262: To Step Out The Boat or Stay Put

I’ve been thinking about jobs, careers and things like that a lot recently. I’ve been in my current job for about four years and although it’s okay, it’s not what I want to be doing forever and eternity. I’ve polished up my CV and sent it out for a few jobs but nothing’s really happened.

I got thinking about self-employment and whether I had what it takes to be self-employed. It kind of runs in my veins with both of my Grandfathers being self-employed and my Mum and Uncle are both self-employed but at the same time do I have the motivation, direction and determination to be my own boss.

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While I work in an office I have a level of accountability to get on with my work and not get distracted by other things. If I worked at home would I get distracted by the cleaning and things like that? Then again by being at home to work would I get more stuff done because the house would need to be tidy for me to work. Then we have the whole thing about space – do I work in the shed? It’s got electric so it would just need tidying up and during the winter I could have a fan heater on and thermal pants if required.

Then there’s things like what do I need to do to get started, do I take a week off on holiday from my day job to see if I can behave myself and do the self-employed thing, do I work and save up money to create an emergency fund of sorts to top up my earnings to cover bills if I don’t have enough (then again as sensible from an economic/business mind, does this mean I’m not trusting that God would provide for me – then that’s a whole other theological conversation to be having for another day I think!)

Then I think about technology – will my MacBook cope with being used 20+ hours a week and if I need to replace it do I go for a MacBook (with Office for Mac as that seems to be a bit of a need) or do I replace it with a Windows based laptop with Office (guess which is the preference!)

This evening after work I went to chat to my Mum and she gave me a list of things to do and ideas to come up with. Some including getting extra IT qualifications under my belt so I can show what level of skill I have when it comes to things like Excel and Word rather than just saying I’m an Advanced User. I’ve done two free courses online this evening (two x 40 minute assessments that I did in about 20 minutes total) I could apply for the certificates but it was like £15 for two hard copies – can’t they just send a PDF so I could print it myself? Oh well.

If you’re self-employed how did you end up doing that rather than working for “the man”? Would you go back to working for “the man” or would you do your best to stay self-employed?


  1. ianbraisby says:

    Could never go back to working for someone else after 12 years freelance. I even find it hard working with a business partner on our tours and ghost walks. I was very lucky in that I was considering making the break, did it for a while in my spare time to be sure I was capable of doing the job (translation) to a high standard and then, while I was dithering, I was made redundant. So I no longer had anything to lose and said I would give it a couple of months to see if it took off and if not start doing agency work and looking for another job. And here I am! My main advice: (1) Identify what work you would do and that there is a genuine market you can tap into as an independent; (2) Decide whether self employment is the best route, as there might be other jobs in the same field that are more appropriate, equally fulfilling and lower risk; (3) Don’t ignore the negative aspects – instability, no company pension, no paid holidays or sick pay, isolation of working on your own – as it’s all too easy to focus solely on the positive things and this brings unrealistic expectations; (4) Make sure you have the discipline and commitment – it is a great lifestyle choice for many people but be prepared to put in lots of hours, often at times not of your choosing in the early days when you’re getting established, and to often blur the boundaries of work and private time.
    In terms of preparation, IT courses would be a secondary thing in my opinion. Experience in an office environment using packages is rarely accompanied by formal certification, but is generally considered perfectly adequate in demonstrating ability. The key thing you need to be up on is marketing and business development – loads of online or night school courses available on this. Also loads of things you can get online to do with using blogs and social media to help promote your business – ask SJB about this, she has used quite a few of them.
    Any other help you need, just ask! Good luck.

    • Hannah says:

      Hey Ian!

      Thank you for the essay! I love long comments (and short ones, and middle sized ones as long as they are encouraging and positive rather than mean and negative lol.)

      I think the idea of being my own boss scares me, who’s going to beat me back into line when I’ve got sidetracked. Who’s going to tell me whether I’d doing a good job and doing the right stuff rather than focusing on the wrong stuff.

      I think I’ve got an idea what I want to do and I am pretty sure there is a market for it, it’s just a case of getting into it and being able to earn money from it lol.

      I know that my Mum works funny times to make sure she gets everything done. I go round some evenings and she’s been going since 8am and is still going and it’s nearly 6pm, whereas if she was in a normal office job she could start at 9am and finish at 5 and be home in front of the TV by 6pm. But actually I don’t thinks she’d change it, given all the extra bits and pieces she’s managed to achieve.

      I get so many responses saying that I don’t have enough experience if I can gain a few more qualifications while working the FT job then hopefully they will benefit me in the end even if to show what I can do.

      I think I’ll be taking a lot of advice as I can get it lol.

  2. Rickie J says:

    I would encourage anyone who wants to go freelance/be a business owner. However, the first important bit of advice is to build your business up first rather than quitting the day job.
    When you have built it up to a sure level, go part time – or find a part time job that you love doing rather than FT that you don’t. This way, you have steady income from part time job, plus some income from the business, whilst you still build it up. And on that note, a whole heap of advise when you need it!
    Hope that helps for now.

    • Hannah says:

      Hi Rickie,

      No I’m not at the point of quitting the day job – I think when that stage comes I’m going to be petrified and might also have to make sure that my Manager doesn’t have a heart attack or something! Before that happens I need to make sure I can raise an “emergency pot” and cover the bills, and also find something to focus on with regards to the business idea. I think I need to work out what’s the minimum I need to earn in a month (whether it’s from the business or a part time job) and then go from there. I know how much I get paid at the moment but that has spare in it for treats etc.

      Between you, Ian, Clare, My Mum and My Uncle, I’ve got a whole bunch of advice coming out my ears and a whole bunch of guidance which will be good.

  3. Claire 'Elle' Field (@ellefie) says:

    My biggest advice is that I would say make sure you have a reserve pot of money to pay the bills, purely because getting paid on time is a nightmare. I’ve only ever been paid once on time so you can be waiting for a long time to get your money. Sucks, but it’s very common.

    The plus points for being self-employed is the flexibility and freedom it affords but you can start to feel a bit isolated if you’re working from home all the time. It’s swings and roundabouts, as with anything!

    • Hannah says:

      Covering the bills is the biggest thing that stops me taking the jump I think. With regards to the accounts and things like that my Mum can help me and she has other contacts for bits that have to be officially done like tax returns and other bits.

      I like the ability to be a bit more flexible – especially with all the extra meetings we have to attend with Our Sidekick living with us. My Manager is pretty flexible when I can give him enough notice and as a father he understand that’s it’s not always straight forward and life doesn’t always come with advance warning systems lol.

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