Could you hack it as your own boss? 21 entrepreneurs tell us how it really is

There’s only one way to find out if the self-employed life would suit you, of course, but it pays to be aware of the challenges you may face.

Let’s hear from a few freelancers and business owners who’ve learnt about those challenges the hard way and reveal what they miss about being an employee…

Amanda Reuben, Bijou Recruitment.
“It’s hard to switch off and to tell clients I’m on holiday. I find it difficult to let people down and am often checking and responding to emails out of hours. There’s always a fear they’ll call someone else if I’m not available. There’s also the struggle to keep a steady pipeline of work coming in, and to be self-motivated. The pressure of knowing only you are putting food on the table creates additional pressure”.

Lynley Oram, journalist and editor
“I never thought I would miss things like appraisals, but the biggest downside of working for yourself is not getting any proper feedback. Also no holiday or sick pay. I guess I never realised I needed validation so much”.

Kathryn Spencer, journalist and editor
“I miss the regular money!”

Nicola Wordsworth, Pup Suds
“I miss paid holidays, someone to cover holidays and sickness, being able to walk away from the job at 5pm…”

Alyson Reay, Sassy Social Marketing
“I have a part-time job as well as working freelance because I needed the balance. Downsides for me included the solitary nature (also I live alone), no sense of team, a feeling of working in an echo chamber – getting good results but no external professional perspective (a client’s perspective is pretty subjective). I also find it difficult to market myself, even though I love marketing clients! So keeping the pipeline filled can be a pressure”.

Lauren Chiren, Women of a Certain Stage
“I really missed having a team around me to brainstorm, challenge and support to doing it all myself until I was able to build up a team again!”

Elena Brennan, Bus Stop Shoe Boutique
“For me it’s really hard to take a day off to recharge my battery. Having a retail boutique and on online store means that it’s constant. It’s hard to stop thinking about your business. Also I pride myself on my customer service, so this in turn means I need to be accessible even if I’m trying to take some time off. I handle all my social media and struggle with whether I should hire someone. I actually enjoy it but there’s only so much we can pile onto our plates!”

Carole Seawert, copywriter
“Well, there are lots of positives, otherwise I wouldn’t still be self-employed after 30 years. But the downsides are: feast and famine syndrome; managing workloads when clients change their schedules; no income when you’re sick; no holiday pay or company pension, company private health insurance; cashflow issues if a client is late in paying. Then there are things you have to pay for yourself like training. I invest a fair bit in training courses each year to keep myself up to speed”.

Debbie Gilbert, Viva Business Support
“My big struggles are lack of security, client boundaries and work life balance. When I broke my leg and needed surgery it hit home that for 3-4 months I still had to work and run a business when if I had been employed I would have had paid sick pay. There is no benefits package – no company car, healthcare, staff party at Christmas – no perks, interaction with colleagues, structure, pension scheme or paid training! I think most people do not research their idea properly or the viability and ask too many friends and family for advice. I was guilty in the early days of not investing in my business which is a massive mistake and one I rectified”.

Diane Watson, financial advisor, She Can Prosper
“Working for yourself means you never switch off”.

Natalie Haverstock, Miss Ballooniverse
“When I’m treating both my clients and my team of freelancers like pure gold to keep them happy, no one’s treating ME like pure gold”

Chrissy Reeves, Back To Life
“I miss colleagues! I do miss people a lot”.

Hannah Hall, Sunflower Events
“Getting the balance right is really hard, as is doing everything yourself vs knowing when and what to outsource. The pressure you put on yourself to perform… Wish I ‘d known more about automation in accounting systems, socials etc at the start – I learnt along the way!

Miranda Levy, author
“I miss gossip in the loos, or by the lifts: where the real intel happens”.

Aarti Parmar-Pandya, brand strategist
You never really get to just deliver your expertise. There’s a whole lot more as a business owner you must be involved in. You end up playing multiple roles until you can outsource. The emotional rollercoaster of running a business from the highs to the lows (sometimes all in one day) can be exhausting. It requires a lot of self motivation, discipline and belief in yourself. You have to be your own cheerleader and see yourself/your business as a brand and not just a business that sells a product & service. That’s been a mindset shift game-changer for me”.

Klementyna De Sternberg Stojalowska, copywriter
“You are the business so even when you are away from it physically, your head is still in it. You need to learn a lot and fast about disciplines that are part of the business machine, but not necessarily your expertise or passion. Even when you outsource, you need working knowledge to be able to have a conversation with that partner/supplier and ask the right questions. This often means spreading yourself thin and doing what you have to, rather what you want to.

Samantha Lawton Skeavington, WIBN business networking
“What do I miss? Paid holiday, being able to switch my phone off, water cooler moments and the Christmas party!”

Jo Tocher, Holistic Therapist
“You have to do most of the work, there’s no one to share the responsibility with! It can be lonely at times”.

Radhika Holmström, writer and editor
“I hate feeling utterly guilty when I do something that isn’t earning money. Other people talk about flexibility: I feel I HAVE to be at my desk and that if I’m not trying to contribute to household expenses I’m a lazy freeloader”.

Caroline Joynson, PR
“I really miss being part of a team and having colleagues. Being part of memberships and groups really helps but it’s not the same as having a cuppa and catch up with colleagues and someone to celebrate with when things go well and to commiserate with when they don’t”.

Julia Sondack, holiday and retreat organiser
“Many of the above but also wish I had set strong foundations and structure with flexibility to grow easily from the start instead of building a business that has needed many changes and adaptations for growth. Without the right foundations it’s been big changes/challenges several times”.

For thoughts from a career coach on the benefits versus the downsides of being self employed read this.

Looking for expert advice? The Audrey Members’ Club is a whole world of support, coaching and expertise for women through self-employment, changing careers, running a business or launching one. Join us to kickstart your future, whatever that may be.