Insights & Advice from 3 Women Who Work for Themselves

Before I cannon-ball into some very expansive and uplifting tales of women who left their traditional 9-5 jobs to venture out on their own, I want to offer up one Corporate America-sized disclaimer:

I am not encouraging anyone to quit their jobs.

Read it. Underline it! Read it again. Honestly, I think it’s so fashionable to complain about working for #TheMan that sometime we do it just to join the chorus – there’s nothing wrong with liking your full-time job; in fact, I recommend it!

But I know there are a lot of people out there who aren’t happy at work, but aren’t really sure what to do about it. Today, I’ll spotlight some beautiful insights from women who left their traditional employment to work for themselves.

Another reason I’m thrilled to spotlight these women (and why I think their stories are so eye-opening) is because they quit their jobs and went full-time freelance/entrepreneurship in early 2020, when so many of us were clinging to our current situations with fear and uncertainty.

All that to say: It was possible. It is possible.

The women

• Susie, a 25-year-old who went from teaching at a public high school to running her own freelance copywriting business

  • Old income: $55,000 annual salary before taxes

  • New income: $48,000 – $60,000 annually before taxes (based on an average of $4,000 to $5,000 per month)

• Jen, who went from working at a product marketing firm to running her own marketing firm

  • Old income: $52,500 annual salary before taxes

  • New income: $180,000 – $300,000 annually before taxes (based on an average of $90,000 to $150,000 every six months, dependent on the programs she launches)

• Leslie, a 31-year-old pharmacist who went from working as a pharmacy manager to pharmacy contracting/consulting

  • Old income: $138,500 annual salary before taxes

  • New income: $132,000 annually before taxes

These three have an abundance of goodness to share with you – from unexpected things that worked in their favor (and things that you might assume at first glance are unfortunate!) to deeper learnings about happiness and fulfillment.

While I’m tempted to go the lazy route and copy/paste everything they sent me, I’ll honor the editorial integrity of this site and instead distill down their answers to the big-picture insights – things that I think everyone (me, a full-time employee of a huge corporation, included) can learn from and be inspired by.

How they knew it was time to go

At first glance, I think it’s obvious that Jen’s income changed pretty dramatically — she sextupled it, which is an erotic way to say she multiplied it by 6. I think multiplying your income by 6 is, in fact, pretty sexy.

I asked all three women the same questions, and I want to share her answer when I asked her to tell me about her side hustle and what convinced her to make the leap:

“My side hustle was an escape from my corporate job. To be completely honest, the environment I worked in was toxic and was taking a toll on my mental health. I was eager to take on bigger projects, but there was little opportunity to do so. I felt stuck and wanted a way out, so NEAT Marketing was born in September 2019. I didn’t leave my job until the end of December, so I had a few months to grow my company and start on client projects. I wanted to build up my savings a bit before taking the leap. 

I got my MBA in 2016, intending to start my own business (eventually). I felt that in order to take the leap, I needed years and years of corporate experience or no one would take me seriously as a business owner. I’ve always been ambitious, independent and stubborn, making it hard for me to take orders from a manager.

I was truly never cut out to be chained to a desk and work 9-5 building someone else’s empire – it just took me YEARS to come to this conclusion. The moment that finally caused me to start my business was this:

Six months into my corporate job, I had finally saved up enough PTO to go home and see my family for the first time since Christmas 2018. When I landed in my hometown and turned on my phone, I had a dozen missed calls and angry texts from my boss and our VP. They needed a project finished ASAP, so I had to work for 9 hours that day, instead of spending time with my family. I didn’t even get a simple “thank you” from my boss, or VP, for completing this project.

I thought to myself, “This can’t be it for me. There has to be more out there.” So that’s when I decided to start my company! I knew it was going to come to a point where balancing a side hustle with a corporate job wasn’t going to work, because there are only so many hours in a day. So I decided to go all in starting in January 2020. It was the best decision I’ve ever made.”

I’m praise-hands-ing all over the place right now. My initial reaction to this was, holy shit, I can’t imagine anyone at work treating me this way, so no wonder Jen was 50 shades of ready to bounce.

A few things about her story I want to highlight:

So often when we discuss the notion of leaving a “safe” job for the unknown, we treat it as though it’s just a matter of courage.

As if starting a company comes down to nothing more than the willingness to quit your job.

But Jen had an MBA. She had years of experience (although not a TON, to be sure). She was qualified, but she didn’t stick around too long. After three months of building up clients, she saw the financial viability and plunged.

Leslie made a point I’d also love to include here when asked about why she decided it was time to go:

“I realized I needed to make the jump when the money and benefits no longer made up for the nights/weekends/holidays/sanity that I was lacking. I wasn’t allowed an off-switch. An email or important call at midnight? I had to be there. I was always on GO, and it just wasn’t sustainable, nor was it a fulfilling life. I went through a major life event in 2015/2016 that made me reevaluate all priorities and being at the top of the ladder by myself just wasn’t one.”

I wish you could’ve heard my audible, emphatic “mph!” in response to “and being at the top of the ladder by myself just wasn’t one.”

Y’all remember her income before, right? $138,000? I feel like I’d probably put up with a whole lot of bullshit for $138,000, but imagine reaching a point where you’re so driven into the ground that even $11,000 per month isn’t enough to make you want to stick around.

And of course, it doesn’t have to be one mind-blowingly shitty experience or the culmination of a lot of stress – sometimes, you just know it isn’t for you. Enter: Susie.

“While I realize that this is incredibly privileged as millions of people around America have had a terrible time during the pandemic, the drop in in-person teaching allowed me to build my business and realize that I was about 1,040X happier writing than I was spending all day in a classroom.

I knew that if I went back to school, I wouldn’t be able to continue building my business, and that I would be wildly unhappy doing a job that just… wasn’t for me. I talked myself in and out of it multiple times (my poor mom and friends were probably like… just MAKE UP YOUR MIND), and I knew that I would continue to noodle back in and out unless I sent in a resignation letter and forced myself out. No regrets.”

I love two things about this.

For one, you’re allowed to find silver linings and benefit from an overall shitty situation. Just because we’re in the midst of a political meltdown, global pandemic, hurricane season, and months of wildfires doesn’t mean you can’t still find some joy and success, honey! I love that she called it out. You’re allowed to realize you’re happier now. Maybe that’s a clue.

Secondly, I love that she highlighted how she was waffling. Often times big decisions aren’t going to feel 100% clear in the moment, especially when they result in a huge shift.

I want to hammer home that all three of them had a plan and savings – they had already proven out their ability to create substantial income from their side hustles and they had saved a small fall-back fund just in case things went awry. While this whole topic feels so free-spirited and “jump if you dare!”, I think it’s important to note that there was a methodical and risk-avoidant strategy taken in all three cases. There was a plan.

In other words, we can’t overlook the importance of the financial viability of whatever you’re going to do in your post-work era.

The surprising side effects of working for yourself

I was interested to hear if there were any ostensible downsides to this way of life they’re all pretty sold on, since I can think of a few right off the bat.

Since Susie plugged my overall mantra in her answer, she’s up to bat first. Bribery works, people!

“The best moment has been realizing that I’ve finally started to create a life for myself that gives me freedom and joy and space to make my own decisions. The worst is 10000000% taxes. For sure, taxes. Ew. Gross. The worst. Also… why is creating a business account such a massive pain in the ass? What’s also surprised me is that I’m strangely feeling more freedom around money than I have in quite a while. I’m not sure if I’m more cognizant of the fact that it’s not coming in on the same day of each month or not, but I’ve felt much less compelled with impulse purchases while also feeling much more relaxed about the general state of my bank account.

Also, in true KG form, turning all of my savings/bills into AutoPay has really chilled me out. When I was teaching, I would pay everything on the same day every month… and then be stressed during the month, using all of my writing income as ~whatever I want~ type of money. Now, I know that things come in when they come in, I’m prioritizing saving, and feeling generally relaxed.”

You may have noticed above in the income breakdown, but Susie’s income actually is still pretty similar before- and after-the-leap – so I think it’s fascinating that she feels more relaxed about it. It’s a case for value being a slippery property: The money she got from a salary at a job she didn’t love felt less valuable than that which comes from her writing business.

Leslie also noted that taxes are the worst part, so there’s something to consider there. If you think your W2 taxes are a pain… sounds like things get hairy when you stamp your passport to 1099 land.

Jen’s take will probably feel refreshing as well, especially for those of you like me who, at some point, were brainwashed by the Gary Vee “If you aren’t working 20 hours a day, you don’t want it badly enough” mindset:

“I always thought entrepreneurship was about the grind – working hard and working for long hours – and that has not been the case at all. The saying, “work smarter, not harder” is so true. Hiring a team to help me with the day-to-day tasks has really allowed me to step into a CEO role, stay within my zone of genius and focus my time and energy on money-making activities. I know without my team, I’d be working nonstop!

Another thing that has surprised me: People who I thought were my best friends turned out to be… not the most supportive of my new venture. I constantly got comments like, “Well what are you going to do for money?” and, “I don’t really understand why you would take a risk like this when most new businesses fail within the first year.” I’ve said goodbye to a lot of friendships that were no longer serving me.

When you go full-time in your business, it’s really important to surround yourself with people who believe in you. The best moment to date has been hitting my first six figures! As for the worst, a few months ago I had to let go of a contractor I really liked (as a person), but she just wasn’t doing her job and I didn’t know where my money was going. It was such an uncomfortable conversation for me to have.”

A few things I’m taking from this:

• My inclination to work smarter (not harder) has been right all along.

• Support is crucial – and that goes both ways. Support your friends. It’s not your job (I’m mostly telling myself this) to list all the possible terrible outcomes of their business venture. They probably already know! Belief goes a really long way.

Leslie put the “best” thing about being an entrepreneur pretty perfectly:

“The best moment? Probably every day when I get to wake up and decide how I want my day to go instead of someone else dictating that for me.”

Oof. Yep. Sounds pretty glorious.

How their self-perception has been altered

Arguably the most meaningful reason people pursue their own projects is because they feel otherwise unfulfilled.

Ideally, the money is the happy consequence, and the true driving force is something that runs deeper. When I asked these women how their sense of self has changed, they had interesting answers:

“I’ve realized that I trust myself for a reason. I spent the last 3 years of my life being overworked and overtired, and that’s gone—more so replaced with the realization that I’m right where I’m supposed to be, and that’s so freakin’ worth it.” – Susie

and:

“When I first started my business, it was a side hustle and I wasn’t sure if it would ever be able to replace my corporate salary. I was really lacking confidence in myself in the beginning of this journey and even had thoughts about going back to corporate. I was overly concerned about what my peers thought of me and was afraid that I would be judged if I failed!

But, as I signed more and more clients, hired a team and scaled my business… I started to feel like a leader, a real CEO. I finally realized that I was never meant to play small. Corporate would have been the safest route for me to take but I’m SO glad I left. I’m a corporate dropout turned 6-figure marketing + sales coach. A year ago, if you would have told me this is where I’d be, I would have laughed. I feel successful and like I’m making a difference. I get paid to help my clients grow their brands and make more money – how cool is that?! Sometime I feel like I’m living in a dream.” – Jen

I feel like I’m at a Tony Robbins conference. I’m not going to lie – I read this one and almost immediately hit reply and was like, I need to hear more from you, because I, too, feel like I’m reading someone describe a dream.

Finally,

“I am incredibly proud of myself. I have realized that I am a lot braver to face the unknowns than others. This was portrayed to me in the past as being irresponsible, and that feeling made me question every move. A lot of wisdom and growth helped me understand that staying in a career path for the sake of financial safety at the cost of my well-being and relationships was a bigger irresponsibility to my future self.

Since switching to consulting, I have the most incredible sense of freedom. I am no longer constantly trying to get a seat at the “Good Ole’ Boys Club” to have a voice. It’s a huge responsibility (that can feel daunting some days) that what I do depends on me only, but it’s freeing in the best way. I make my schedule around my own life events, vacations, etc. This doesn’t mean I lay by the pool every day or that I don’t still work 40-hour work weeks, but it does look different. I am a better friend, wife, sister, etc. because I have more in my cup to give.” – Leslie

What it all comes down to

I know y’all have short attention spans so if you made it this far, I’m proud of you. For better or worse, I’ve always been the type who needs to distill everything she encounters in life into actionable, meaningful takeaways. Let’s do this:

• It’s possible, even though majority of your friends and family will probably discourage you (out of love and protection). But you know what? All you need to cling to here is possibility. Let that expand your frame of reference for what’s doable.

• Financial viability matters. A lot. There’s nothing stress-free and empowering about quitting your job to twiddle your thumbs and wonder how you’re going to make your first $100. These women had a strong proof-of-concept before leaping, and were essentially working two jobs for months before deciding Job #2 could pay the bills on its own.

• Some people aren’t meant to work for someone else, and it’ll never be how they get the best out of themselves. Some people are. There’s nothing wrong with preferring the stability and certainty of a corporate job, but be careful not to hyperbolize “stability and certainty” – as we’ve seen in 2020, sometimes the “sure thing” path isn’t sure after all.

• You’re never stuck, and because you’re never stuck, you never need to stress too much about a bad situation. That’s my biggest takeaway. While it often feels like jobs are scarce and money is hard to come by (because that’s the narrative we’ve all agreed upon), I point you to these three examples of women who took their skill sets and monetized them to replace or surpass their old incomes from gigs that were making them actively unhappy.

How do we feel about focusing more on side hustles? Yes? No? Boss me around. I’d love to hear what you think of this, so send me a DM or email.