An Open Letter to my Past Self


The points made in this list came about because of a recent #ContentClubUK discussion.

For those not in the know, #ContentClubUK is a Twitter-based chat with a bunch of friendly freelancers and content creators.

Each week (Tuesdays at 11AM), a host asks three questions and we all chime in with our advice, horror stories, and general chit-chat. It’s fun and it’s a great opportunity to meet new peers and gain a bit of knowledge (and eat lots of biscuits)

Not too long ago, Indelible Think took over hosting duties and asked some really interesting and valuable questions. One of which was about what advice you’d give your past self.

I’ve decided to expand the answers I gave in my original tweet and, hopefully, explain them a little further. So, if we ever develop time travel, this is getting sent back a decade or two to little Jakey.

1. Get it all in writing 

Honestly, this one is pretty self-explanatory. Even if a project seems like minimal work and it’ll only take you a few hours, get it all in writing.

It’s not just a case of covering your ass if the client decides they don’t feel like paying, it’s about keeping a record for yourself and ensuring your time is properly tracked.

The smallest jobs should still be recorded and contracted.

2. Don’t burn bridges because of misguided pride

I am, by nature, a very impulsive and hot-headed person. I have to take extra steps to watch what I say. It’s a blessing and a curse because some clients absolutely love that I speak freely and honestly.

Others… not so much.

It’s tough to admit it, but in the past, I have lost long-term clients or prospects because of how loose I am with my lips. Especially when I feel I’ve been taken advantage of or treated badly.

I’m learning, however slowly, to deal with things in a forceful way that is still respectful (regardless of if a client deserves that respect).

I’m still me, I won’t be ramming my tongue anywhere to please a client — just biting down on it instead.

3. If you can smell their cologne from a mile away, say no

So, this is — like a lot of things I write — partly a joke and partly the truth. I mean, I have nothing against cologne. I wear it myself.

But let’s just say I’ve never had a good experience working with anyone doused in the stuff. And I’ll leave it at that.

4. Read more books than you think possible and write constantly

You’re a freelancer; unless you’re massively lucky, a decent amount of your time isn’t going to be assigned to doing any one thing in particular.

There will be some days when you wake up and all you’ve got on the to-do list is ‘breathe.’

Use your free time and read, read, read. Then write, write, write. 

Don’t waste the free time you have. Hone your craft.

5. Enjoy the extra free time

Well, this is kind of redundant… [See above]

New freelancers spend so much time worrying about finding work that they seem to forget they have a whole bunch of free time to play with.

Do something fun with it.

6. You’ll get further in your career by being yourself than you ever did from years of ‘acting professional’

I’m very much in the camp of ‘be yourself.’

Constantly, I see tweets and statuses about how no client will ever respect you if you act unprofessional and don’t take yourself seriously.

This might work for some people, and if so, good for them! Keep at it.

Personally, I started making decent money and bagging more clients (who absolutely loved my work) once I started acting more like myself.

Maybe it’s just me?

7. Put aside a decent amount of cash each payday for the slow times

The old adage about freelance life being ‘feast or famine’ is a sad, sad reality that many of us have experienced.

You’re either rolling in clients or scouring job listing boards and crying at 3AM.

It sucks. Big time.

Put aside as much money as you can. You’ll be glad you did next time there’s a famine.

8. Being ‘busy’ isn’t a viable excuse for not exercising more

For way too long, I neglected how important it was to be active and actually get some exercise of a day.

Freelancing can be hectic and there can be days where it feels like you never get a moment to yourself.

You need to make room.

Don’t neglect yourself. Look after your body.

I’ve hosted #ContenClubUK a few times now. If you’re interested in joining in, follow me here and I’ll tell you more about it!

This was originally posted as an article on my LinkedIn page.

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