Considering Leaving Management to be Your Own Boss? Do You Take the Leap or Dip Your Toe?

The world of work is changing rapidly. As life expectancy increases, millennials are now predicted to be working much later in life – some of us well into our seventies! 

Multi-stage career paths have replaced the ladder climbing approach of previous decades and this is resulting in thirty-something professionals reaching management positions and questioning their situations.

This makes sense as most jobs lose a certain amount of allure a few years down the line. Further to this, concerns about stagnating career progression, coupled with gradual disillusion in regards to perceived politics and pettiness in the boardroom can become very draining. Moreover, being good at a job does not naturally mean that you will suddenly love managing a team of others. As a result, many professionals are asking themselves; “Is this what I really want? Do I want to work my way up through to senior management? Or would I be happier being my own boss?”

For many, it’s all about finding the freedom and the flexibility to work how we want, according to a recent article by Forbes. Over 62% of millennials have considered starting their own business, with 72% feeling that start-ups and entrepreneurs are a necessary economic force for creating jobs and driving innovation.

The media is inundated with inspirational, start-up success stories from Sir Richard Branson to Sir James Dyson, selling us the dream that creative flair, an astute business mind and hard work are all that is required to fuel the next entrepreneur to turn rags into riches. The potential rewards on offer can be enticing and that’s why career choices can seem more empowered with every reported start-up success. So should you take the plunge, leave your job and focus solely on your new venture? Or go for a ‘halfway house’ approach?

Today there is a wealth of additional income opportunities for side businesses such as renting a property on Airbnb, opening an eBay store, teaching, freelancing or even starting your own online business, to name just a few! However, for some, the need to free themselves completely from the monotony of a nine to five cannot be compromised. While there are of course clear risks associated with starting your own business, from abandoning a steady pay check to investing a huge amount of your own time and money, the key for those leaving the security of a full-time role, either partly or fully, is to recognise the changes that the new workplace will bring.


It can be quite a culture leap, going from a busy office to working alone. This will be the case for most new ventures whether you’re starting a dog walking or online retail business. Co-working spaces like We Work and freelancer coffee shops such as Ziferblat provide company and a professional yet friendly working environment. Additionally, local meet-ups are organised all over the UK to cater for the growing community of lone workers.


Admin still has to be done! And as many have discovered, it can take up a lot of time. It’s worth considering a support service such as The remote PA to help with some of the more time consuming tasks.


Are you going to be a limited company, or a sole trader? How you operate will impact on your tax liabilities and the advice from most self-employed people is to get a good accountant straight away. They will steer you through the joys of HMRC and could be worth every penny in the long run.


Don’t assume you can just start working without a back-up plan. If you’re ill, or your work dries up, or your home office gets damaged, you will need good cover. There are several very easy-to-understand policies on the market which can be tailored to the industry you choose, so it’s wise to speak to a broker who can advise on start-up and small business insurance to find the right product and protect your interests from the outset.

Work-life blend

A work-life blend, not balance means taking your laptop on holiday, working in the evenings, never leaving your phone behind; however, it can also mean morning coffees with friends, a run at lunchtime and more time with the family! There are pros and cons and only some feel the benefits more than the burns ‒ remember the saying “more than half of new businesses fail during the first year”? Well according to the Small Business Association (SBA), this isn’t necessarily true as it states that in the US, more than half of small businesses survive for five or more years, and about a third of them survive for more than ten years; although, remember that for all those that succeed, many others fail.

Taking the plunge involves risk, but it allows you to focus entirely on your new endeavour. The ‘halfway house’ approach will involve a lot of juggling and could have quite an impact on your free time, but it removes some of the risk.

The key is to do proper research into whether your new business is viable, and know how long you can focus on starting and building it. With support from third parties, a good business plan and a passion for your project, it could be the best move you ever made!

Charlotte Giver

Charlotte is the founder and editor-in-chief at Your Coffee Break magazine. She studied English Literature at Fairfield University in Connecticut whilst taking evening classes in journalism at MediaBistro in NYC. She then pursued a BA degree in Public Relations at Bournemouth University in the UK. With a background working in the PR industry in Los Angeles, Barcelona and London, Charlotte then moved on to launching Your Coffee Break from the YCB HQ in London’s Covent Garden and has been running the online magazine for the past 10 years. She is a mother, an avid reader, runner and puts a bit too much effort into her morning brew.