Quit Your Way to Success: 6 People Who Left Their Jobs to Make More Money on Their Own

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The horrible job. We’ve all had one.

The one that has you dreading Monday as early as Sunday morning. The one that has you plotting dramatic “I quit” scenarios while you’re taking your morning shower. The one that has you asking yourself “What am I doing here?” every few days.

The worst part is feeling stuck. Maybe you can’t find another job. Maybe you’re not even sure where to look. You fear your fate is sealed forever.

The good news is many people have been in your shoes and managed to escape. Want proof? Below are six stories of people who not only quit their jobs but also ended up earning more. Here’s how they did it.

It might be time to leave when you wish for a sick day …

Sometimes a job isn’t bad; it’s just the wrong thing for you. Or it was the right thing until stagnation kicked in.

That’s what happened to freelance writer and content strategist Kayla Albert. After working in the same role for several years in her hometown of Denver, she realized it was time to move on.

“One Monday morning, I woke up hoping I was sick just so I wouldn’t have to go into the office,” Albert said. “That’s when it became clear I needed to make a change.”

Luckily, she was already doing freelance work on the side, so she began to focus more of her energy there in order to plan a transition.

“I wanted to have close to one year’s salary saved before making the leap,” she said. “It helped ease my mind as much as possible.”

Albert decided she’d be able to save enough to quit in three months, which the freelance work helped her do. And it didn’t take up so much of her time that she couldn’t have a life. Between her full-time work and freelancing, she was clocking a reasonable 45 to 47 hours per week.

She also told her network outside her immediate workplace about the upcoming change. This move is not only a good idea for building new clients; it also can help you follow through on your plans. Albert’s network helped her stay on track and remain strong.

For aspiring solopreneurs, Albert suggested a focus on preparation.

“Start planning now,” she said. “Even if you think tackling your dream is five years into the future, setting aside the money now will allow you to take the leap when you know it’s time instead of muscling through a not-so-great work situation.”

It’s been more than a year since Albert took the leap, and she’s already outpaced her previous salary by 8 to 10 percent. Even better, she works 25 hours per week instead of 40. For someone seeking a better work-life balance, it’s the ultimate gain.

Another strategy that helped Albert was opening a business checking account so she could keep her business earnings separate and pay herself a salary. This move made it easier to budget the way she did when she had a full-time job. And the budgeting is even better now that her income is on the rise.

… Or when work is taking over your life

Speaking of muscling through a not-so-great work situation, what happens if your job is taking over your life? When this happened to financial writer Kali Hawlk, she knew it was time to leave.

“Your work is clearly important — but it shouldn’t run your life,” she said. “And it certainly shouldn’t make you miserable ALL the time.”

Hawlk practices what she preaches in terms of taking risks for happiness. While she was working toward her goal of self-employment, she picked up her Southern roots and fulfilled her dream of moving to Boston.

Now she loves her work life and home life equally, as she’s able to work for herself and then go out and enjoy her adopted city.

Hawlk’s biggest focus as she made the transition was building her business to a reasonable size before taking the leap. Doing so provided some assurance that the business plan was sound and the success was replicable.

And all that extra work paid off when it led her to a big enough client base that she could go full time on her own.

“I wanted to earn at least twice as much from my own business as I earned from my job — to account for things like expenses, taxes, etc.  and I wanted to do that for at least three months in a row before I felt comfortable enough to go back out on my own,” she said.

As Hawlk thinks about her progress from working full time to building a business of her own, she’s pleased with how well things are going. She has not only fulfilled her dream of becoming her own boss, but she’s also earning enough to do it in the city of her dreams.

Now that’s turning an unhappy scenario into a win.

… Or when you realize you have a chance at self-employment

Unhappiness is one reason to leave a job, but so is the moment you realize you might have what it takes to start your own venture. When Careful Cents owner Carrie Smith Nicholson had that realization, everything changed.

“I didn’t set out to quit my job and be my own boss, but after spending two years with my blogging side hustle, I could see the potential to take it full time,” she said.

Like Albert and Hawlk, Smith Nicholson wasn’t going to leave before her finances were ready. She wanted to save $10,000 first — a number she came to after adding up her monthly expenses. But when she hit $8,000, a family member experienced a health issue that made her realize she was close enough. So she put in her notice.

Four years later, Smith Nicholson’s business is booming. She’s already doubled her previous income and is on track to triple it. What’s more, she’s turning her business success into a way to help others do the same. Her blog, which used to be focused on personal finance, now helps others achieve their entrepreneurial dreams.

By helping people achieve freedom from the cubicle, Smith Nicholson is living a life of happiness and giving.

But she encouraged those who want to do the same to be practical: “My advice is to have a solid business plan in place. How are you going to make money? Does this revenue model fit into the kind of lifestyle you want to create?”

If you don’t answer those questions honestly, you might end up having to go back to a regular job. A little planning — both for the business and your finances — can go a long way to ensure the sustainability of your dream.

More ways you can prepare for becoming your own boss

It isn’t easy to quit your job and start your own venture — and you might have a few sleepless nights before it all comes together. Here are a few things you can do to prepare yourself for what’s ahead.

Get ready for some financial sacrifices

David Waring, father of two young children and founder of business review company Fit Small Business, quit his job as an executive selling institutional trading software to banks and hedge funds in 2011.

Waring now earns roughly 50 percent more with his own company than he did then as a sales executive.

But he knew it could take several years to reach success, so he built his business while working full time. He also saved up $40,000 and traded his Wall Street luxury apartment for a roommate and a walk-up in Harlem.

One key for David was not spending too much money at the beginning — a strategy that dovetailed with his frugal ways.

“I chose a great business partner,” he explained. “We did not invest a lot of money initially and let the idea prove itself on its own merit. Once things started working, we invested most of the profit back into growing the business.”

Grow your industry knowledge and your network

Lily Taban, founder of public relations consulting company Fig & First, used her knowledge and network to get a business off the ground.

Lily’s first referral came through a friend and former co-worker who appreciated her experience and passion. And her business has grown on referrals ever since.

If you have a solid list of personal contacts in your industry, reaching out to them to build a client base can be a great way to start. But make sure you don’t hedge your bets so much that you never take the plunge.

“I was always waiting to be ‘ready,’ and I would have lived my entire life waiting,” she said. “There was always a fear or excuse holding me back from making the leap to work for myself.”

Prepare yourself financially and professionally, but remember: At some point, you’re going to have to leap.

Prepare to make some mistakes

One of the hardest parts of working for yourself is how much time you spend doing things besides the thing you earn money for.

Matthew Keesan, co-founder of Raaka Chocolate, learned that the hard way. Although he didn’t want for clients in the beginning — he was able to turn the job he hated into a contract with the company he worked for, earning three times more — the pressures of operating a business were still there.

“I learned, painfully, how to run a business — managing cash flow, managing client expectations, ensuring I got paid on time, etc.,” he said. “It was easy starting with a client who was my former employer who didn’t want to see me go.”

But in the end, he got his ultimate payoff.

“I’ve been fortunate to get to work in a variety of industries, from finance to hospitality to technology, but the sweetest work of all is being my own boss,” he said.

Want to take your own leap? Start planning

It might be difficult to imagine quitting your job and then earning enough to double, triple, or even quadruple your income. But as you can see here, it’s been done before, and it can be done again.

It all comes down to understanding how much money you’ll need to earn, working on building a client base before you leap, and doing research on what it takes to run a business.

Want even more ideas? Check out this story for tips on how to turn a side gig into a full-fledged business.

Interested in refinancing student loans?

Here are the top 6 lenders of 2018!
LenderVariable APREligible Degrees 
Check out the testimonials and our in-depth reviews!
1 Important Disclosures for Earnest.

Earnest Disclosures

To qualify, you must be a U.S. citizen or possess a 10-year (non-conditional) Permanent Resident Card, reside in a state Earnest lends in, and satisfy our minimum eligibility criteria. You may find more information on loan eligibility here: https://www.earnest.com/eligibility. Not all applicants will be approved for a loan, and not all applicants will qualify for the lowest rate. Approval and interest rate depend on the review of a complete application.

Earnest fixed rate loan rates range from 3.89% APR (with Auto Pay) to 7.89% APR (with Auto Pay). Variable rate loan rates range from 2.47% APR (with Auto Pay) to 6.97% APR (with Auto Pay). For variable rate loans, although the interest rate will vary after you are approved, the interest rate will never exceed 8.95% for loan terms 10 years or less. For loan terms of 10 years to 15 years, the interest rate will never exceed 9.95%. For loan terms over 15 years, the interest rate will never exceed 11.95% (the maximum rates for these loans). Earnest variable interest rate loans are based on a publicly available index, the one month London Interbank Offered Rate (LIBOR). Your rate will be calculated each month by adding a margin between 1.82% and 5.50% to the one month LIBOR. The rate will not increase more than once per month. Earnest rate ranges are current as of Month/Day/Year, and are subject to change based on market conditions and borrower eligibility.

Auto Pay discount: If you make monthly principal and interest payments by an automatic, monthly deduction from a savings or checking account, your rate will be reduced by one quarter of one percent (0.25%) for so long as you continue to make automatic, electronic monthly payments. This benefit is suspended during periods of deferment and forbearance.

The information provided on this page is updated as of 08/21/18. Earnest reserves the right to change, pause, or terminate product offerings at any time without notice. Earnest loans are originated by Earnest Operations LLC. California Finance Lender License 6054788. NMLS # 1204917. Earnest Operations LLC is located at 302 2nd Street, Suite 401N, San Francisco, CA 94107. Terms and Conditions apply. Visit https://www.earnest.com/terms-of-service, email us at hello@earnest.com, or call 888-601-2801 for more information on ourstudent loan refinance product.

© 2018 Earnest LLC. All rights reserved. Earnest LLC and its subsidiaries, including Earnest Operations LLC, are not sponsored by or agencies of the United States of America.


2 Important Disclosures for Laurel Road.

Laurel Road Disclosures

APR stands for “Annual Percentage Rate.” Rates listed include a 0.25% EFT discount, for automatic payments made from a checking or savings account. Interest rates as of 11/8/2018. Rates subject to change.

Variable rate options consist of a range from 3.27% per year to 6.09% per year for a 5-year term, 4.64% per year to 6.14% per year for a 7-year term, 4.69% per year to 6.19% per year for a 10-year term, 4.94% per year to 6.44% per year for a 15-year term, or 5.19% per year to 6.69% per year for a 20-year term, with no origination fees. APR is subject to increase after consummation. The variable interest rate will change on the first day of every month (“Change Date”) if the Current Index changes. The variable interest rates are based on a Current Index, which is the 1-month London Interbank Offered Rate (LIBOR) (currency in US dollars), as published on The Wall Street Journal’s website. The variable interest rates and Annual Percentage Rate (APR) will increase or decrease when the 1-month LIBOR index changes. The variable interest rates are calculated by adding a margin ranging from 0.98% to 3.80% for the 5-year term loan, 2.35% to 3.85% for the 7-year term loan, 2.40% to 3.90% for the 10-year term loan, 2.65% to 4.15% for the 15-year term loan, and 2.90% to 4.40% for the 20-year term loan, respectively, to the 1-month LIBOR index published on the 25th day of each month immediately preceding each “Change Date,” as defined above, rounded to two decimal places, with no origination fees. If the 25th day of the month is not a business day or is a US federal holiday, the reference date will be the most recent date preceding the 25th day of the month that is a business day. The monthly payment for a sample $10,000 loan at a range of 3.27% per year to 6.09% per year for a 5-year term would be from $180.89 to $193.75. The monthly payment for a sample $10,000 loan at a range of 4.64% per year to 6.14% per year for a 7-year term would be from $139.65 to $146.76. The monthly payment for a sample $10,000 loan at a range of 4.69% per year to 6.19% per year for a 10-year term would be from $104.56 to $111.98. The monthly payment for a sample $10,000 loan at a range of 4.94% per year to 6.44% per year for a 15-year term would be from $78.77 to $86.78. The monthly payment for a sample $10,000 loan at a range of 5.19% per year to 6.69% per year for a 20-year term would be from $67.05 to $75.68.

However, if the borrower chooses to make monthly payments automatically by electronic funds transfer (EFT) from a bank account, the variable rate will decrease by 0.25%, and will increase back up to the regular variable interest rate described in the preceding paragraph if the borrower stops making (or we stop accepting) monthly payments automatically by EFT from the designated borrower’s bank account.


3 Important Disclosures for SoFi.

SoFi Disclosures

  1. Student loan Refinance:
    Fixed rates from 3.899% APR to 7.979% APR (with AutoPay). Variable rates from 2.470% APR to 6.990% APR (with AutoPay). Interest rates on variable rate loans are capped at either 8.95% or 9.95% depending on term of loan. See APR examples and terms. Lowest variable rate of 2.470% APR assumes current 1 month LIBOR rate of 2.30% plus 0.91% margin minus 0.25% ACH discount. Not all borrowers receive the lowest rate. If approved for a loan, the fixed or variable interest rate offered will depend on your creditworthiness, and the term of the loan and other factors, and will be within the ranges of rates listed above. For the SoFi variable rate loan, the 1-month LIBOR index will adjust monthly and the loan payment will be re-amortized and may change monthly. APRs for variable rate loans may increase after origination if the LIBOR index increases. The SoFi 0.25% AutoPay interest rate reduction requires you to agree to make monthly principal and interest payments by an automatic monthly deduction from a savings or checking account. The benefit will discontinue and be lost for periods in which you do not pay by automatic deduction from a savings or checking account. *To check the rates and terms you qualify for, SoFi conducts a soft credit inquiry. Unlike hard credit inquiries, soft credit inquiries (or soft credit pulls) do not impact your credit score. Soft credit inquiries allow SoFi to show you what rates and terms SoFi can offer you up front. After seeing your rates, if you choose a product and continue your application, we will request your full credit report from one or more consumer reporting agencies, which is considered a hard credit inquiry. Hard credit inquiries (or hard credit pulls) are required for SoFi to be able to issue you a loan. In addition to requiring your explicit permission, these credit pulls may impact your credit score.
  2. Terms and Conditions Apply. SOFI RESERVES THE RIGHT TO MODIFY OR DISCONTINUE PRODUCTS AND BENEFITS AT ANY TIME WITHOUT NOTICE. To qualify, a borrower must be a U.S. citizen or permanent resident in an eligible state and meet SoFi’s underwriting requirements. Not all borrowers receive the lowest rate. To qualify for the lowest rate, you must have a responsible financial history and meet other conditions. If approved, your actual rate will be within the range of rates listed above and will depend on a variety of factors, including term of loan, a responsible financial history, years of experience, income and other factors. Rates and Terms are subject to change at anytime without notice and are subject to state restrictions. SoFi refinance loans are private loans and do not have the same repayment options that the federal loan program offers such as Income Based Repayment or Income Contingent Repayment or PAYE. Licensed by the Department of Business Oversight under the California Financing Law License No. 6054612. SoFi loans are originated by SoFi Lending Corp., NMLS # 1121636. (www.nmlsconsumeraccess.org)

4 Important Disclosures for LendKey.

LendKey Disclosures

Refinancing via LendKey.com is only available for applicants with qualified private education loans from an eligible institution. Loans that were used for exam preparation classes, including, but not limited to, loans for LSAT, MCAT, GMAT, and GRE preparation, are not eligible for refinancing with a lender via LendKey.com. If you currently have any of these exam preparation loans, you should not include them in an application to refinance your student loans on this website. Applicants must be either U.S. citizens or Permanent Residents in an eligible state to qualify for a loan. Certain membership requirements (including the opening of a share account and any applicable association fees in connection with membership) may apply in the event that an applicant wishes to accept a loan offer from a credit union lender. Lenders participating on LendKey.com reserve the right to modify or discontinue the products, terms, and benefits offered on this website at any time without notice. LendKey Technologies, Inc. is not affiliated with, nor does it endorse, any educational institution.


5 Important Disclosures for CommonBond.

CommonBond Disclosures

Offered terms are subject to change. Loans are offered by CommonBond Lending, LLC (NMLS # 1175900). If you are approved for a loan, the interest rate offered will depend on your credit profile, your application, the loan term selected and will be within the ranges of rates shown.

All Annual Percentage Rates (APRs) displayed assume borrowers enroll in auto pay and account for the 0.25% reduction in interest rate. All variable rates are based on a 1-month LIBOR assumption of 2.28% effective October 10, 2018.


6 Important Disclosures for Citizens Bank.

Citizens Bank Disclosures

  1. Education Refinance Loan Rate Disclosure: Variable rate, based on the one-month London Interbank Offered Rate (“LIBOR”) published in The Wall Street Journal on the twenty-fifth day, or the next business day, of the preceding calendar month. As of November 1, 2018, the one-month LIBOR rate is 2.29%. Variable interest rates range from 2.79%-8.39% (2.79%-8.39% APR) and will fluctuate over the term of the borrower’s loan with changes in the LIBOR rate, and will vary based on applicable terms, level of degree earned and presence of a cosigner. Fixed interest rates range from 3.75%-8.69% (3.75%-8.69% APR) based on applicable terms, level of degree earned and presence of a cosigner. Lowest rates shown require application with a cosigner, are for eligible, creditworthy applicants with a graduate level degree, require a 5-year repayment term and include our Loyalty discount and Automatic Payment discounts of 0.25 percentage points each, as outlined in the Loyalty and Automatic Payment Discount disclosures. The maximum variable rate on the Education Refinance Loan is the greater of 21.00% or Prime Rate plus 9.00%. Subject to additional terms and conditions, and rates are subject to change at any time without notice. Such changes will only apply to applications taken after the effective date of change. Please note: Due to federal regulations, Citizens Bank is required to provide every potential borrower with disclosure information before they apply for a private student loan. The borrower will be presented with an Application Disclosure and an Approval Disclosure within the application process before they accept the terms and conditions of their loan.
  2. Federal Loan vs. Private Loan Benefits: Some federal student loans include unique benefits that the borrower may not receive with a private student loan, some of which we do not offer with the Education Refinance Loan. Borrowers should carefully review their current benefits, especially if they work in public service, are in the military, are currently on or considering income based repayment options or are concerned about a steady source of future income and would want to lower their payments at some time in the future. When the borrower refinances, they waive any current and potential future benefits of their federal loans and replace those with the benefits of the Education Refinance Loan. For more information about federal student loan benefits and federal loan consolidation, visit http://studentaid.ed.gov/. We also have several resources available to help the borrower make a decision at http://www.citizensbank.com/EdRefinance, including Should I Refinance My Student Loans? and our FAQs. Should I Refinance My Student Loans? includes a comparison of federal and private student loan benefits that we encourage the borrower to review.
  3. Citizens Bank Education Refinance Loan Eligibility: Eligible applicants may not be currently enrolled. Applicants with an Associate’s degree or with no degree must have made at least 12 qualifying payments after leaving school. Qualifying payments are the most recent on time and consecutive payments of principal and interest on the loans being refinanced. Primary borrowers must be a U.S. citizen, permanent resident or resident alien with a valid U.S. Social Security Number residing in the United States. Resident aliens must apply with a cosigner who is a U.S. citizen or permanent resident. The cosigner (if applicable) must be a U.S. citizen or permanent resident with a valid U.S. Social Security Number residing in the United States. For applicants who have not attained the age of majority in their state of residence, a cosigner will be required. Citizens Bank reserves the right to modify eligibility criteria at anytime. Interest rate ranges subject to change. Education Refinance Loans are subject to credit qualification, completion of a loan application/consumer credit agreement, verification of application information, certification of borrower’s student loan amount(s) and highest degree earned.
  4. Loyalty Discount Disclosure: The borrower will be eligible for a 0.25 percentage point interest rate reduction on their loan if the borrower or their co-signer (if applicable) has a qualifying account in existence with us at the time the borrower and their co-signer (if applicable) have submitted a completed application authorizing us to review their credit request for the loan. The following are qualifying accounts: any checking account, savings account, money market account, certificate of deposit, automobile loan, home equity loan, home equity line of credit, mortgage, credit card account, or other student loans owned by Citizens Bank, N.A. Please note, our checking and savings account options are only available in the following states: CT, DE, MA, MI, NH, NJ, NY, OH, PA, RI, and VT and some products may have an associated cost. This discount will be reflected in the interest rate disclosed in the Loan Approval Disclosure that will be provided to the borrower once the loan is approved. Limit of one Loyalty Discount per loan and discount will not be applied to prior loans. The Loyalty Discount will remain in effect for the life of the loan.
  5. Automatic Payment Discount Disclosure: Borrowers will be eligible to receive a 0.25 percentage point interest rate reduction on their student loans owned by Citizens Bank, N.A. during such time as payments are required to be made and our loan servicer is authorized to automatically deduct payments each month from any bank account the borrower designates. Discount is not available when payments are not due, such as during forbearance. If our loan servicer is unable to successfully withdraw the automatic deductions from the designated account three or more times within any 12-month period, the borrower will no longer be eligible for this discount.
  6. Co-signer Release: Borrowers may apply for co-signer release after making 36 consecutive on-time payments of principal and interest. For the purpose of the application for co-signer release, on-time payments are defined as payments received within 15 days of the due date. Interest only payments do not qualify. The borrower must meet certain credit and eligibility guidelines when applying for the co-signer release. Borrowers must complete an application for release and provide income verification documents as part of the review. Borrowers who use deferment or forbearance will need to make 36 consecutive on-time payments after reentering repayment to qualify for release. The borrower applying for co-signer release must be a U.S. citizen or permanent resident. If an application for co-signer release is denied, the borrower may not reapply for co-signer release until at least one year from the date the application for co-signer release was received. Terms and conditions apply.

2.47% – 6.99%3Undergrad
& Graduate

Visit SoFi

2.46% – 6.97%1Undergrad
& Graduate

Visit Earnest

2.57% – 8.09%4Undergrad
& Graduate

Visit Lendkey

3.02% – 6.44%2Undergrad
& Graduate

Visit Laurel Road

2.50% – 7.24%5Undergrad
& Graduate

Visit CommonBond

2.79% – 8.39%6Undergrad
& Graduate

Visit Citizens

Our team at Student Loan Hero works hard to find and recommend products and services that we believe are of high quality and will make a positive impact in your life. We sometimes earn a sales commission or advertising fee when recommending various products and services to you. Similar to when you are being sold any product or service, be sure to read the fine print understand what you are buying, and consult a licensed professional if you have any concerns. Student Loan Hero is not a lender or investment advisor. We are not involved in the loan approval or investment process, nor do we make credit or investment related decisions. The rates and terms listed on our website are estimates and are subject to change at any time. Please do your homework and let us know if you have any questions or concerns.