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

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Our team at Student Loan Hero works hard to find and recommend products and services that we believe are of high quality. 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 to help you understand what you are buying. Be sure to consult with 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.

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quitting your job

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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 8 lenders of 2020!
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 3.20% APR (with Auto Pay) to 6.99% APR (with Auto Pay). Variable rate loan rates range from 1.99% APR (with Auto Pay) to 6.89% 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 December 13, 2019, 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 12/13/2019. 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 our student 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 SoFi.

SoFi Disclosures

  1. Student loan Refinance: Fixed rates from 3.46% APR (with AutoPay) to 7.61% APR (without AutoPay). Variable rates currently from 2.31% APR (with AutoPay) to 7.61% (without 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 2.31% APR assumes current 1 month LIBOR rate of 2.31% plus 0.75% margin minus 0.25% for AutoPay. If approved for a loan, the fixed or variable interest rate offered will depend on your credit history and the term of the loan 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.

3 Important Disclosures for Figure.

Figure Disclosures

Figure’s Student Refinance Loan is a private loan. If you refinance federal loans, you forfeit certain flexible repayment options associated with those loans. If you expect to incur financial hardship that would impact your ability to repay, you should consider federal consolidation alternatives.

4 Important Disclosures for College Ave.

College Ave Disclosures

College Ave Student Loans products are made available through either Firstrust Bank, member FDIC or M.Y. Safra Bank, FSB, member FDIC. All loans are subject to individual approval and adherence to underwriting guidelines. Program restrictions, other terms, and conditions apply.

1College Ave Refi Education loans are not currently available to residents of Maine.

2All rates shown include autopay discount. The 0.25% auto-pay interest rate reduction applies as long as a valid bank account is designated for required monthly payments. Variable rates may increase after consummation.

3$5,000 is the minimum requirement to refinance. The maximum loan amount is $300,000 for those with medical, dental, pharmacy or veterinary doctorate degrees, and $150,000 for all other undergraduate or graduate degrees.

4This informational repayment example uses typical loan terms for a refi borrower with a Full Principal & Interest Repayment and a 10-year repayment term, has a $40,000 loan and a 5.5% Annual Percentage Rate (“APR”): 120 monthly payments of $434.11 while in the repayment period, for a total amount of payments of $52,092.61. Loans will never have a full principal and interest monthly payment of less than $50. Your actual rates and repayment terms may vary.

Information advertised valid as of 1/1/2020. Variable interest rates may increase after consummation.

5 Important Disclosures for Laurel Road.

Laurel Road Disclosures

Laurel Road is a brand of KeyBank National Association offering online lending products in all 50 U.S. states, Washington, D.C., and Puerto Rico. Mortgage lending is not offered in Puerto Rico. All loans are provided by KeyBank National Association.
As used throughout these Terms & Conditions, the term “Lender” refers to KeyBank National Association and its affiliates, agents, guaranty insurers, investors, assigns, and successors in interest.

This term represents the actual cost of financing to the borrower over the life of the loan expressed as a yearly rate.


There are no origination fees or prepayment penalties associated with the loan. Lender may assess a late fee if any part of a payment is not received within 15 days of the payment due date. Any late fee assessed shall not exceed 5% of the late payment or $28, whichever is less. A borrower may be charged $20 for any payment (including a check or an electronic payment) that is returned unpaid due to non-sufficient funds (NSF) or a closed account.


For bachelor’s degrees and higher, up to 100% of outstanding private and federal student loans (minimum $5,000) are eligible for refinancing. If you are refinancing greater than $300,000 in student loan debt, Lender may refinance the loans into 2 or more new loans.
For eligible Associates degrees in the healthcare field (see Eligibility & Eligible Loans section below), Lender will refinance up to $50,000 in loans for non-ParentPlus refinance loans. Note, parents who are refinancing loans taken out on behalf of a child who has obtained an associates degrees in an eligible healthcare field are not subject to the $50,000 loan maximum, refer to https://www.laurelroad.com/refinance-student-loans/refinance-parent-plus-loans/ for more information about refinancing ParentPlus loans.


Borrower, and Co-signer if applicable, must be a U.S. Citizen or Permanent Resident with a valid I-551 card (which must show a minimum of 10 years between “Resident Since” date and “Card Expires” date or has no expiration date); state that they are of at least borrowing age in the state of residence at the time of application; and meet Lender underwriting criteria (including, for example, employment, debt-to-income, disposable income, and credit history requirements).

Graduates may refinance any unsubsidized or subsidized Federal or private student loan that was used exclusively for qualified higher education expenses (as defined in 26 USC Section 221) at an accredited U.S. undergraduate or graduate school. Any federal loans refinanced with Lender are private loans and do not have the same repayment options that federal loan program offers such as Income Based Repayment or Income Contingent Repayment.

All loans must be in grace or repayment status and cannot be in default. Borrower must have graduated or be enrolled in good standing in the final term preceding graduation from an accredited Title IV U.S. school and must be employed, or have an eligible offer of employment. Parents looking to refinance loans taken out on behalf of a child should refer to https://www.laurelroad.com/refinance-student-loans/refinance-parent-plus-loans/ for applicable terms and conditions.

For Associates Degrees: Only associates degrees earned in one of the following are eligible for refinancing: Cardiovascular Technologist (CVT); Dental Hygiene; Diagnostic Medical Sonography; EMT/Paramedics; Nuclear Technician; Nursing; Occupational Therapy Assistant; Pharmacy Technician; Physical Therapy Assistant; Radiation Therapy; Radiologic/MRI Technologist; Respiratory Therapy; or Surgical Technologist. To refinance an Associates degree, a borrower must also either be currently enrolled and in the final term of an associate degree program at a Title IV eligible school with an offer of employment in the same field in which they will receive an eligible associate degree OR have graduated from a school that is Title IV eligible with an eligible associate and have been employed, for a minimum of 12 months, in the same field of study of the associate degree earned.


The interest rate you are offered will depend on your credit profile, income, and total debt payments as well as your choice of fixed or variable and choice of term. For applicants who are currently medical or dental residents, your rate offer may also vary depending on whether you have secured employment for after residency.


The repayment of any refinanced student loan will commence (1) immediately after disbursement by us, or (2) after any grace or in-school deferment period, existing prior to refinancing and/or consolidation with us, has expired.


After loan disbursement, if a borrower documents a qualifying economic hardship, we may agree in our discretion to allow for full or partial forbearance of payments for one or more 3-month time periods (not to exceed 12 months in the aggregate during the term of your loan), provided that we receive acceptable documentation (including updating documentation) of the nature and expected duration of the borrower’s economic hardship.

We may agree under certain circumstances to allow a borrower to make $100/month payments for a period of time immediately after loan disbursement if the borrower is employed full-time as an intern, resident, or similar postgraduate trainee at the time of loan disbursement. These payments may not be enough to cover all of the interest that accrues on the loan. Unpaid accrued interest will be added to your loan and monthly payments of principal and interest will begin when the post-graduate training program ends.

We may agree under certain circumstances to allow postponement (deferral) of monthly payments of principal and interest for a period of time immediately following loan disbursement (not to exceed 6 months after the borrower’s graduation with an eligible degree), if the borrower is an eligible student in the borrower’s final term at the time of loan disbursement or graduated less than 6 months before loan disbursement, and has accepted an offer of (or has already begun) full-time employment.

If Lender agrees (in its sole discretion) to postpone or reduce any monthly payment(s) for a period of time, interest on the loan will continue to accrue for each day principal is owed. Although the borrower might not be required to make payments during such a period, the borrower may continue to make payments during such a period. Making payments, or paying some of the interest, will reduce the total amount that will be required to be paid over the life of the loan. Interest not paid during any period when Lender has agreed to postpone or reduce any monthly payment will be added to the principal balance through capitalization (compounding) at the end of such a period, one month before the borrower is required to resume making regular monthly payments.


This information is current as of November 8, 2019 and is subject to change.

6 Important Disclosures for Splash Financial.

Splash Financial Disclosures

Terms and Conditions apply. Splash reserves the right to modify or discontinue products and benefits at any time without notice. Rates and terms are also subject to change at any time without notice. Offers are subject to credit approval. To qualify, a borrower must be a U.S. citizen or permanent resident in an eligible state and meet applicable underwriting requirements. Not all borrowers receive the lowest rate. Lowest rates are reserved for the highest qualified borrowers.

7 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 1.76% effective November 10, 2019.

8 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.

Subject to floor rate and may require the automatic payments be made from a checking or savings account with the lender. The rate reduction will be removed and the rate will be increased by 0.25% upon any cancellation or failed collection attempt of the automatic payment and will be suspended during any period of deferment or forbearance. As a result, during the forbearance or suspension period, and/or if the automatic payment is canceled, any increase will take the form of higher payments. The lowest advertised variable APR is only available for loan terms of  5 years and is reserved for applicants with FICO scores of at least 810.

As of 12/019/2019 student loan refinancing rates range from 1.90% to 8.59% Variable APR with AutoPay and 3.49% to 7.75% Fixed APR with AutoPay.

1.99% – 6.89%1Undergrad
& Graduate

Visit Earnest

2.31% – 7.36%2Undergrad
& Graduate

Visit SoFi

2.06% – 6.81%3Undergrad
& Graduate

Visit Figure

2.62% – 6.12%4Undergrad
& Graduate

Visit College Ave

1.99% – 6.65%5Undergrad
& Graduate

Visit Laurel Road

1.99% – 7.06%6Undergrad
& Graduate

Visit Splash

1.85% – 6.13%7Undergrad
& Graduate

Visit CommonBond

1.90% – 8.59%8Undergrad
& Graduate

Visit Lendkey

Our team at Student Loan Hero works hard to find and recommend products and services that we believe are of high quality. 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 to help you understand what you are buying. Be sure to consult with 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.

Published in Career & Jobs, Success Stories