How To Be Your Own Boss And Stick It To The Man

Sometimes you find yourself enduring the consequences of your own shit decisions. And then there are times you find yourself inexplicably lumbered with the consequences of someone else’s. Never is this clearer than when you’re thrown out into the working world at the tender age of sixteen, eighteen, or twenty-one, or whenever you finish your education or need to work to pay for your education. 

My early working career was…bumpy. Bar work and later working for my university got me through my degrees, but once I was done with my Masters and applying for PhD funding, I needed full-time work. As a trained archaeologist, I naturally looked for work in my field (no pun intended). I found nothing to be had up north until I had at least six months of professional experience working for an archaeology unit. So I packed up my stuff, moved down south, and took a job at the only archaeology unit willing to take people without that experience.

I rapidly learned the reason they had that policy; it was a terrible place to work, and anyone with other experience wouldn’t put up with that shit.

But I was young and naive and didn’t know that yet. 

So when the pressure of long distance ended my relationship, and I found myself in the midst of post-breakup heartache and being manhandled by my supervisor during my lunch break, it all got a bit much, and I did what I—naively—assumed to be the best thing.

I reported him to his supervisor. Others working with me encouraged me to do this, along with one of the other girls who worked there who had actually been having an affair with this guy for a while, and it had just come to an end. At this point, she’d been fired and was reporting him herself. On discovering my situation, we went in together.

I don’t know what I expected to happen. Even at that age, I’d experienced enough of the world to know better than to believe anyone would take me seriously. Yet I was shocked, genuinely, when the guy wasn’t fired. Or even reprimanded. And I was expected to continue working with him. That lasted a while before I grew so uncomfortable and, honestly, ill from the stress that my work performance lapsed, and they fired me. 

That was my first experience having a full-time job. 

You get groped by your supervisor and then fired for complaining about it.

Thankfully, I got another job at a far better archaeology unit, but it was short-lived, thanks to the credit crunch. It wasn’t until several years later, after I’d gone back to university on a PhD scholarship that I was faced with returning to the full-time workforce.

By that point, I’d been diagnosed with bipolar disorder and was undergoing treatment. The meds I took were strong and debilitating. I saw a therapist at least once a week, and I was both physically and mentally in terrible shape.

“Who the fuck would hire me?” 

At length, I concluded that since nobody else was likely to give me a job, I’d have to hire myself. From the box room at my mum’s house, I decided to be my own boss, build my own business, and create success on my own terms in a way that could never be taken away from me.

Fast-forward thirteen years, and I’m writing this from my nice, modern office, from which I run a six-figure copywriting business and a budding digital marketing agency.

Nothing is more liberating than breaking free from the traditional employment structures to be your own boss. Particularly if you’re a woman and those employment structures put you in a subservient position to men, who will take advantage of the power they have over you.

But how, exactly, do you do it?

There are many paths to becoming your own boss. Here are the lessons and methods I learned along my journey to emancipation, financial freedom, and being a lady boss… 

Figure Out Why You’re Doing This

Being your own boss isn’t just about the freedom to work in your pyjamas or set your own hours (though those are definite perks). It’s about reclaiming control over your life and career. It’s about no longer being at the mercy of someone else’s poor decisions or having to put up with toxic work environments. It’s about creating something that’s yours and (in my case at least!) making sure you never have to deal with another handsy supervisor again.

So, why do you want to be your own boss? What’s driving you to break free from the traditional employment chains? 

Freedom And Flexibility

For a lot of people it’s the desire for freedom and flexibility. You want to decide when, where, and how you work. Sick of the 9-to-5 grind? Want to work from a beach in Bali or your cosy home office? Being your own boss lets you set the rules.

Want a four day work week? Nobody can tell you not to. Hell, if you only want to work a few hours a week and spend the rest of it on the beach, you can, as long as/m you’re taking actions in those few hours that earn you the income level you’re aiming for.

For many in positions like I found myself, where mental health had to be my priority for a while and a traditional 9-5 wasn’t really an option, the thought of being able to work on your own terms, in your own hours, is liberating. After the whole getting fired for someone else being an ass incident, I wound up in a very abusive relationship that left me homeless and in a ton of debt. Financial abuse, not to mention regular abuse, often leave women (and sometimes men) in a beholdened position; you’re unable to escape because you do not have the financial means to do so, or doing so would leave you destitute and homeless. 

Financial Independence

The allure of financial independence is also another huge factor for most (if not all) of us. If you’re tired of your salary being dictated by someone else, being your own boss sounds like a dream. When you’re in charge, your income potential is limitless. Sure, it’s risky, but the rewards can be massive. Plus, you won’t have to wait for an annual review to get a raise.

And of course many stay-at-home parents find themselves frustrated by their lack of personal income and the fact they are reliant on their partner, or the government, for money. The need to care for the kids makes full-time and particularly well paid work tough for a lot of people. The thought of making money from home while working around the kids schedules, and only having to put in the hours you want is extremely appealing.

Creative Freedom And The Realisation Of Your Dreams

Remember all those great ideas you had that your boss shot down? When you’re the boss, you get to call the shots. Your vision, your way. No more compromising your creativity or integrity to fit someone else’s agenda.

Likewise it’s an opportunity to finally shut up the friends, family, spouses and significant others who put you down, undermine you, or tell you that hobby of yours is pointless, that dream of yours is never going to happen, that life you’re planning is unrealistic and you just need to knuckle down and get a normal job like the rest of us.

Nothing sticks it to the man quite like living life on your own terms and proving everyone wrong in the process.

Assessing Your Skills and Passion

Alright, now that you’ve got a fire burning in your belly and a solid reason for wanting to be your own boss, it’s time to figure out what exactly you can do. Because let’s face it, a dream without a plan is just a wish. And we’re here to make sure your dream turns into a thriving reality.

First things first, you need to take a good, hard look at yourself. What are you good at? What do you love doing? What are the things that make you lose track of time because you’re so absorbed in them? This isn’t just about identifying skills; it’s about finding where your passion intersects with your abilities. When I initially did this exercise I didn’t quite get it right. I ended up starting a business editing and proofreading other people’s writing, because that seemed like a more ‘work’ thing to be doing than what I actually wanted to do, which was write. And i struggled the first year or two, really struggled, because i wasn’ actually doing what i was passionate about. I was doing what I thought would make a good business. 

When I shifted my focus to what I actually loved, writing, everything clicked and fell into place. So, as you consider these questions, remember the whole point of being your own boss is to build your dream business so it can fund your dream life.

This isn’t about what other people think you should be doing, or what sounds like it’s a real business. This is about your wildest, unfettered imaginings.

Here’s how you start:

List Your Strengths: Write down everything you’re good at. Don’t be modest. This is not the time for humility. Think about your professional skills, your hobbies, and even those quirky talents that your friends always marvel at.

Identify Your Weaknesses: It’s equally important to recognize where you might need help. This is not to discourage you but to give you a realistic picture of where you might need to learn or seek assistance.

Passion Points: What activities or topics light you up? What would you happily do for free because you enjoy it so much? This is crucial because passion fuels perseverance, and you’re going to need a lot of that on this journey.

Finding Your Niche

Once you have a clear understanding of your skills and passions, it’s time to find your niche. This is the sweet spot where what you love, what you’re good at, and what people are willing to pay for intersect. Start by getting a sense of what’s out there. What are people looking for? What problems need solving? Use tools like Google Trends, keyword research, and social media to see what’s trending in your areas of interest.

Look at who’s already doing what you want to do. This isn’t to discourage you but to learn from them. What are they doing well? Where are the gaps in the market that you could fill? What can you do better or differently?

Next, consider what will make you stand out and give you a unique selling proposition (USP). What sets you apart from the rest? Maybe it’s your unique background, a particular skill set, or a fresh perspective. Your USP is what will make you stand out in a crowded market.

Finally, test your idea. Before diving in headfirst, test your business idea on a small scale. This could mean offering a service to a few clients, launching a small batch of products, or even conducting a survey to gauge interest. The feedback you get will be invaluable in refining your business model.

Creating a Business Plan

You might be thinking, “I’m passionate and skilled, what more do I need?” Well, a solid business plan is your roadmap to success. It doesn’t have to be a 100-page document, but it should cover the essentials. Here’s a basic outline to get you started:

Define Your Business Goals: What do you want to achieve with your business? Be specific. Think about your short-term and long-term goals and how you’ll measure success.

Outline Your Target Market: Who are your ideal customers? Create detailed customer personas to understand their needs, behaviours, and how your product or service can solve their problems.

Develop a Marketing and Sales Strategy: How will you attract and retain customers? Think about the marketing channels you’ll use (social media, email marketing, SEO, etc.) and your sales process. Honestly, I found this to be the hardest part when I first started my own business. Back then I knew F all about marketing. I learned the hard way, through trial and error and a hell of a lot of hard work. If you’d like to skip all that, you can just read my book, Divine Blogging, which distils over a decade of learning the hard way and doing it for other people into a single marketing strategy. 

Financial Planning: Start with a budget. How much money do you need to get started, and where will it come from? Consider your pricing strategy and how you’ll manage cash flow.

Sort Out The Money Part

Speaking of financial planning,  this might be the least glamorous part, but it’s absolutely crucial. Your passion will only get you so far without a solid financial foundation. Here are the key components:

Budgeting: Outline all your expected costs – both one-time and ongoing. This includes everything from equipment and supplies to marketing and operational costs.

Funding Your Business: Determine how you’ll finance your startup. Will you bootstrap with your savings, seek out investors, or maybe apply for a small business loan? Each option has its pros and cons.

Pricing Your Products or Services: Set prices that reflect the value you’re offering while remaining competitive. Don’t undersell yourself. Your time and expertise are worth it.

Planning for Taxes and Financial Contingencies: Make sure you’re prepared for taxes and any unexpected expenses. It’s always a good idea to have a financial cushion for those inevitable rainy days.

Remember, you don’t have to actually have any money to start your own business. If you have a skill then you have a marketable service you can offer that doesn’t have to cost an arm and a leg to get off the ground. The power of the digital age is that anyone can be their own boss by simply getting online and offering to do what they do best for others, in return for money. For me, that’s now writing and marketing. When I first started it was anything I could think of – editing, proofreading, formatting, graphic design, illustration, literally anything. And while you need to market yourself in order to earn that money, you don’t need to spend a fortune doing it. You can effectively build a business without spending a penny on advertising, PR, or anything else, simply by creating great content and sharing it.

So, if you don’t have funds to start with, don’t panic. Start with what you do have – you. Leverage yourself and your skills and passions, share those things through content marketing, and once you start to see some money coming in, build on that.

Overcoming Challenges

Building your own business and becoming your own boss is incredibly rewarding, but let’s be real—it’s not all sunshine and rainbows. There are challenges, both internal and external, that you’ll need to navigate. Here’s how to tackle them head-on.

How To Navigate The Challenges Of Being Your Own Boss

While running your own business and being your own boss brings a huge amount of satisfaction and many great perks, it can also be TOUGH. I say this not to discourage you, but to highlight the need to be aware of this before you go in, and also KNOW that it’s tough for everyone. It’s not you. You’re not weak. You’re not struggling. You’re not inept. Anyone starting a business of their own encounters demons along the way. You may have clear sailing for years before you encounter them, but trust me, they’re out there. Self-doubt is the biggest one I’ve had to contend with, coupled (and to be honest massively exacerbated) by caring too much about the opinions and perceptions of others.

Imposter syndrome is an absolute bitch. You’ll likely question if you know what you’re doing, if you have any business being in business, why anyone would hire you (or buy from you, if that’s your business model). You’ll feel like a fraud and wonder how anyone can take you seriously.

And if you have friends and family who don’t work for themselves, who have no idea what you’re doing, how it works, what’s involved, or the potential of your vision and business model, all of that negative self-doubt is very likely to be amplified by their views, opinions, and attitudes. To this day, my mother speaks to me as if I can’t afford basic things, like new clothes, and questions the wisdom of me making purchases of any kind, because she assumes I can’t afford them.

It really can feel like your friends and family are unsupportive and just don’t ‘get’ you. Honestly, I must have had the “Why are you assuming I can’t afford this when you don’t know how much I’m earning?” conversation with her a dozen times. I earn far more than she or my father ever did in their own careers, but because I work for myself she genuinely struggles to understand this.

My grandfather (her father) has an even tougher time because he has a general issue with taking any woman’s job seriously. That’s just his generation and how he was raised. Women didn’t have careers. They had jobs until they married, and if they worked after that, it was a minor source of income and more of a hobby. He’s always struggled to take my mother, myself, and my sister seriously in any conversation concerning work.

Friends are likewise confounded by my work. Most of them work in traditional employee roles and struggle to grasp the potential of working for yourself. They don’t get how I can make money doing what I do. They certainly underestimate the amount of money I can make doing it, and are often shocked when they find out. This can make it really tough to relate to them, and for them to relate to you, on matters concerning work and careers. And that gets SUPER lonely.

The Perceptions Of Other Business Owners

Even other business owners can have odd responses to you as a business owner. My other half runs his own company, just like I do. In fact, we met when I did some work for him and he wound up hiring me for a few years as his head of marketing. When we got together, I went back to working for myself (largely because that had always been the plan, but also I didn’t like the dynamic of being romantically involved with my boss!). He knows how good I am, he knows how working for yourself works, and STILL he often says things that come across as incredibly condescending and undermining. Either because it’s just not how he does things, and he’s concerned, or because we have a very different approach and he (usually) assumes he’s right and I’m wrong.

Men, in particular, struggle when confronted with a woman who works for herself. A woman who has created a business of her own, on her own terms. I by no means mean all men, and for the most part it’s an unconscious bias and not a purposeful form of disrespect. But still, the sexism you encounter as a female business owner is crazy.

When I rented my office—a nice, big, newly built, modern office—I did so entirely on my own. I found the space, spoke to the man in charge of letting it out, negotiated not one but three full months rent-free, visited twice to check out the space, and then returned one final time to sign the contract. That final time I brought Simon (my other half) with me, as he’s in tech and I wanted him to look at all the outlets and setup to check nothing needed adding and see what we’d need to get internet, etc., setup.

From the moment Simon walked in the room, the men involved forgot that this was my office. The guy I’d been dealing with the whole time, as well as his brother (who owns the offices), directed all their questions to him. They asked him enthusiastically about his business. And, despite Simon repeatedly reiterating that this was my office, not his, and my business, not his, and me literally giving them my company details which clearly show it’s in my name and I’m the sole director, they kept talking like my business was really his, and he just let me run it to humour me, or as a hobby, or maybe he just bankrolled it.

It was a surreal experience. They are lovely guys. They’ve never been anything but nice to me. I doubt they realised they were doing it, and if they had, I’m quite sure they’d have been mortified. But this is the shit we have to deal with. A collective social attitude that paints women in business as, in one way or another, lesser than their male counterparts. Dependent upon some man, somewhere, in some way.

Surely behind every successful businesswoman is a man bankrolling her, or advising her, or giving her the ideas, or managing things. The hardest thing to truly embrace as a female entrepreneur is this: 

Behind every successful woman is herself.

Subverting the narratives really is a bitch. To this day the other business owners in my block are a little perplexed by me. Next door I have an office full of women working in a women-owned business, yet they seem to think this is a residential rental and not where I work. Why? I’ve no idea. Yes, I’ve always brought my dogs to the office and have a very informal way of dressing. But I’ve told them what I do. They have my business card.

And still, they think I live here.

On an industrial estate.

In a building that doesn’t actually have a full bathroom, only a toilet, and a miniscule kitchen with no oven.

Like, wtaf?

It’s not just them either, I’ve had multiple conversations with the bloke on the other side of me, and he’s asked me several times what I do, never quite seeming to be able to retain the information. Same with a lady further along the block, who is now (I hope) something of a friend, but still, it took her ages to wrap her head around what I do. 

People will always perceive you through the lens of their own subconscious biases, opinions, and experiences. I am essentially alone in this office, the people who work for me do so remotely and rarely come here in person. I set it up that way intentionally; I enjoy the freedom of working on my own terms, I want them to share that. None of them are full time employees, all of them run their own businesses.

They don’t need to be here.

Yet the concept that a woman alone would have enough funds in her business to spend £1K/m on an office nobody comes to be her, seems to really confound people.

Like, genuinely, they just can’t seem to believe it’s true, and search for other explanations.

Cultivating Your Own Self-Worth

You have to cultivate rock-solid belief in your own abilities and your own legitimacy in order to stand in the face of everything the world throws at you, which tries to undermine and contradict you. Yes, there is also support, and there are also wonderful people and communities who will lift you up, affirm your skills and capabilities and existence. And I strongly encourage you to actively seek out such people and spaces, because you need them and they will help. Aside from anything else, it helps you avoid toxic independence. But even if you have support from like-minded people, you still need to stand in your own power, believe in yourself, and have the capacity to deflect the negatives when they come your way.

Part of the reason I took that job with Simon was the need to beat the imposter syndrome. I was at a point where I wanted to open my own digital marketing agency, and shift from a freelancer with a team I outsourced to into the next stage. But I couldn’t pull the trigger on it. I was so confounded by the fact I was self-taught and worked for myself and really who was I to say I was any good at any of this?

Someone else hiring me to run their agency was validating. And it was a validation I needed in order to get to where I am now. But the fact I needed it is a sad testament to how so many female entrepreneurs (and, I’m quite sure, male ones too!) are made to feel.

Fortunately, I found the thing that convinced me of my own abilities. It required working for someone else for a while, but it worked. I suspect if I’d done a better job of cultivating my own self-worth early on, it wouldn’t have been necessary! Put that work in right from the start.

Trust me, even if you don’t feel you need it right now, it’s better to have a strong foundation of self-belief to fall on if something comes along and knocks you down than it is to get five or six years in and realise even you don’t believe you can do this.

Stick It To The Man; Be Your Own Boss

Starting and running your own business is not just a career choice—it’s a powerful stance against conventional constraints. It’s a journey filled with both immense rewards and significant challenges. From dealing with imposter syndrome to facing the biases and doubts of others, the path to being your own boss requires resilience, determination, and a solid belief in your own abilities. Remember, behind every successful woman is herself. Cultivate your self-worth, stand firm in your decisions, and embrace the freedom and control that come with being your own boss—this is how you truly stick it to the man.

Connecting with other business owners is a huge part of creating your own success and stability. So, feel free to tag me on Instagram, TikTok, or Facebook @RebelWolfMarketing the next time you’re promoting yourself; I’d love to support you and your business. Together, we can redefine what it means to succeed on our own terms.

If you’d like to read more about my journey and learn the content marketing strategy that made my business successful, download the first chapter of my book, Divine Blogging, for free. This isn’t just a guide—it’s a manifesto for anyone ready to defy the odds and carve out their own path in the business world.