01 December 2022

What's the plan? A DIY career development workshop for freelancers


Most companies have career development paths and dedicated times for reflection and planning. As a freelancer, you need to create this time for yourself. And there's no time like the present...

The Choix team have put together a set of kickstarter exercises to help you build a development plan for the next 12 months. They’re designed to be completed over the course of a week - 20 - 40 minutes a day.

So go on, make a cup of something, and let's get cracking! 

Exercise 1: where you were

It’s good to start with a recap of the journey thus far - what were the highlights, what challenges have you’ve faced?  Grab your paper, and make a timeline - with the date you started freelancing at one end, and today’s date at the other. 

1. (5 mins) make a project list on your timeline

There’s no need to be forensic re order / exact number - just get them down with rough details as best you remember - i.e. “brand strategy review, BRH, 6 months, team lead - reporting to CMO, via agency, £800 / day". If you've been freelancing for many years, focus on the last 3.

2. (5 mins) score each project out of 5 for:
a) success b) enjoyment c) development opportunities 

i.e. each project will end up with 3 numbers next to it - i.e. “brand strategy review, BRH, 6 months, team lead - reporting to CMO, via agency: success - 1; enjoyment - 5; development - 5. 

3. (5 mins) now rank your projects, best to worst, in terms of success, enjoyability and development 


4. (10 mins) cast your mind back and answer the following questions. 

  • Why did you start freelancing initially?
  • What did you think the benefits would be - back at the beginning? 
  • What did you see as the potential downsides? 
  • List 3 highlights / successful moments - the first ones that occur to you, from all the projects you’ve listed: be specific about the particular moment. I.e. BRH board presentation - finally everyone on the same page, listening, great questions - consensus achieved! 
  • List 3 lowlights - again be specific.

5. (5 mins): make a list of the main skills / areas you’ve developed in while freelancing

Headlines are sufficient i.e. detailed knowledge of crypto industry (from nothing), pitching for business, board presentations

Now, read over your answers, and put them away - don’t add anything, just let what you’ve written sink in - and you’re done for the day! (N.B. If you’re doing the exercises in one go, get up and have a short break - walk into another room / round the block, before moving on.) 

Exercise 2: where you are

Sit somewhere else in the room - e.g. the other side of your desk: change the space a little from the last time you were in it.

Please note: there’s some freewriting in this section. If you’ve never done freewriting before, the idea is to use the starting text to get going and then to continue with whatever enters your head. Don't edit yourself - just keep writing for the full time - if you get stuck, write any words at all until a new thought arrives!

1. (5 mins) answer the following questions:

  • Why are you freelancing now?
  • What are the key benefits? 
  • What are the challenges? 

2. (5 mins) freewrite, starting with I add the most value when… 


3. (5 mins) make a list of your strengths

What are you particularly good at - what do clients call on you for? What would you be super happy to teach / give pointers on to other consultants?  

4. (5 mins) make a list of your weaknesses 

What are you not comfortable doing? Where has feedback not been so good? 

5. (5 mins) review your lists. Underline the strengths that you want to continue to develop; and the weaknesses which are actively getting in your way, and really need attention

I.e. if there’s something you’re great / less good at, but it's not important to develop in this area, don’t underline it. 

Read over what you’ve written. You’re done!

Exercise 3: where you’re going

Change the space again for Exercise 3: go into another room, sit somewhere you don’t normally work. Pop some good, relaxing music on your headphones - whatever makes you feel focused and free (Spotify's Ambient Dreamscapes playlist is a good go-to for the Choix team...!) 

1. (10 mins) you’ve just retired! Your glittering career has been profiled in a magazine. Oh yes it has... Imagine you’re the journalist - you’re writing the last section of the profile for a deadline in 10 mins. Freewrite, starting with the following: “2022 was a turning point. What came next was incredible. [He/She/They] went on to …

This is about the Disney version of your future, so be wild, bold, let your imagination go - there are no limits, no rules, just keep writing!

2. (5 mins) outline the project of your dreams: the project you’d most like to do next.

  • Who will you be working with? (industry / people)
  • What’s the initial problem / scope? 
  • How long is it? 
  • What do you want to achieve? 
  • How do you want to feel at the end of it? 

3. (2 mins)  make a list of 3 career-related things you definitely want to achieve in the next 12 months. 


All done! You know the drill - read it through, then step back. If you’re doing the exercises in one go, make sure you have a decent break here. Eat, have a walk - take some proper time out, let the exercises sink in a little.

Exercise 4: Goal setting

1. (2 mins) complete either one of the following

I have a clear sense of my career direction and in 5 years I am aiming to be…
I am currently unsure of my long-term career direction, but I know that in the next year I am keen to…

2. (5 mins) answer the questions in terms of the next 12 months: 

  • How do you want to work?
  • Who do you want to work with?
  • What do you want to do?

3. (10 mins) make a list of development goals - large and small. 

Write down everything that comes into your head: what do you want to improve / develop / learn in terms of your skillset? Are there particular clients you want to approach? Industries you want to work in?

4. (15 mins) read back over what you wrote for Exercises 1-3. 

  • Do you want to add anything to your list?
  • Categorise your list into short, medium and longer-term goals
  • Categorise your list - either: need external training / support OR can achieve in-project

Exercise 5: Make a plan 

(This one’s probably most useful done on a laptop). 

1. (20 mins) take your goal list and flesh out the detail for each development goal

Are there multiple steps involved in getting to a certain goal? List them out. How are you going to achieve each one - i.e. do you need to research training courses / get a coach to help / book a chat with someone in your network who’s an expert? If you need ideas, there are more tips at the end of this article. 

2. (10 mins) choose 3 key goals for the next 12 months and schedule your plan of ACTION!

Make sure you identify how you’re going to measure progress and how you’re going to be accountable 

3. (10 mins) go back to your goal list - are there any additional ones you are desperate to add that you can fit into the schedule? Put them in! 

Congratulations, you’re done!

Next steps: get together with a peer / your mentor / your coach and talking through your plan, getting them to challenge / add to it. Maybe you can meet them again in 6 months for a check in? 


A few extra tips...


Do a mini review after every project: what worked, what didn’t, what did you learn, what are the key take-aways? Score yourself - overall and for different elements. Drill down from there. An hour spent doing this at the end of a project is well worth it, however senior you are. 

Always ask for feedback if you can: maybe it’s over a coffee / maybe it’s an email - so long as it's appropriate, always try and do this. 

Keep training / knowledge-building: are there areas of knowledge that you keep meaning to polish? Do you need a course, or is there someone in your network who you can book in for a brain download? (podcasts and audio books can be brilliant here - and you can listen at double speed (!!) if you're after a quick fix). \

Think laterally about training too. For example, even if you're not a coach, a coaching / facilitation course can be a great investment - in reality, most consultants spend a lot of their time coaching and facilitating, so learning the basics can give you a real edge.

Keep your profiles updated: communicate your career as it changes - make sure the kinds of projects you're looking for are reflected in what you're saying on LinkedIn / talent platforms. 
Consider getting yourself a mentor / engaging a coach: it can be extremely helpful to have someone external, who can act as a sound-board / challenge re your development plans. 

Pro-bono work: maybe there’s something you want to get into but you’re unlikely to get there by being paid - is there anything you can do for free that might give you a toe in? 

Volunteering join a board / get going with a passion projects: a huge bonus of freelancing is that it can give you scope to do other projects that light you up - writing a book, making a movie, selling your jewelry on Etsy... These projects will definitely give you energy and a different angle on the world - which is always a good thing - and most of the time you'll learn transferrable skills too!

Keep networking: the more connected and in touch you are, the more you will passively as well as actively learn, the more likely it is that opportunities will to come your way, the better you can service your clients / build teams...the benefits of a great network are endless. 


And finally, look after yourself . Loneliness is one of the biggest issues for freelancers. Burnout is another. If you’re feeling isolated / don’t have enough time to go for a run / see your kids, your career will suffer too. So take stock, and reach out for support if you need to.  

At Choix we help freelance consultants to connect with great opportunities. If you have questions, please email us at hello@mychoix.com, and click here to apply to join our outstanding network. 


Additional articles that may be of interest include our Tips for Freelancers, collated from conversations with Choix Network members and Who Am I - a guide to positioning yourself as a freelance consultant. 




What are you particularly good at? What do clients call on you for? What would you be super happy to teach / give pointers on to other consultants?