The 10 Steps You Should Take to Get a Higher-Paying Job if You Make Less Than $50,000/year

In the 12 years I have been in the workforce, I have become exceptionally skilled at finding and landing jobs. I have held 18 of them in that time window, from “gigs” to “dead-end jobs” to “careers” to “side hustles” to “running my own (very) small business.”

In that time, I worked my way up the pay scale from $8/hour part-time ($8,000/year) to approximately $45/hour full-time ($85,000/year) in base pay when accounting for vacation time.

Obviously, this means that I am not about to start telling you how to become a millionaire. Instead, I want to talk about the smaller, more actionable first steps you can take to build a respectable career and leave the American lower class behind.

If you have ever budgeted your money and still come up short, like I did when I worked in food and retail, this is where you can start. These steps are more actionable than a millionaire lifestyle moonshot when you are living paycheck to paycheck, so they are a great way to lay the foundation for the life you want to lead.

1. Choose Your Adventure

The first step is to narrow down your options. There are infinite career paths to choose from unless we filter out the unviable possibilities. Therefore, we will focus on careers that:

  1. are lucrative enough to pay your rent.
  2. can offer stable income.
  3. can be done by most people if they achieve the necessary qualifications.
  4. do not require a graduate degree.

There are dozens of jobs that fit these criteria. Here are a few examples:

  • Engineering (software, hardware, electrical, mechanical, etc)
  • Sales (especially outside sales. Some sales jobs are commission-only, so do your homework about the pay structure)
  • Management
  • Designer (UI, UX, and Graphics)
  • Healthcare professional (radiation therapists, dental hygienists, and nuclear medicine technologists only need an Associate’s Degree to get started)
  • Operate planes and boats

I am not saying that you should give up your dreams for life to pursue one of these relatively-stable career paths. What I am saying is that the vast majority of artists, cooks, journalists, and teachers are simply not paid well in the United States. It is important to be cognizant of this reality when you are trying to pay your bills on time.

Pick a career that sounds appealing from that list, or do the research to find more options (you can start with this post, or this one, or this one). Consider the work environment, what benefits and drawbacks the field may have, and what type of work makes sense for you and the lifestyle you want. Can you imagine yourself being happy at work in that career path? Remember, this is not a commitment yet; we are simply exploring the possibility.

If you are unsure what your strengths are, as was the case for me when I decided to pursue software engineering in 2016, consider taking a personality test or two, or asking some friends what they think your key strengths are. Get an outside opinion of what makes you unique so you can see yourself through other people’s eyes.

Chances are, you are already skilled at something that will make you a good fit for a high-paying position, but you may be so good at it that you take your skill for granted!

2. Schedule an Informational Interview

Once you have picked a career you want to explore, you need to test your idea by asking someone who knows better than you. This was one of the best pieces of advice I got from the coding bootcamp I went to, Bloc:

  1. Go online. Find 25 companies that are part of the field you are interested in pursuing and put their names in a spreadsheet. Rank them on a scale from 1 to 5 These companies should be places that you would at least consider working for if they offered you a job today.
  2. Narrow these 25 down to 10 or fewer. Cut companies that require in-office work and are nowhere near you geographically (unless you would happily move to where they are); cut companies that scored 1–3 in the last step; cut companies that, after additional research, pay poorly or have bad reviews on Glassdoor. If other employees dislike them, you probably will, too.
  3. Find contact information for someone you would like to meet at these 10 companies. This could be the CEO, a founder, a hiring manager, or simply a rank-and-file employee with the job title you want to have 1–2 years from now.
  4. Follow the companies on LinkedIn and/or Twitter. Learn about what they do, what their culture is like, and figure out whether you share their values.

Then, at last, if a company is still on your list and you think you would be a good cultural fit for them, reach out to your points of contact for informational interviews, starting with the companies that interest you least. This will allow you to practice on the least-interesting ones and be prepared when you get to the companies you liked best.

What’s an informational interview, you ask? It is an opportunity for you to learn about someone, and for someone to learn about you.

When you contact the person you want to meet, ask if you can pick their brain about their company and their work for an hour if you buy them coffee. Bring about 20 questions to the interview that you genuinely want answers to. Some examples could be, “What is your day-to-day job like?”, “What do you like about Company X?”, “How does Company X stand out from the competition?”, “What are the next big opportunities for Company X?”, or “I am interested in entering this career field. What advice would you give me for how to start a career in {field} right?”

I found that the contacts at the companies I liked best were more than happy to sit down with me. The hardest part was getting them to let me pay for coffee!

A wise man once said that good business starts with a good conversation over good coffee.

Here’s what NOT to do in an informational interview:

The point is not to ask them for a job. For one, you just started pursuing this field, so you probably don’t have the qualifications anyway. But even if you do, you just met this person. The person you are talking to likely gets bombarded with requests for favors. By wanting advice, not a favor, you are establishing rapport with this person, which is far more valuable than an entry-level desk job anyway.

There are several purposes to establishing this rapport:

  • Someone in the field you are interested in now knows your name and face, and likes you. Again, why do they like you? You offered them free coffee when you met them instead of approaching with your hand out. This is tremendous leverage for when you start applying to jobs.
  • You and this influential person get the chance to evaluate each other on a friendly level, without the pressure of an interview over your head. I found my current and previous jobs at BillGO and Radial Development Group through informational interviews, but I interviewed people at several other companies who I did not align with at all! I am glad I steered clear of their companies.
  • Down the road, this person may think of you when a job opening pops up at their company. Alternatively, this person likely knows other people in the field, and you may come to mind when they hear someone else is hiring.
  • Based on this person’s responses, you can evaluate whether you are making a good decision. Does this person hate their job? Does this person suggest that you stay away from the field? Are they thrilled by their work, or cynical about where they landed? If they sound displeased, try another company on your list. If everyone in the field hates their job, maybe that field is full of toxic people in your area, and you should consider picking a different path!

If you are worried about wasting this person’s time, do your homework. Research their company, the industry, and, if you can, the person you will be speaking to. Bring smart questions, not offhand ones. Show that you value their time. They will love you for it!

3. Commit to the Path

Now you have to make a decision. Are you going to commit to this career choice?

If you find yourself needing more clarity, see if you can get some firsthand experience working in the field. Can you job shadow someone? Can you do some practice lessons online? Try actually doing the job for a day, as described by the informational interviewee, and see if you like it.

If the work seems decent, you probably found a good option. If the work is like nails on a chalkboard, it is probably not right.

A few key points to keep in mind:

  • No job, of any kind, is always fun. There will be parts you dislike even in a career that is your true calling.
  • I am okay with the work feeling “acceptable” when you first try it. It will probably be better at a good company you click with once you are there. When you build relationships with coworkers and see what the day-to-day is really like, it will feel less foreign and uncomfortable than a brand-new career path.
  • You should not judge the work by whether you are good at it. Spoiler alert: you are going to be terrible at it at first, and that is okay! How could you possibly be good at it? You just started.

But the most important rule is this: commit to the career path for five years. Yup, five. Why? If you bail out before five, you are likely bailing because of one bad circumstance or because you struggled with the work right out of the gate (which is not a good reason to quit). After five years, you will truly know whether the career is right for you. If you hate it, go do something else. You can have many careers if you want to!

4. Begin Acquiring the Skills You Need

Hopefully your informational interviewees pointed you toward a place where you can get the skills you need. If not, do some research online about where you can. For me, this was Bloc, but there are trade schools and hands-on training programs for most of the career paths I mentioned.

Some lucrative careers I did not mention (becoming a lawyer or a surgeon, for example) require a college degree, which is typically a longer time commitment than I recommend if you need to raise your standard of living soon. However, if you think you can make ends meet for four or more years, you have far more options available to you.

Do not pick the first thing you see. As with the list of companies we made earlier, get a list of potential candidates and compare their price, value, and reviews. Education can be exorbitantly expensive in the United States, but there are often ways to get around it. For example, if you decided on a career that requires a four-year degree after all, consider working as a TA through college. My sister gets paid for it and gets her tuition paid for by the school!

5. Get a Mentor to Hold You Accountable

Bloc hooked me up with a mentor all on its own, but one way or the other, you should get a mentor. The people who are the best in their field get mentors, and you should, too. This could be one of your informational interviewees, a teacher in your learning program, or someone you admire and want to emulate.

The purpose of getting a mentor is that it is hard to push yourself to work on a new skill every day, or at least on weekdays. Accountability will force you to keep going when it gets tough and give you goals to aim at. Don’t work in the dark.

6. Network Iteratively

Continue to schedule informational interviews. They should not sidetrack your learning program, but an occasional interview will give you practice networking and talking about your new field. By doing this, I got a job before I even completed my Bloc coursework.

It is also worth spending a little time every week seeking out online forums (or in-person events, post-COVID) where you can network with people in your field. There is a strong possibility that you will find companies and opportunities this way that have smaller online presences. Lots of companies are focused on their local community, and they can be the best places to start a new career!

7. Search for Great Learning Environments

As you acquire the skills you need and network with people in the industry, be on the lookout for places that are great learning environments. This can be either a company or one of those online forums I mentioned with a friendly community of people, happy to help you problem-solve.

Your first job in the field does not need to be the #1 dream job in your spreadsheet. You can always work toward that as you go. In fact, if your dream job is a position at a huge company, it is probably the wrong place to start. The bigger a company is, the more the responsibilities are split into bite-sized pieces, and the less entry-level team members see the overall picture. Starting at a small company can expose you to all aspects of the business, and that can in turn qualify you for a higher position at your dream company.

8. Help Others Before They Help You

Once you start getting comfortable with the skills you’re learning, focus on helping others, not on getting help. For example, in the software community, contributing to open-source projects (projects that anyone can see the code for and contribute to) is a great way to gain exposure and make a positive impact for others.

As with the informational interviews, your goal is not to come to people with your hand out. The best way to get things from people is to give them things first; humans are just wired that way! Offer to pitch in on a project that is relevant to someone in the industry or a company on your list.

9. Apply When You Know You Stand Out

Impostor syndrome is difficult to work through when you are new to a field. In my case, I could not help but feel like I was not really qualified to write software when I finished my coding bootcamp. But try to evaluate yourself honestly: what do I know six months’ into my training that I did not know when I started? What can I do that I could not do before? Who do I know in this industry that I had never met before I started?

A common piece of advice is to apply to jobs whether you think you are qualified or not. I am sure that this has worked for some people; sometimes no one (or no one qualified) applies to an opening, and you are the best option! But this is not what has worked for me.

In my experience, my persistence and passion gets me jobs, not luck. In many cases, I have applied to a job, been rejected, applied again not long after, and gotten the job the second time. The first round gives me practice and confidence; by the second one, I am more than ready for the job I want.

Of course, you have to figure out what works for you, but I would encourage you to leverage every tool available to you (networking, technical skill, and relevant life experience from other jobs) to stand out from the crowd when applying.

Once you feel ready, apply. If you have followed all of the steps above, you will have a qualifying skillset and have tipped the odds in your favor by knowing someone at the company you applied to. If you are turned down, be sure to ask for feedback on how you can improve. You may not get it every time, but you will definitely expedite your job search when you do and leave a good impression behind.

10. Listen to Yourself First

Through all of these steps, one of the most important things to remember is that people like to criticize until they see success. You will likely tell people around you that you are going to go be a software engineer, or get a pilot’s license, or become a realtor or graphic designer, only to be met with skepticism.

The reason is that they have not done what you are setting out to do, and they will have plenty of reasons why.

  • Pursuing that path is expensive!
  • You have to be really smart to do that!
  • The work hours will be long!
  • It is a huge commitment!

Don’t listen to them.

They have not seen you in action yet.

They do not know what you are capable of.

And don’t worry; once they see your success, they will say they supported you all along.

Your voice comes first. Listen to how you feel about your choice, even if those feelings contradict your friends’ and family’s input, or even the input from this post.

Do what’s right for you.

Originally published at on September 21, 2020.



I write about personal finance, career growth, and making the most of the new workforce. You can find my blog at

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Dan Rice

I write about personal finance, career growth, and making the most of the new workforce. You can find my blog at