How to improve your business with a freelance retreat

Freelance retreat

Being a freelancer or small business owner has many benefits. You can choose your hours, choose your clients, choose your service offerings…but one of the downsides is that it’s easy to fall into a rut. If you don’t take the time to reflect and plan, you may end up finding yourself working reactively instead of proactively, with your business headed in a direction that’s less than ideal. It’s hard to find the time to work on your own business when you’re in the trenches: phone constantly ringing, emails arriving 24/7, and home life possibly providing even more distractions.

May I suggest – the Freelance Retreat.

For most of my working life I was employed by a variety of organisations in a range of sectors: education, government, non-profit, corporate. The one thing all of them shared was the tendency to force its staff into periodic David Brent style corporate workshops, sometimes complete with PlayDoh and Lego (I wish I were joking). At the time I usually found them pretty tedious navel gazing exercises, but now I have my own business I’ve come to appreciate the value in having intentional strategies and goals. Without them, it’s possible to just tread water, having no idea if you are truly fulfilled, if your clients are happy, or where you will be (or want to be) this time next year.

Every year (or thereabouts) I now take myself on a one person Corporate Retreat. I take it seriously, with sessions from each of my “departments” – HR, Finance, Sales & Marketing, and IT. Lest things get too dull and grim, I make sure to include some self-care and fun activities as well. For me this is somewhere pleasant to go for a run or walk, somewhere with a nice day spa and decent places to eat at the end of a gruelling day.

Where to hold your solopreneur retreat

I generally work from home, and so I like to hold a retreat a 1-2 hour drive away. Not so far that it’s impossible to come back in a family emergency, but far enough to provide a clear mental and physical break. I’m based in Melbourne, and I like places such as the Yarra Valley, Daylesford, the Mornington Peninsula etc. just because it gives me a mini-holiday. I think you could equally successfully go to the city or even just somewhere out of your house like a local library. As long as you can leave behind your normal life with all its distractions.

Preparing for your freelancer retreat

A few weeks before I go away, I send a survey to my past and current clients, as well as my subcontractors. For my clients, I ask a range of questions about quality of work, cost and communication, and what they would like additional help with. My colleagues receive just a few quick questions about speed of payment and quality of brief. I make the survey optionally anonymous. 

If you have the time, it’s a great idea to get some of your data ready to go, so you don’t spend your valuable retreat time bogged down generating reports. I’d suggest preparing:

  • Survey results
  • Financial reports such as your Profit and Loss statement, outgoings etc.
  • List of current clients

What to do in your retreat

Of course, what you work on is entirely up to you, and depends on how much time you have available. As my retreats are 2-3 days, I try to make them as comprehensive as possible.

Overview and Self Analysis

Survey results

Analyse the results of your customer/colleague client survey in Google sheets or Excel. Charts are good if you can generate them quickly – the idea is to get an overview of what’s been working well for you and what needs improvement. Don’t get caught up in making a beautiful presentation – nobody is going to look at it except you! If this is not your first survey, take some time to see how you are tracking over time, and what’s changed.

If you have previously set yourself goals, now’s a great time to revisit them. Did you meet them? Why, or why not? 

SWOT analysis

  • What are your strengths and weaknesses? 
  • Where are your growth opportunities? 
  • Where are your threats? 

Keep in mind that as a one-person show, you need to look at this from both a personal and a “company” perspective. For example: a personal weakness of mine may be a particular lack of knowledge. But a strength is knowing a colleague who has this exact skill. A threat would be losing that colleague. So what to do? Either skill up, or expand the network.


If you have never done this before, I’d recommend it to give you more of an insight into how you can best align your values with your career. If you value family more than anything, working 20 hour days is not going to make you happy. If you value altruism, perhaps you can consider skilled volunteering. You get the idea.

Once you have got a good feel for your own values, strengths and weaknesses, you’re in a great position to evaluate your clients. One exercise you might find helpful is to rank your clients on a range of qualities, such as how pleasant they are to work with, how quickly they pay, how much income they bring you, and whether you enjoy the work they provide. That will give you a good idea not only of whether you need to part ways with some clients or try to work more with others, it will also clarify what’s important to you.


Yep. It’s painful and really, really boring. Download the stats from your accounting software. As a starting point, I would suggest looking at:

  • Profit & Loss statement
  • Income per service
  • Outgoings by category

Note the gap between your income and profit – are you comfortable with that, or is there room for improvement?

Where exactly is your money going (in my case, on a million subscriptions to software)? Is there room to cut down on your expenses?

Look at your income and make a note of which services bring you the most money. Are some of your service offerings perhaps not worth continuing, while others could be expanded?

Human Resources

As a freelancer, your key (and only!) staff member is yourself. This is the chance to do some reflection about how to make yourself the happiest and most productive.

Things to think about:

  • Your work/life balance
  • Where and when you work the best
  • Self-care: being self-employed means you make the rules! Schedule in exercise, family time, whatever makes you be the best “you”
  • What about your work makes you feel great, and what do you dislike? Could some of those less enjoyable tasks perhaps be outsourced?

This will also raise questions about what direction you ultimately want your business to head in .  Do you want to grow into a full agency with staff? Would you prefer to stay solo and bring on subcontractors for particular tasks or projects? I’ve recently been reading Company of One, and realised that I had unintentionally bought into the mindset that growth is the ultimate goal. With some reflection, I’ve now realised I don’t want staff, or endless growth. I’d rather have a smaller number of clients who I enjoy working with and who appreciate my work. Of course money is important, but I don’t want to get to the stage where I have to employ an army of people to fulfil projects. You may well be different, and of course that’s totally ok!


Again, look at the stats: study how many leads have you got over the last year, and how many converted into sales. Look for patterns. You might find that some types of leads tend to fall through, while others succeed. Can you draw any conclusions?

Examine where are your leads coming from and note the success of each channel:

  1. Referrals from existing clients
  2. Personal networking
  3. SEO
  4. Paid advertising

Brainstorm ways you can improve your existing marketing efforts. It might be that your message or even your audience needs to be better defined, or perhaps your collateral (including your website) needs to be better optimised. If one channel disappeared, would all your leads also disappear?

Apparently this is the life of a freelancer, according to a stock image search


Think about your business processes and how they could be improved and made more efficient. For instance, you might find yourself repeating a small task over and over, that could be eliminated with a simple automation. Could you perhaps improve a process with a form on your website? Or having some canned responses to save yourself time?

Is your current software lineup working for you? Make a note of all the systems and processes that need some work.

Final steps

Of course, the magic happens when you use your insights to make concrete changes. For each of the sessions, write your responses and thoughts (briefly) with  3-5 goals. Each goal must have a timeframe – you’ll be reflecting on these next year!

I hope that I’ve inspired you to take the time to hold your own freelance retreat, or at least take some time out to work on your business. 





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