How To Dump Your Day Job in 10 Easy-Ish Steps

In the summer of 2015, I quit my day job as a payroll analyst for Delta Airlines and never looked back. In all honesty, I didn’t mind the job itself. Going up against tax agencies across America was a fun challenge. My job was to save Delta Airlines from overpaying taxes and fines to these agencies in about a dozen states, and occasionally, to the IRS.

What I hated about work was the people I worked with. Being the youngest woman on the team, the only one unmarried, the only one without kids, and the only one with a degree … did me zero favors. The other women on the team had it out for me and made my life a living hell. I also hated that I suddenly went from 5 months of traveling per year to just 10 business days of vacation. Ten days!

Within the first month, I wanted to leave. After a year, I decided I was done with corporate life overall. I haven’t held a corporate job since I left. I did have an easy full-time gig in 2017 to take some financial pressure off my business while I grew it. Then, I quit that too. Many people ask me how I did it and if I think they could pull it off themselves. The short answer is that it depends.

The long answer? Your ability to do so will come down to your determination, the opportunities that arise and your commitment to really getting out of the rat race. Here are 10 tips to walk you through the process.  Note that I am not a finance guru. This is based on what worked for me — twice!

1. Downsize

You might take this literally and just throw things out. This is a great first step. It’s also one of the hardest for most people. Still, it’s not enough. You also need to reduce your expenses. If you were planning to start a family, reconsider this. At the very least, consider putting this off. Thinking of getting a dog? Dogs are expensive. Get a cat or another low-maintenance pet instead.

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Comb through your bank statements. Are you paying for services you hardly ever use? When was the last time you really went to the gym? Can you get a cheaper membership? Do you even need one? Are there services you are using that you could probably do without? Start trimming that financial fat as quickly as possible.

Now, you can get to the more traditional side of downsizing. The first thing to go should be a big house or apartment. Move into something smaller. Drive a big, gas-guzzler? Get a more fuel-efficient vehicle. Then there’s getting rid of your physical things. There is no easy way to do this, but the general rule of thumb is that if you haven’t used something for six months, you probably don’t need it. Anything you’ve been holding on to for “just in case” purposes? Toss it.

Sell what you can. Give away and donate what you can’t. Place the rest in storage with your irreplaceable sentimental items. This does not have to be fancy paid storage. If you have a friend or family member who’ll let you leave a box in their attic or garage, you’re set. Use a plastic or metal container and seal everything inside as well as you can.

2. Pay Off Debt

When I ditched my day job, I had zero debt. In fact, the first debt I ever took on in my life was when I bought my car. I didn’t even have student loans. You might not be in this position, so how do you prioritize paying off debt?

There are two main strategies recommended by finance gurus. The first is called the snowball method and is especially popular among Dave Ramsey followers. With this method, you pay off the smallest debts first, so that you feel like you’re making progress. This seems more A-for-effort than practical to me. The second and more practical is to pay off the debt with the highest interest rate first.

Neither of these is ideal for dumping your day job though. Before you take financial risks — yes, this is a financial risk! — you owe it to the people who helped you to get loans to release them as your guarantors. Pay these debts off first or refinance without these generous people. Then, pay off any installment debts that take a big, mandatory chunk out of your monthly budget. After that, pay off anything you like in whatever order you like.

3. Improve Your Credit

I owe very little on my car, yet I’m holding on to the balance. Why is that? It’s the only installment loan I have. Once I pay it off, if there’s none to replace it, my credit score will fall. Think of this before you rush to pay off all your debt with fierce determination.

Even if you plan to cut up all your credit cards and go off the grid, don’t be too hasty. Credit is a godsend when managed well and you just might need it. Whether you need a new car or want to invest in the business that will help you dump your day job, chances are that a loan could work a few miracles for you. It’s better to have the option available and not need it than to need it and not qualify.

Note that the better your credit score is, the less expensive it is to borrow money. In other words, the lower your interest rate is. If your credit score currently has a few dings, work on this. Catch up on your payments. Reduce your credit utilization. Keep a good credit mix. All of these contribute to a healthy score.

4. Start Saving

Using up your credit should be a last resort. Even when a loan is necessary, the more money you have as a down payment, the lower your monthly payments will be. This is why saving is so important. You might be thinking your budget is already stretched too thin, but if you made it through the first few steps, you have plenty to save:

  • The money you save from downsizing to a smaller home
  • The money you made from selling your things
  • The extra monthly money after paying off some debt
  • The money saved by refinancing loans you can’t pay off anytime soon after improving your credit score

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Where you save your money also matters. Stay away from stocks and bonds when starting out. Stick to traditional, 100% guaranteed investments. The last thing you want is to need that money and wake up to hear the market crashed and you lost everything. Keep your money liquid. I recommend a high-interest savings account.

5. Get a Degree

If you already have a degree then you’re already way ahead. If you haven’t gotten one yet, it’s time to change that. If traditional classroom learning for 18 months to 4 years isn’t your cup of tea, then consider getting a certification in your field instead. Either way, you want some paperwork to prove you have a skill or specific know-how.

That said, it really depends on the field you go into and the clients you get. Most of my clients have, at some point, required a bachelor’s degree. My degrees in business and the liberal arts have also helped me to score higher-paying assignments that other writers were not qualified for. This was particularly true in human resources and payroll. My business major was in HR and I did a payroll certification in 2015. At the time, they told me that only about 10,000 Americans have one.

Are there certain areas where a degree or certification isn’t necessary? Absolutely. If you decide to start your own business where you target consumers (not other businesses) and don’t need technical know-how, you’ll be just fine. You might also be lucky to land a client who takes your experience over a degree.

However, the gig economy is extremely competitive. If you’re competing for job-dumping with other highly qualified contractors, you might as well do what you can to get bumped up to the head of the line.

6. Learn a Skill

A degree is worth a billion dollars when you combine it with a skill, talent and strong passion. By itself? Degrees are pretty worthless, in my opinion. Start off by finding your passion. I decided in kindergarten that I wanted a career centered on writing. What did you want to be when you grew up? You’d be surprised to learn how often your younger selves got it right in comparison to what you came up with decades later.

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Many people want to have posh skills, such as programming or architecture. I advise you not to overlook blue-collar skills. Can you build a house? Do you know how to convert cargo vans into livable recreational vehicles? Are you good at fixing cars? Do you know how to complete a full solar setup on an office or motorhome? Are you good at painting fences or exterior walls? All of these pay good money if you keep steady clients.

When choosing a skill, however, consider how you want to spend your days. If you know you’re afraid of heights, then maybe solar wiring and exterior wall painting are not for you. Don’t pick something just because you’re already good at it. You’ll end up hating it as much as your day job and want to dump it too. Still, there’s nothing wrong with making use of one sucky skill now to help you fund the one you plan to focus on later.

7. Start a Side Gig

You now have everything in place to start your side gig off on the right foot. This goes without saying, but your side gig should be based on the educational path and skills that you chose. If you work in a more technical or talent-based area, then expect to do some free or cheap work when you start off to build experience. Whatever money you do make, reinvest it in the business.

It’s also not quite time to quit your nine-to-five. Many people jump the gun, quit and regret it. If you have nothing to lose, maybe it’s worth the risk for you. Otherwise, holding on to your full-time job for a while longer ensures you never have to stress about money. You can then make better decisions for your business based on what it needs and not what your bank account needs at the time.

If you work in the field you want to branch into as a contractor, you also get more time to plan your exit and find clients who will work with you on your own. However, be careful about how you do this. You probably signed a non-compete contract. Even without this, poaching your employer’s clients will probably be bad for business. Instead, try asking the clients if they can recommend smaller businesses that could use your expertise. Also, consider asking for testimonials or references.

8. Switch to Part-Time

Can you believe it? You’re still working for your employer! What kind of madness is this? When I quit my job the first time, I went straight from payroll analyst to freelance writer. It was very stressful and I do not recommend it unless you truly feel like you have nothing to lose.

The second time around, I got an easy gig and kept lowering the hours. I worked a full-time weekend shift (yes, you read that correctly!) for a year. I then lowered it to 32 hours, and then 16. By then, my business was more than able to fill the gap. I then went down to 8 hours with another job. Quitting after that is a breeze!

The main benefit here is that you ease your business into being responsible for all your finances without hampering its growth with that burden. The next is that it fights complacency. It’s easy to get complacent when you can say you have a side gig, while your bills are still being paid by your actual 40-hours-a-week job. Switching to part-time compels you to remember who’s supposed to be your boss, soon. You!

9. Invest for the Long-Term

In number four, I cautioned you against long-term investments that tie up your money. I explained that you need that money to draw from in case of an emergency. At this point in the process, you should still be saving every penny you can. However, it’s time to also start investing in the future.

I am no finance guru, so seek advice from a financial adviser to decide how best to plan for retirement and other long-term financial goals. Will you open an IRA account? Are you now going to invest in stocks and bonds? Do you plan to rent out your home and move into a much less expensive RV?

How much money you set aside for long-term investment versus emergency funds is up to you. It can change as your needs change. There’s no need to have it all figured out now. I use Betterment for my long-term financial planning and have had no issues with it so far. I used Acorns in the past, but their fees eat away at your returns.

10. Quit Your Job

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You’ve finally made it! You improved your finances. You kicked debt in the butt. You started off small and built your clientele. You grew your portfolio and gained experience. Now, it’s time to focus on your business full time. As exciting as this sounds, it’s also scary. What if your business fails? How will you make money or recover?

This is why it’s important not to burn bridges. Poaching your employer’s clients is a sure way to burn a bridge. Also, don’t take your resignation as an opportunity to finally tell your colleagues how you really feel about them. Don’t build yourself and your business up to big heights either. You’re leaving to see if you can make something work on your own. That’s all.

While working my part-time gigs, I saw several full-timers circle right back after leaving on airs to pursue “bigger and better” things. The jokes people often shared was about how cocky they were when they walked out, only to end up in a lower position than when they left. Leave more humbly and people will feel less inclined to make your life difficult in these scenarios.

Dumping your day job won’t be easy. You won’t wake up tomorrow morning and have it suddenly all figured out. But, hopefully, you do wake up inspired. That said, don’t let anyone fool you into thinking it’s not without responsibilities. You now have to pay all your own taxes, file more complicated returns and do some serious accounting work. Still, if you prepare for the challenges ahead, you’ll do just fine — well, maybe. There are no guarantees for the new entrepreneur, but that’s part of what makes business so exciting!

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I am not a professional financial adviser. This article is based on my opinions and personal experiences. 

17 thoughts on “How To Dump Your Day Job in 10 Easy-Ish Steps

  1. It sound nice ee! Can’t say I’m necessarily looking to quit my job but I am certainly looking to have a more fulfilling career and start and build *some* degree of generational wealth. A lot of these tips are still applicable.

    1. I’m sure you’ll want to start your own practice one day! And thank you. Glad you found them useful even if they aren’t directly applicable at the moment. ☺️

  2. All great advice here. I bypassed some of these steps when I started freelancing because my main concern was getting away from the southeast. I didn’t pay off my debt because that would take years, and I didn’t have years before my mental health took another nosedive.

    But yeah, the rest. I sold my car and other possessions. I lived frugally. A coffee date was the height of luxury. The important thing is to start seeing those luxuries as luxuries – disposable, unnecessary.

  3. My advice is to never take the job in the first place that kills your soul even if it means that from the very beginning you are following all that other advice because you have to. It leaves you small sized because you never had the money to be anything else, debt free for the same reason and more content than you would have been with more of everything and that job. Worked for me! I know your advice is for those that already took said soul killing job in the first place, but I had to put in my two cents’ worth.

    1. Very good advice!

      However, any job that involves working for someone else would be a soul suck for me. It’s not the type of job; it’s the arrangement. I wouldn’t want to work as a writer or publicist for another firm. 😂 I don’t ever want to have to ask permission to take vacation ever again. I gave myself 21 paid days last year. I plan to take 30 paid days this year.

  4. Great tips. Well presented with a common sense approach. It is a little unnerving, but following your approach will help you get their. I’m looking at it for my present situation to help me save money. I’ve got a long term goal in mind. Been dithering ard too long with it. Thanks.

      1. After I retired, I wasn’t prudent in cutting back on items that I could have done without. I’m slowly getting there. Crazy thing, didn’t have an extravagant lifestyle. Just normal living expenses can kill your pocket.

      2. The simplest things can kill your budget! Been trying to explain this to mom as she’s talking about buying an even bigger house in a year or 2. She’s got another 14 years to go before retirement. I keep telling her if she wants to retire early or on time, she can’t keep living like she’s going to make her current income or more forever. Hopefully, she doesn’t have to learn the lesson the hard way. She’s been talking recently about getting a smaller home instead, but I don’t know if she’ll follow through. We’ll see! As for me, I’ll be living in about 200 SF by spring. 😅 I’m starting my retirement downsizing early!

      3. Yes I hope she will follow through on downsizing. Your money landscape changes drastically. If she can write out a plan to visualize what things will look like that might help. I learned the hard way. The earlier you start the better you’ll be in the long run. 14 years will come around very quickly.

      4. Been telling her all this. Finally coaxed her into opening a retirement savings account last year, so that’s a plus. Her finances are great right now, but she really needs to focus on setting herself up for retirement.

        Hopefully you get yours set up soon too! If you have any specific questions for me, just let me know. I’m no expert, but I’ve already started my retirement planning and can probably comment on some of what you’re trying out. 🙂

      5. Oh good. My retirement was setup because of working in federal gov’t. I was lucky from that aspect. Thanks. I will let you know. As I said good advise and steps towards a debt free life. The other post you referred to I do most of that anyway. I cook my meals, clean my own car. I am stingy about my gas too. Meaning no running around for the sake of it. My biggest expense is my mortgage. I am looking at July for my last car payment. Which I will put away and looking forward to it.

    1. Congratulations!

      I have 3 at the moment: Synchrony Bank, Betterment and Capital One. Note that the feds have dropped the interest rates and that affects savings interest rates as much as it does mortgages. At the start of the year in 2019, savings rates were around 2.45% with Synchrony and Betterment. Right now both are around 1.8%. Capital One is a fixed rate at 1%. That said, all are higher than Wells Fargo and most other traditional banks which give you around 0.1%.

      You may have other options though, so do a Google search to see if there are higher rates. These were the only 3 banks that would overlook my immigration status. Several others denied me because of the time limit that was on my green card. I haven’t gone rate shopping since becoming a citizen.

      Good luck! Let me know if I can help with anything else. 🙂

      1. Yup! We’re still on schedule. Just sorting through a different location! 🙂

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