From 9-To-5 To Self-Made: How To Transition Into Self-Employment Without Going Broke

1. Tighten up that spending and map out an adjusted budget for your future self-employment life.

This is almost like budgeting backward. Think about what you'd like your life to look like once you've gone off on your own, and figure out a ballpark figure of how much that lifestyle will cost. Be sure to note the non-negotiables first (like childcare, housing, food, education, social life, church, and other expenses already part of your budget that you refuse to compromise on).

Get clear on why you're pursuing self-employment in the first place (i.e., to travel full-time, downsize in order to live simpler, focus on mental health, prioritize stay-at-home parenting, or retire early) and what lifestyle aspects might change because of your choice.

This will help inform the budget you put together that will prompt actions to lead to your tomorrow, not those that are sustaining you today.

Do you need to fast from Amazon purchases for six months to a year in order to save up? Do you need to purchase more insurance policies? Do you need to set aside funds to invest in a website or get more training in order to step fully into self-employment? Do you need to move to a smaller home, get a roommate, or decline more than a few happy hours in order to have enough money to feel confident in leaving your job?

2. Set a number and a deadline for when you'll resign so that you can follow a deliberate savings plan to reach a specific goal.

If you want to have a certain quality of life once self-employed, figure out that dream number and then work toward achieving that (or at least build habits that will get you to that number once you're self-employed for good.)

And set a deadline for leaving in order to plan savings accordingly. For example, if I were working a 9-to-5 and needed $20,000 in order to feel secure enough to quit my job (with the consideration that I might possibly be without steady income for the first six months and need to cover basic bills during that time), I'd need to save up little over $3,300 a month for six months in order to do that.

You can break down the cost in months, weeks, or years, depending on your deadline, timeline to resign, and financial obligations you'll still need to cover once you quit your job.

3. Talk with a financial adviser, bank rep, or accountant to help you crunch some numbers.

If you find the thought of leaving a job and going the self-employed route stressful when it comes to financially planning the shift, get some help. Many credit unions and banks offer resources and professionals who can let you know what shifts you might need to make financially or give you a real sense of how you're already spending money so that you can adjust your budget to save and plan financially for your new future.

Be sure if you go with an accountant that they're certified and that they have experience working with entrepreneurs or self-employed professionals. They might also be able to suggest ballpark figures for changes in taxes and interest rates that might need to be considered (or at least lead you into thinking about those things so you can take your questions to a tax expert). ​

Get the help you need so that you can arm yourself with information to fight fear and really take the action you need to set yourself up financially to transition into self-employment.

4. Use spreadsheets and other tech tools to help you track your plan and allow you to easily see the progress you're making in saving up and prepping for self-employment.

Sometimes spreadsheets can seem a bit complicated and annoying to use, but if you're good at creating and using them, please do. If you're not, there are templates you can use for budgeting that are perfect for setting up your "Quit My Job And Go Self-Employed" budget. You'll want to think about how much you can reasonably save, plus other ways to cut costs that won't drastically impact your quality of life, work output, or mental health.

If your bank has an app that tracks your spending and allows for organizing the information to track it, use that feature. You can also use budgeting apps to track your spending, offer reminders, or alert you of limits you've set so you can reach certain goals.​

5. Start landing contracts and clients while you're employed.

It might not be ideal to fast-track your quit date if you don't have savings or some other form of financial help, but if the pressure will motivate you, by all means, put things into high gear. I had very little savings when I left a job to go self-employed, and thank God it worked out, but I've learned through the years that the transition would have been a lot easier had I saved a bit more before resigning. I literally could have stayed an extra nine months to a year, gotten more clients and experience, and been a bit less stressed in my self-employment transition.

Even if your plan is two years from now, within those two years, you should be building up a framework that allows you to make more money today. Network, build that website, start offering your skills on a freelance basis as a side hustle, and funnel that money into savings for your future when you're fully self-employed. Talk to someone about investing some of those savings so that they can grow.

As long as what you're doing on the side is in alignment with any employment contracts and policies and does not jeopardize your standing at your day job, you can start squirreling money you're earning today doing what you will one day leave your job to do full time.

When I left my job years ago, I got my first client through a referral from someone I knew in my industry. My next one was also a referral---someone I'd worked with while being employed full-time at a company. By the time my little savings had run out, I'd already landed contracted work that guaranteed a certain amount of money, covering my bills through a certain period of time.

From there, I planned accordingly in order to increase my earnings, adding in clauses and other amendments in contracts to protect myself financially.

Transitioning into self-employment doesn't look the same financially for everyone, and some of us have to make real sacrifices in order to build up to the future life we want. For me, that included radically cutting out a few things I loved, leaving an apartment and going fully digital nomad, and maybe even taking on a few odd jobs in order to add to my savings in order to quit.

For you, it might look like cashing out that 401K (I did that, too, but beware of the penalties, as this should really be a last resort option.) For others, it might be using that "new car fund" to fund your life while you're working to land new clients from a beach paradise somewhere or living the exact same quality of life you had at your 9-to-5 because you were great with your savings, have help in the form of a spouse, or come into a cash settlement or inheritance.

However it looks for you, be smart with what you have, think positively and strategically about how you can realistically finance your transition, and utilize an exit plan that makes the transition much easier.

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