Katie Portman

Journalist. Copywriter. Blogger.

Freelance, Inspiration

Words of encouragement – a letter to my past start-up self

I was on the train travelling to London last week when I suddenly thought how fantastic it would have been, if during my first few weeks or couple of months as a freelancer, I could have seen into the future and realised that my high risk gamble into the world of the self-employed would pay off.

With that in mind, I have drafted a little letter, to my past start-up self. For any wannabe or start-up freelancers / self-employed folk out there, I hope it’ll help spur you on a little, especially if things are proving a bit difficult or tricky currently. For everyone else, remember, that no matter how bad a situation may seem today, tomorrow is a new day.

Here it is. With love, K x

Dear Kate,

Well missus, you’ve only gone and done it! Wooo! Seriously, well done you for taking the leap. You might feel a bit daunted right now, but it’s a very brave thing you’ve just done so give yourself some credit.

In case you’re wondering who I am, I’m your freelance self from the future, about 9 months down the line in fact. I thought hearing from the future you might help you a little, so here I am, to shed some light on what is coming your way!

So come on, own up, how are you feeling about your big move? Scared? Excited? Sick with nerves and worry? Yep, thought so. But you know what, don’t sweat it, these kind of feelings are to be expected. Just accept them for what they are, take a deep breath and battle on. It’s all part of the journey.

Feeling lonely yet? Working on your own is hard, especially because you’ve been used to working with a bunch of people, but you’ll soon get used to it honestly and hey, you can always keep in touch with your ex-colleagues! In a few months, you’ll realise that your productivity has increased and soon you’ll be spending your time with a new group of people – your clients! What’s that amazed face for? Don’t believe me? You might not think it now but trust me, you’re going to be delighted at how busy you will soon become, working for your lovely new clients.

I warn you now though, don’t expect every month to be busy with work, because you’ll soon get a shock. Some months will be VERY quiet (think December) but in the main, before you know it, you’ll have more work than you dared dream of so don’t worry! :-)  You might actually want to make sure that you use the quiet(er) months to ensure that you’ve got everything in order. Now before you start …  I know that you think you’re all sorted, but trust me you’re not. You’ll need insurance, yes insurance, and you really ought to get a decent office chair too, because trust me, sitting on that little stool will do your back NO good at all.

So what else should I tell you about? Well … let’s talk about that the fear and panic you’re beginning to experience. From me to you, don’t expect those feelings to disappear completely anytime soon. In fact, you’ll be much better off if you accept that they’re going to be around for a veeerrryyy long time, popping in and out and causing occasional upset. The good thing though is that soon you’ll actually find that you get used to these feelings ‘being around’ and you’ll get much better at coping with them. However, if at times, everything starts to get on top of you and feels too much, just remember to breathe. Breathe and carry on and remember that everything will be ok. Find that infamous inner fire of yours and tell those niggling doubts to get knotted.

Ok, so what’s left……Well, whether you like it or not, this new career / life choice of yours, is going to create a few ripples. You’re going to face all  kinds of challenges ahead and some of them will be pretty tricky. Expect to lose sleep, because you will. Expect to upset your loved ones, because you will. Expect that you’ll have to chase some clients for your money, because you will. Expect to experience tsunami-size waves of crippling self doubt, because you will. Oh and get ready for a big ol’ dose of negativity and jealousy that’s about to come your way too, because it’s heading in your direction as well. But hey, you know what? All this stuff, these little obstacles, they’re all just part of the experience. Being a freelancer is definitely going to change you as a person, but only for the better, so hold that head up and keep on smiling.

That’s pretty much all I can tell you for now my old friend. The rest, no doubt, you’ll figure out for yourself. Be proud of what you’ve achieved so far, give yourself a good pat on the back and look towards the future with hope and determination.

This is the life you’ve always wanted remember, so go out there and grab it by the you-know-whats! And if you find yourself ever lacking in motivation, just picture in your mind those pairs of ridiculously expensive shoes that you lust after, because from where I’m standing right now, those decadent heels are looking more and more destined to be yours ;-)

Good luck Katie. Be bold, be fearless, be YOU.

Love and hugs,

Your slightly more experienced freelance self (who still has SUCH a lot to learn)



  1. Kate Smith - May 16, 2011 21:41

    What a lovely post – such a fantastic idea! Love reading your work hun, as always xxx

  2. Katie Jackson - May 16, 2011 22:46

    Such a good read, thank you for this from someone contemplating the “jump”! All the best for the future :)

  3. emtwo - May 17, 2011 09:25

    Great post and a novel idea – good read for anyone looking at “making the jump” :0)

  4. Derek Carpenter - May 17, 2011 09:36

    So many people will relate to this. A sense of Humour proves to be a huge support.
    You will continue your journey to great things Kate.
    Every good wish.

  5. Mary Ferguson - May 17, 2011 10:17

    Great blog idea! Reads brilliantly :-) x

  6. Annika - May 17, 2011 11:41

    A fantastic post. I love it! Perhaps you could write a letter to your future self too to open if you ever need a morale boost?

  7. suejeff - May 20, 2011 10:00

    Thanks for this Katie, it’s a really enjoyable post, so nice when someone
    is kind to themselves for a change, which is how it comes across.

  8. Alistair Beech - May 27, 2011 12:23

    A very inspiring read and great to see you’re grabbing freelance life by the scruff of the neck!

    I found this Freelance Manifesto recently – https://www.readability.com/articles/eg1kn9a1 – which gets me going if I’m ever running on empty!

    Keep up the good work

  9. Hayley Toothill - June 20, 2011 00:45

    I took the plunge to become a freelancer this week and ever since I have felt consistently sick with worry and doubt. Everything you have said in this I can totally relate to, however reading how far you have come is incredibly inspiring and reinforces that fact that as scary as this may be, I have made the right decision. Thank you for writing this – I feel a whole lot better xx

  10. Maeve - August 20, 2012 23:14

    I loved reading this. It’s made me want to write a letter to myself in just the same way.. To look back on in years to come. Perhaps I’ll write to myself every year :-) keep it up. I love it!