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

Taking a leap from working for a company to self-employment is not easy, but if you're thinking about doing it, you'll be among many other ambitious women. According to Forbes, self-employment rates went up among us post-pandemic. Women represent at least 40 percent of all self-employed professionals, an increase from 34 percent in 2016.
According to other research, among women-owned businesses, 90 percent have no employees. Ninety-six percent of Black-owned businesses, overall, have no employees. Self-employment has also been deemed an “essential part of the economic stability of mothers,” with women launching their own sole proprietorships and side hustles (or freelancing their skills to brands and companies) in order to have time and earnings flexibility.
Women left their jobs in droves during the Great Resignation, and although some have returned to work, many, like myself, are still riding self-employment until the wheels fall off. Leaving a stable job with benefits to go off on your own, you might be thinking, "Well, how will I pay my bills? I've got a lifestyle to uphold."
Here's what has helped me and many others in planning to make an exit from a 9-to-5 to pursue dreams of working for ourselves:
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.
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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.
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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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'Sistas' Star Skyh Black On The Power Of Hypnotherapy & Emotional Vulnerability For Men
In this insightful episode of the xoMAN podcast, host Kiara Walker talked with Sistas star Skyh Black, as he opened up about his journey of emotional growth, resilience, and self-discovery. The episode touches on emotional availability, self-worth, masculinity, and the importance of therapy in overcoming personal struggles.
Skyh Black on Emotional Availability & Love
On Emotional Availability & Vulnerability
“My wife and I wouldn't be where we are today if both of us weren't emotionally available,” he shared about his wife and Sistas co-star KJ Smith, highlighting the value of vulnerability and emotional openness in a relationship. His approach to masculinity stands in contrast to the traditional, stoic ideals. Skyh is not afraid to embrace softness as part of his emotional expression.
On Overcoming Self-Doubt & Worthiness Issues
Skyh reflected on the self-doubt and worthiness issues that he struggled with, especially early in his career. He opens up about his time in Los Angeles, living what he calls the “LA struggle story”—in a one-bedroom with three roommates—and being homeless three times over the span of 16 years. “I always had this self-sabotaging thought process,” Skyh said. “For me, I feel therapy is essential, period. I have a regular therapist and I go to a hypnotherapist.”
How Therapy Helped Him Heal From Self-Doubt
On Hypnotherapy & Empowering Self-Acceptance
Skyh’s journey is a testament to the power of tapping into self-development despite life’s struggles and being open to growth. “I had to submit to the fact that God was doing good in my life, and that I'm worthy of it. I had a worthiness issue and I did not realize that. So, that’s what the hypnotherapy did. It brought me back to the core. What is wrong so that I can fix it?”
Watch the full podcast episode below:
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Women Are (Still) Spelling 'Coconut' With Their Hips. And Guys Are Losing Their Damn Minds.
While prepping for a podcast interview a while back, because I received the questions beforehand, I did a bit of research into one of the inquiries: what are men’s current favorite sex positions? I doubt any of you are shocked by the fact that what continued to pop up (like here, here, and here) was doggy style and the cowgirl position (i.e., when a woman is on top).
When it comes to ridin’, specifically, that got me to thinking about something that was all over the internet a few years ago: women who were advising that you spell “coconut” with your hips, during sex, in order for you and your partner to receive maximum pleasure and satisfaction.
When I asked a few women I know if they ever tried that before, I was surprised to discover that not only had they, but many didn’t treat it as some random social media fad — they actually still do it to this day. Partly, because it’s fun to them and partly because their partner(s) seem to go crazy for it.
Listen, any time something sexual works like a charm, I’m going to shout it out — (late) trend or not. And so, if you’ve never heard of the whole coconut thing, you tried it and forgot all about it, or you just want to try something new/different/else tonight — here’s a reminder, in article form, that coconut-ting is still alive and well, y’all. And the men are all about it!
But First, The Grapefruit Technique
Video Credit: Myem/YouTube (Funny part starts at 2:40)
If this woman is not familiar to you on sight, you ain’t a real one. LOL. Although I know that a lot of people think that the concept of grapefruiting came from the movie Girls Trip (you can see the clip from the film here) that absolutely is not the case. Auntie Angel (whose real name is reportedly Denise Walker) is the creator of the Grapefruit Technique and although I thought that this video came out way earlier, apparently it made its way onto the YouTube streets sometime back in 2014.
If for some reason, you’re not familiar with grapefruiting on any level, I will tell you right now that I had to download this video because it is absolutely NSFW — so you should probably watch it on your lunch break (on your phone with the volume as low as possible) or at home…because chile, the sound effects? Whew, the sound effects. LOL. However, when I sat down to pen this piece, I thought it was hilarious that this video is what immediately came to mind because it seems like, when it comes to “blow his mind sex hacks,” fruit is constantly on the menu.
When it comes to oral sex, it’s grapefruit.
When it comes to ride ‘em cowgirl, it’s a coconut.
What Is the “Coconut” Sex Trend?
@windy_moraba #duet with @mysteri0us.gir1 spell coconut with your waist 😂😂😂
Okay, so what in the world does a coconut have to do with intercourse? Well, for starters, if you and your partner are looking for an all-natural lubricant, coconut oil works well. HOWEVER, do keep in mind that the disclaimer on this is you shouldn’t use it if condoms are in the mix because they can actually cause rubbers to be less effective (silicone lube is a solid bet for condoms, by the way).
There is another way that coconuts are kinda-sorta incorporated when it comes to making sex more pleasurable — and it actually became pretty popular right after COVID lockdown (2021): spelling C-O-C-O-N-U-T with your hips while you’re on top of your partner.
It’s wild how I forgot all about this until a client of mine was telling me how much her husband liked her on top while it wasn’t her favorite thing to do because it felt awkward to her. When I said, “Have you ever heard of spelling ‘coconut’ with your hips before?” — at first, she looked at me like I was crazy and then she busted out laughing: “Girl, no” was her reply.
Hmph. Don’t knock it until you’ve tried it because, as wild as it might sound on the surface, the word isn’t the point so much as the movements that come with spelling it out are.
When you’re moving your pelvis around to make a “c,” “o” or U-turn, not only does it intensify the level of sensation that both you and your partner feel during intercourse, it can also increase the level of blood circulation to both of your genitalia which can make your orgasms more satisfying too.
At the end of the day, spelling “coconut” is simply reminding you that there are more options to riding than simply sitting there while your partner pumps for all he’s worth or you humping up and down like you’re on a pogo stick.
Spelling “coconut” is an easy hack to bring some variety into cowgirling. However…
Honestly, the “Fruit” Isn’t the Point. THIS IS.
From grapefruiting and spelling “coconut” to reading articles that I’ve penned for the platform like “How To Improve The Taste Of Sperm” — fruit and sex are always going to be a winning combination, one way or another. However, the main point of this article isn’t about making sure that you are a master speller so much as providing you with tips that will make the cowgirl position something that you are confident about and you find a ton of fulfillment in doing.
You can make both of these things happen by incorporating the following things:
Stretch beforehand. A charley horse during sex is the worst thing ever — and chile, don’t let it be right before you’re about to climax. SMDH. Yeah, if you want to feel more comfortable when you’re on top, make sure that you stretch beforehand and that you are well-hydrated. That will reduce the chances of experiencing a totally-out-of-nowhere muscle spasm — whether you decide to “spell” during sex or…not.
Bring pillows into the mix. Sometimes riding is a challenge because your partner feels farther away from your body than you would like. Putting a pillow underneath him can help to elevate his pelvis, so that you don’t feel like you’re stretching and straining. Speaking of pillows, a longer one can really come in handy because it can give your knees some additional support as well.
Also, ask him to put his knees up. Speaking of making the “grind” easier for you, ask your partner to put his knees up. That way, your back can recline on his legs as you’re moving your hips around. You’d be amazed how much this one hack can do for you. Straight up.
Add lube. When you get a chance, check out “The Wetter, The Better: 10 Creative Ways To Use Lubricant” and you will automatically see why bringing lubrication into a cowgirl session is an absolute must. It reduces friction. It makes your movements glide with ease. And it’s just more fun. Promise you that.
Lean in. If your partner happens to be on the larger side of life, one way that you can control his depth is by leaning forward into him. That way, your hips can better control how much or little he is inside of you, so that you can get into a position that gives you the sensation that you are looking for.
Get him to multitask. Again, whether you are spelling “coconut” or not and whether you are riding cowgirl or reverse cowgirl — something that is awesome about being on top is it frees your partner’s hands to do, umm, other things. And since it is so much easier to have an orgasm while your clitoris is being stimulated, get your partner to put some of the lube that we discussed earlier on his fingertips, so that he can gently rub on your clitoris while you are riding him. It doesn’t get much better than that!
Don’t wanna spell? Hula Hoop then. What if you try the whole coconut thing and it’s not a favorite for you (or him)? No problem — when’s the last time that you hula hooped? Pretend that you have one of those around your hips and move around that way. I’d be shocked if you ended up feeling “meh” about that option.
5 Guys Tell Me What They Love When Their Partner Is on Top
A part of the reason why I am “team cowgirl” is because it provides a lot of benefits to the woman: she has more control, it tends to be more comfortable for her, it’s a great position for a quickie and the orgasms tend to be that much more — wonderful. However, as I was thinking about spelling coconut, in general, I couldn’t help but wonder what guys thought about it and the cowgirl position overall.
If you’re curious, here’s what five of ‘em said.
1. Braxford. Engaged. 35. “Y’all be spelling up there? Who knew? My favorite thing about when my fiancée is on top is what I think every man likes: the view. It’s a chance to see her entire body and experience it at the same time. Not even doggy style accomplishes that. Damn, where’s my lady at?”
2. Denez. Single. 42. “Do you know how many ‘spots’ you have access to when y’all are on top? Breasts are in my mouth. Hickeys are on her neck. Prop my head up on a pillow and her tummy is getting licked. When a woman is riding you, it’s sensory overload! It’s crazy how each one looks amazing in that position too.”
3. Omar. In a Serious Relationship. 29. “[He said her name yet I’m not going to share it] isn’t a very vocal lover. Her body and technique are insane, so even though I love dirty talk, I’ve learned to compromise — except when she’s on top. She’s not saying much but those moans? And yeah, we tried the coconut thing. ‘Cs’ and ‘Os,’ hell yeah. ‘Ns’ and “Ts’? Nah.”
4. Nolen. Single. 45. “45 isn’t old but it’s old enough for your back to show out on you when you least expect it. My experience has been that women don’t want a lot of thrusting when they are on top, so it’s like having some of the best sex without having to do much at all. Well, aside from trying not to bust too quickly. I take that back: riding is easy on the body; it’s work on the brain.”
5. Ivan. Married. 37. “I like the spelling sh-t because it switches things up. We make a game out of it by her picking a word and spelling out while I try and guess what it is. We also try to see how many words that we can get to before one of us cums. 12 words is pushing it unless it’s like ‘dog’ or ‘cat’ or something. I’ve guessed ‘coconut’ a few times and I get what the excitement is all about. Spelling bee sex: try it.”
Yep. I concur.
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