hard skills, experience, soft skills, connections and relentless action all working for you, you’ll be well positioned to compete for high quality jobs in your new field. Since you chose your field, at least in part, based on your entry-level and ongoing earning potential, you’ve now crossed one of the biggest hurdles to achieving your financial sustainability. Your earnings should no longer be the limiting factor in meeting your financial needs.

Playbook Part 2 - Career Path

Selecting a Field of Work

Suggested Searches, Resources and Deeper Dives

Planning for Success in (Re)Training

Suggested Searches, Resources and Deeper Dives

Getting Your First Job in Your New Field

Suggested Searches, Resources and Deeper Dives