Why Being “Bossy” is Actually a Good Thing in Business

“Elise, stop being so bossy.”

That’s a sentence someonein fact, a few peopletold me early in my life. I was always the kid who wanted to be in charge. Sometimes in a pushy way.

One of my favorite games as a kid was being a teacher. I’d rope my brother into doing science lessons, where I’d direct him to drop things in a bathtub of water. I’d make him predict whether it’d sink or float, then drop the object in. I’d mark his work based on whether his prediction was truepretending I was a science teacher.

(Looking back, I’m sure my 8-year-old brother had much better things to do than drop things in the bathtub.)

That all stopped when I reached high school. Pre-teen self-doubt and anxiety crept in. I wasn’t comfortable being “bossy” anymore because people around me were already doing it. And they were doing it better than me. I wasn’t a cool kidfar from it. What right had I to boss them around?

As you can imagine, I fell into a shell of my “bossy” self. I became the sheep of the group, following what my friends did. (Essentially, being the total opposite of bossy.)

That continued with me when I got my first job at a marketing agency. Years of putting myself down and comparing myself to my friends meant I’d developed social anxiety that I’d just finished therapy for. I was petrified to be anywhere near “bossy”, thinking it was a bad thing. So, I:

  • Never put forward my ideas
  • Never pushed ideas I really believed in
  • Never took control over what type of work I wanted to do

I also saw that men were praised for being bossy; women weren’t. A female co-worker of mine, who ended up being a great friend, was bossy and she was slated for it. But her male counterpart was praised.

My approach to bossiness changed when I quit my job to start freelance writing.

It taught me how to be bossy again—and why that’s actually a fucking awesome thing.

(Disclaimer: By “bossy”, I mean not being afraid to stand up for what you believe in, and making recommendations based on that–but also being open to feedback from others. I don’t mean shouting “DO THIS” to everyone you’re working with. More on this later.)

I learned the hard way that bossy = good

That’s a lesson I learnt fast.

I’d quit my job a nervous wreck. I’d never put forward my ideas because of what people thought, nor answered the phone to one of our agency clients.

My freelance business needed both to do that.

I had to pitch ideas to clients and direct them on their content strategy. After all, they were hiring me to be the expert. I couldn’t deliver that if I was too afraid to send them my ideas.

Second, client calls are inevitable as a freelancer. Your client wants to know there’s a real human on the other end, and a face-to-face call gives you chance to run through a brief before sending projects your way. There’s no working around them.

Guess what? You need to be bossy to succeed at both of those things. And business, in general.

I’m not just talking about how being bossy is essential if you’re to thrive in a huge, white male-dominated businesses. (Whilst that is true.) I’m also talking about 1-person businesses; the freelance jobs you’re doing on the side of your full-time job, no matter how small they are.

Let me explain with an example. One of my first clients was a solicitors firm. They were hiring me to write 500-word articles, that were basically keyword-stuffed shit, for them to put on their landing pages.

By month 4, I was getting frustrated. My client wasn’t seeing any results because the structure was so bad, but it was based on the brief they’d sent me. I was working to the brief to a T, taking my client’s word as gospel. I didn’t have any imput; I was just there to put their thoughts into readable sentences.

I knew it wasn’t good content. But I still did it for 4 months.

Why? Because of my irrational fear of being “bossy”. I didn’t want them to think I was undermining them by changing the process, and telling them that keyword-stuffing won’t get them anywhere.

That changed when my confidence started to grow. I started small, testing the waters on how my client would take my “bossy” side. That looked like a steady stream of suggestions, such as:

  1. Including more than one keyword to avoid stuffing
  2. Combining a few pages together that have the same concept
  3. Changing the entire outline to be more SEO-friendly

Guess what? They accepted every. single. change—no questions asked.

Here’s why being “bossy” makes you great entrepreneur

These days, I don’t think being labelled “bossy” is a bad thing. Far from it. In fact, I think it’s a skill every entrepreneur needs if you’re to have a thriving business. That’s because:

1. You don’t get sucked into shitty work

This one is simple: If I’d have been bossier from the start of my first client partnership, I’d have 4 months of work I could add to my portfolio. But because I didn’t have the confidence to be bossy and tell them that the work I was doing was shit, I couldn’t add it.

That was a huge sucker for me. A good portfolio is any freelancer’s bread and butter.

Without one, you can’t convince anyone that you’re a good writer. You also can’t convince anyone to pay you for said writing. A bad portfolio is almost as shit as not having one at all.

2. You build your reputation as an expert

Speaking of portfolios, a good portfolio shows you’re an expert. Clients want to hire experts.

Let’s flip the switch and say you’re the one hiring someone. You’re a freelance writer looking to hire a virtual assistant because you need help creating a client onboarding sequence. You interview two people:

  • Person A: Works exclusively with freelance writers, and only offers email onboarding services
  • Person B: Works with everyone, offering any service

You’re more likely to hire person A, right? They offer a service that’s specific to you. They’re the expert in exactly what you’re looking for, rather than a jack of all traders (and sometimes, master of none.)

(If you’re interested in niching down, I was lucky enough to watch Val Geisler’s talk on specialisation as a business tactic at Learn Inbound last year. I highly recommend watching if you’re running a niche-less business.)

So, how does that tie-in with the “bossy” mentality we’re talking about?

You can’t position yourself as an expert if you’re not putting forward your ideas. You need to rely on those bossy tendencies to make recommendations to clients, explain why what they’re doing is wrong, and give them a solution. That’s what experts do.

Otherwise, you’ll get stuck in this vicious cycle of doom:

freelance cycle of doom - being bossy in business

3. You build a business you actually enjoy running

If I could sum-up what I learnt in childhood in a single sentence, it’d be this sentence my dad said on-repeat: “Love your job and you’ll never work a day in your life.”

I don’t totally agree. I love what I do, but it’s still work. I’m happy to sign-off on a Friday night, enjoy my weekend, and start work again on Monday. I have a work/life balance, and treat each as a separate life.

But the concept is true–and being bossy helps you enjoy your job. A lot.

You don’t want to build a business you hate. You don’t want to sit at your desk clock-watching, looking for ways to make your work more fun. That’s probably what happened at your 9-to-5, and a reason why you left to go it alone.

If you’re not being bossy and demanding what you want from your business, you’ll grow to hate it.

For me, fulfilness and happiness comes when I’m feeling challenged.

But I didn’t I feel that way with my 500-word, shitty keyword-stuff articles for my solicitor client. I didn’t enjoy the work; it wasn’t challenging for me. It was simply taking notes and turning them into readable text. Not exactly rocket science.

I grew to hate my business because of it. Yet when I started pushing back on my client’s orders and suggesting ways to improve it, I was being challenged in many ways:

  • I had to communicate my ideas well (and be convincing enough for the client to agree)
  • I had to do extra, in-depth research to make sure my suggestions would actually work
  • I was writing in a new style that I needed to practice

Think about the opportunities you’re missing out on because of your fear of being bossy.

Are you stuck in the cycle of low-paying work because your client doesn’t see you as an expert? Is your client missing out on $10k more revenue because you’re not bringing your SEO expertise to a project? Are you missing out on referrals because your client isn’t confident to recommend you to someone looking for services you offer?

The bottom line: Everyone is missing out if you’re not being bossy. Especially you.

Being called “bossy” can be a good thing

My fear of being “bossy” is long gone. I know that sticking up for myself and my ideas is something I need to do–and you probably should, too.

But before we part, I want to leave you with one thing: Don’t let bossiness turn into stubbornness.

Part of why I’ve managed to grow my business so well is because I’m open to other people’s feedback. I share my opinion, hear others, and try to find some middle ground if we’re on opposite ends of the spectrum.

The bottom line? Share your thoughts and be passionate about them. But accept that sometimes, you’ll be wrong. Don’t be too stubborn to accept it. It won’t do you any favors.

Enjoyed this? Don’t miss my next ramble 💌

Hey! I'm Elise, the founder of My9to5Sucks.com. I started making money online back when I was 12 years old. Since then, I've started multiple online ventures to grow, save, and invest the money I make—including a 6-figure freelance writing business by the age of 21. This blog documents the no-BS ways I make/save/invest money and build a career.

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