When to stop saying yes.

When to stop saying yes.

Or, the best business lesson that
took me WAY TOO LONG to get.

After building my business after hours for many years I decided it was time to take the plunge and start working for myself full time. That was an incredibly scary step – it felt like all my preparation work didn’t matter, I was going to work for myself and surely I’d have no clients and go broke.

As it turns out, that wasn’t the case and I’m writing this just over 3 years on from that last day of fulltime employment. Anyway, the point of all that is I’m a little way down this road now and I’m enjoying it immensely. If you get the chance, I honestly believe everyone should work for themselves at least once. It’s incredibly freeing, sometimes scary and very often, fun.

What I want to help you avoid is one of the big pitfalls of the self employed. When you start, every single job that comes in feels like life and death and we get in the habit of building our weeks around those jobs. That’s totally natural. We do the jobs urgently and we don’t turn stuff down because – hey, you don’t know where the next job is coming from. The problem is we often set up unrealistic expectations in clients – you know how long that job will take, so you estimate the time and off you go. But here’s the rub, you’ll do both your clients and yourself a big disservice if you keep doing it.

There are a bunch of reasons why this is bad for you and your client, but the main one is that it’ll start to suck the fun out of your work, and if you’re like me, you’re doing what you do because you believe life is too short not to enjoy work.

Here’s what I did, and I now realise is far to common amongst new business people, so please, if you’re going out on your own sometime soon consider this as a cautionary tale. Basically I wasn’t selective enough – I took every single job that came my way because at the heart of all self employed people is a little voice that tells you “you’re a bit phony and you’ll need to finish working for yourself and go back to being a regular person thankyou very much”. So you overcompensate for this worry about failure and you’ll take each and every job that comes through the door, good or bad because you’ve got to make this thing work.

Don’t. You need to stop. You’ll inevitably do what everyone does. You’ll get sick, or your life will change in some way and that workload will go from being hectic to unmanageable in a blink of an eye. If you wait longer, it’ll become an anchor around your neck and it’ll bugger you up quick smart. You may even get to enjoy burnout, which isn’t much chop.

This is super common. So I have a simple tip. When is the right time to stop saying yes? It’s before you start thinking to yourself, “I’m skating on thin ice here – if those two jobs run into each other I’ll be in trouble.” It’s way earlier than “I’m not sure what I’m supposed to be doing this morning because I have so much work to do“.

Begin with saying “I don’t know” or “Let me get back to you on that” and make work planning decisions or commitments in a calm and considered way. Don’t promise things when you’re asked on the phone or in a meeting unless you are absolutely certain you can take care of the job and give it the care it deserves.

The time to stop saying yes is as soon as you don’t have a clear plan for each and every individual job and task you have to do in a day. If you’re not 100% sure what the plan is, and you’re the professional, and you should know, then you’ve said yes too many times.

Let’s all do slightly less, but do it better.


  1. These are lessons that should be taught in design school.

  2. Michael F

    Good stuff. One of the only cliches I like is “under promise and over deliver”.