Saying ‘yes’ (or ‘no’)

By 15th March 2018Uncategorised

Tomorrow marks three years since I started freelancing.  It has been an amazing experience: I love the sense of freedom that working for yourself creates and the buzz I get when I win a project, and I’m grateful that I have finally achieved a good work life balance.

But having that freedom means I’ve needed to learn a new skill: I’ve had to get smarter about deciding what to say yes to, and when to say no.  I’ve had lots of different opportunities over the last three years, and I’d like to share five questions I ask myself when deciding where to focus my time:

  • Will doing this generate income? As a freelancer if I don’t work, I don’t get paid, so opportunities that are going to generate income move to the top of the list.  I ask myself this question on a regular basis.
  • Will doing this increase the probability that I’ll generate income in the future? I’m learning to play the long game and so if a task will add to my skillset, increase my credibility, or develop my network then it may well be a good thing to do, even if I don’t get paid now.
  • Will I enjoy doing it? One privilege of being my own boss is the freedom to do things that I enjoy and which make me feel that I am making a difference.  It is nice to be able to decide without checking in with someone else.
  • Will doing this cause me unwanted stress? I went freelance partly to improve my quality of life, and I’ve turned down some lucrative work in the past because I felt the stress levels would outweigh the income.  That’s a hard thing to do, but I try to remind myself why I did this in the first place.
  • If I say ‘yes’ to this, what do I have to say ‘no’ to? I find this question helps me clarify the concept of lost opportunities.  I found it very easy to agree to everything when I started, but I only have a limited amount of time and I’m trying to be smarter about how I use it.

If you are thinking about freelancing then I hope these questions might help you.  I’ve learned a lot in the last three years, so please do get in touch if you’d like to chat about what it is like outside the bubble of regular employment.


  • Tim Meldrum says:

    HI Gary, great post! And I think you’ve acquired some real wisdom there. At the risk of sounding pious, we have another question on our list which overlaps with both your ‘enjoying’ and ‘stress’ questions: does the work fit with our values? If it doesn’t but we take it for the money anyway, we’ll quickly cease to enjoy it, and it will cause us stress almost from the start. Just say ‘no’ … All the best, Tim

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