The Pros And Cons Of Being Your Own Boss

Do you dream big and aspire to do great things in the world? Are you tired of working for someone else? Ever thought to become your own boss one day? Just thinking about the token Girl Boss figure, the glamour of it all is enough to make you shout, ‘sign me up!’ The truth of the matter is being your own boss brings great risk but hopefully with the right execution and mentorship, greater reward too.

It requires substance and grit. Thinking about the Girl Bosses in your life, they probably demonstrate qualities like strength, determination, perseverance, adaptability, commitment, awareness and humility. Among many other things, this is what it takes to learn, grow, make mistakes and learn some more. Being a career girl yourself means great things as you’ll have skills to bring into starting your own business – what a way to start!

Being an ex-personal assistant myself and now my own boss (thank goodness!), I dream of a day where more Personal Assistants, Administrators & Office Women struggling with the  9-5 grind can start their own businesses and become their own Girl Bosses… And can I just say the pros by far weigh out the cons. Which is why I started my business! If you want to become your own boss, consider just a few of these pros and cons.


1. You have complete control

Forget having to ask for permission, creativity will be the star ingredient for your success and if you play your cards right, you can work anywhere in the world, on the hours you set for yourself. Cocktails, poolside, laptop = paradise & is totally possible. Up to you.

2. All credit goes to you

Quite often the recognition gets lost working for other companies/businesses. Instead, building a successful business on the merits of your hard work speaks volumes and before you know it, you’ll have something you can be very proud of.

3. You’ll learn and grow in ways you never thought you could

As goes the token interview question, ‘why do you want this job?’ most will probably say, ‘to learn and develop new skills.’ In other words, you’re bored and you need more. Instead of a steady drip of the tap, being your own boss will be more like a tidal wave of new information and sometimes you will feel like you’re drowning. Enjoy the learning experience and swim, swim, swim.


1. Your clients become your boss

These people are your number one. The feeling can be a lot like running on a treadmill with a stitch but instead of being able to stop, you will have to run harder. Don’t worry, it can be such a meaningful position to be in but a heads up – the notion of becoming your own boss isn’t necessarily that you get to work less. With your name on the line, you will want to work harder.

2. Starting a business can be hard

Like looking after a newborn baby, you will be sleep-deprived, lacking energy and most likely out of pocket before you start making some real money and if you feel low on motivation, there’ll be you and only you to pick yourself up and battle on somehow.

3. No more security with a steady paycheck

It’s a safe feeling knowing that you have money coming in at a certain time of the month; enough to pay the bills and that’s it. Becoming your own boss means you will have to paddle your little heart out to replace the income.

While being your own boss can be stressful in the beginning, the possibilities are incredibly endless as to what you can achieve. Truly helping people, leaving your mark on the world in some way and becoming abundant in every way makes it all so worth it in the end. So what would you rather do? Become your own boss or be the busy bee and leave the business decisions up to someone else?

By Georgia Kershaw

Featured Photo Courtesy Of: Nordstrom

  • Heather

    What a great post about what it entails to be your own boss!


  • Gala

    Thank you Georgia for this inspiring post! I just quit my job and started my own business. Scary, but so motivating at the same time! I get so much satisfaction from it and I didn’t regret my decision for one second.

    Good luck with everything!

    Love Gala

  • Posh, Broke, & Bored

    All this, and then some! This summer my boyfriend and I opened a vintage boutique in trendy Shoreditch, London and ever since then my life oscillates between YAAAS I GOT THE POWER (SLAAAAY) to OH GOD SO MUCH RESPONSIBILITY FORGET THIS I JUST WANT TO BE A SIMPLE PEON. Being your own boss is part-terrifying, part-elating, but there’s no denying its a learning curve like no other! x

    Jasiminne | Posh, Broke, & Bored

  • Dani Watson

    Great post Georgia!! I think that so many people want to be their own bosses yet are petrified of giving up a stable job for something that’s a bit of risk but we don’t necessarily have to be quitting our jobs straight away! I’ve seen so many successful women build businesses as a side hustle before they become their full time job and if you do want to quit your job, it’s sensible to create a financial buffer before taking the leap. That business isn’t going to be surviving for very long if you can’t feed yourself! My advice for anyone who wants their own business but doesn’t know where to start is to think about the small steps they could do today – it could be as simple as registering a domain name. Loving reading your posts Georgia. Keep them coming! xxxxxxx

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