Get the 200+ Page Optimal Living Daily Workbook (PDF) - Free.
Want to turn today's episode into an actionable plan? Join the Optimal Living Weekly newsletter and I'll send you our 200-page digital workbook immediately. It's packed with the best takeaways from the show, formatted for easy reading and implementation at home.
Get your free PDF workbook here: https://oldpodcast.eo.page/join
Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com
Episode 2214:
Michelle Schroeder-Gardner explains how to prepare to quit a day job and become self-employed, drawing on her own move to working for herself full-time. In this first part, she makes the case for building a business on the side first, which lowers the risk while testing whether the idea can actually replace a full-time income. She also walks through pricing out health insurance and the other benefits an employer used to cover, so the switch to entrepreneurship brings fewer surprises.
Read along with the original article here: https://www.makingsenseofcents.com/2022/01/how-to-quit-your-job-and-become-self-employed.html
Quotes to ponder:
"Starting your business on the side of your full-time job can reduce a lot of stress."
"Self-employment isn't for everyone."
"It's much better to do your research and price out how much things like health and dental insurance will cost before you quit your job."
Optimal Work Daily is a daily career advice podcast where we narrate the best articles on productivity, entrepreneurship, and work-life balance, read to you by a professional narrator so you can grow your career a little more every day.
Learn more about your ad choices. Visit megaphone.fm/adchoices
[00:00:00] Observe. The North American Dad. 50s. Great Polo Collection. He enters his vehicle information on Carvana. An offer appears in minutes. Remarkable. He squints, reads it again, smiles and says, dang, that's a good offer. The highest form of approval. No haggling. No hassle. No one called him boss. He's still on the couch. Astonishing. Sell your car today on Carvana.com. Pickup fees may apply.
[00:00:30] UKG is the workforce operating platform with unified HR, payroll and workforce management. Built to solve the unique challenges of frontline work. Powered by People First AI and decades of labor data, UKG turns workforce intelligence into real-time decisions around staffing, pay, compliance and productivity. Enabling every worker to confidently take action as work happens. Because when work works, everything works. Learn more at ukg.com slash work. UKG. HR, pay and workforce management.
[00:01:00] This is Optimal Work Daily. How to quit your job and become self-employed. 5 Steps for Success, Part 1 by Michelle Schroeder Gardner of MakingSenseofSense.com. Do you want to learn how to quit your job and become self-employed? Whatever reason you may have, I recommend taking some steps so that you can prepare and make the transition to self-employment as easy as possible. I've been self-employed for around 8 years now, and there were several things I did to prepare for the switch.
[00:01:28] I was a little scared to leave my day job in order to work for myself full-time, and preparing helped me with the transition and made me feel more comfortable. Of course, not everyone has the opportunity to prepare for self-employment, as I know that some people may be laid off from their day job, or maybe you have to quit a toxic work environment, and so on. But anything that you can do to prepare will make the switch as easy as possible. Learning how to quit your job and become self-employed is hard work, and there are a lot of steps a person needs to take before they think about leaving their current job.
[00:01:58] Even though I'm going to walk you through steps that will teach you how to prepare to quit your day job and work for yourself, there's no single right way to do it. Depending on your situation, you may take slightly different steps. That's okay, and you'll have to find out exactly what works for you. However, by taking your time to become self-employed and preparing yourself, you may have a much smoother transition. How to quit your job and become self-employed Step 1. Create your business on the side of your day job
[00:02:26] Perhaps you've finally found your passion, and it means running your own business. Maybe your side hustle has grown so large that it's time to make a decision between keeping your day job or turning your side hustle into your full-time career. If you have the option, I highly recommend starting your business on the side of your day job. This is because you'll still be able to rely on the income from your day job, meaning there is less risk if your business doesn't turn out to be what you thought it would be. Starting your business on the side will allow you to see if it's 1. Something you want to do full-time.
[00:02:56] Is this a business idea you'll actually like once you've started it? Self-employment isn't for everyone. 2. A realistic way to make an income. Will you be able to live on your business income alone? And 3. A business that will work out or not. Is this a business idea that will succeed? Starting your business on the side of your full-time job can reduce a lot of stress. You'll be able to build up your business to the point that you're earning good money before dropping your stable full-time income.
[00:03:23] For me, I had my business on the side for around 2 years before I decided to make the leap into self-employment. There is no right or wrong amount of time for each person, just what you think is good for you. 2 years may be too long for some people, and it may not be long enough for others. Like I said, there's no set amount of time. Step 2. Determine what you'll do without your day job benefits. One of the major perks of full-time employment are the benefits. Full-time benefits are something many people rely on,
[00:03:51] and you will most likely lose them when you start working for yourself full-time. I know many people struggle to leave their day job because the benefits are so valuable. When you quit your day job, it will be your responsibility to take care of health insurance, retirement, and so on. It's much better to do your research and price out how much things like health and dental insurance will cost before you quit your job. This will give you a much better idea of what your self-employment budget will be. After all, your expenses may be a little higher than what they are now,
[00:04:20] so this helps to eliminate any surprises that you may come across. Health insurance is probably the biggest hurdle for self-employed people. However, there are some options you may want to explore. Including 1. Find an insurance plan on the marketplace at healthcare.gov 2. Find travel medical insurance 3. Joining a health share These are not a perfect solution as they are not required to pay for your medical bills. 4. See if you can use COBRA for a short time frame
[00:04:47] This is where an insurance company is required to give you insurance even after you leave your day job. But it can be very pricey. 5. If you have a partner who has a job with health insurance, you can see if you can join their health insurance plan. 6. If you belong to a professional group or association for the industry you're in, they sometimes offer health insurance options for their members. All of these options will have pros and cons, and not all of the options will make sense for you.
[00:05:13] Take time exploring each one, from how much it costs to if there are any restrictions for the type of care, before deciding which is best for you. If you want to learn how to quit your job and become self-employed, taking your time to research benefits is a very important step. And unfortunately, health insurance is a hard topic that doesn't have a single easy solution for everyone. Step 3. Hear that on tomorrow's episode.
[00:05:41] You just listened to part one of the post titled, How to Quit Your Job and Become Self-Employed, Five Steps for Success, by Michelle Schroeder-Gardner of makingsenseofsense.com You're listening to a quick ad. You know what else is quick? Selling your car on Carvana. Just put in your vehicle information and we'll give you an offer. Done. No hassle. No negotiation. No guy from an online listing lowballing you. Which means, by the time I'm done explaining this, you could have basically done it.
[00:06:15] Still haven't started? Hey, better late than never. Sell your car today on Carvana. Pickup fees may apply. UKG is the workforce operating platform with unified HR, payroll, and workforce management. Built to solve the unique challenges of frontline work. Powered by People First AI and decades of labor data, UKG turns workforce intelligence into real-time decisions around staffing, pay, compliance, and productivity. Enabling every worker to confidently take action as work happens.
[00:06:43] Because when work works, everything works. Learn more at ukg.com slash work. UKG. HR, pay, and workforce management. And as always, I want to thank Michelle, one of our regular contributors, for sharing this post. She created Making Sense of Sense to keep track of her own financial progress, help readers improve their finances, and help her own personal finances. As an example, due to this, she was able to pay off $38,000 in student loans in just seven months.
[00:07:11] And like many of the authors on our shows, Michelle went from being in debt to being financially free. Man, you can follow the journey yourself because she has documented the entire journey right there on her blog. She's pretty open about it, so you can check all of that out. And again, her site is Making Sense of Sense, C-E-N-T-S dot com. Okay, that's going to do it for part one. And come on back tomorrow for the Saturday show because that's where we're going to wrap up part two of this post. And it's where your optimal life awaits.

![2214: [Part 1] How To Quit Your Job And Become Self-Employed - 5 Steps For Success by Michelle Schroeder-Gardner on Starting A Business](https://images.beamly.com/fetch/https%3A%2F%2Fmegaphone.imgix.net%2Fpodcasts%2F1c9d43ce-b211-11f1-89cd-433795652c77%2Fimage%2F82d6e6ea8a0b60c2c3699e3d29e588d9.jpg%3Fixlib%3Drails-4.3.1%26max-w%3D3000%26max-h%3D3000%26fit%3Dcrop%26auto%3Dformat%2Ccompress?w=365)


