When is the ‘right time’ to bring on a remote assistant? I believe the ‘right time’ is a myth. Let me tell you why.

Typically, business owners judge when the right time is using 3 key resources: time, money, and stress level. For them, the illustration is as follows:

Time and money is pretty self explanatory. When you start your business there’s more time for strategic thought, since you often have little to no customers. As your business grows, you will naturally gain these customers or clients and your available time will decrease. In regards to stress for the purposes of this illustration: it is ‘low’ when you control your calendar and ‘high’ when your calendar controls you.

Breaking down the thoughts entrepreneurs usually have at these three stages in the graph:


  • WHAT IT LOOKS LIKE: A lot of free time, low stress/low money. Entrepreneur is counting every $, waiting to make a sale which would pay for getting admin support. Doing all admin work themselves. Feels like “there’s not enough work.”
  • WHY START NOW: The entrepreneur usually misses the gifts of time and lower stress during the early stages. At this point , bringing on an assistant using an approach of taking on one or two clear and measurable tasks is the easiest. The entrepreneur has the most mental capacity, due to lower stress, to do a proper/thoughtful hand-off. Having more time also means a higher chance of making the right decision about who will be your assistant partner. It doesn’t have to cost an exorbitant amount of money to get started with an assistant. It’s why I don’t like VA models where clients are locked in to a certain amount of time. Needs change, new efficiencies are found. With ChatterBoss we’re an on-demand and dedicated service which means you can work with your assistant as much or as little as needed, and that’s why we’re the perfect partner to start with at this stage of the process!


  • WHAT IT LOOKS LIKE: There’s some money, some time and some stress.
  • WHY START NOW: Balance between having free time to train an assistant and enough clients not to feel tight about paying for support.
  • WATCH OUT!!!: It’s extremely hard to pinpoint this time. Usually entrepreneurs have trained themselves to do it all on their own, and by the time they get to this stage they decide to keep going for as long as they can. Unfortunately, often until they get to the ‘it’s too late’ stage.


  • WHAT IT LOOKS LIKE: You have resources, no time and lots of stress. Entrepreneur is drowning, things are falling through the cracks, opportunities are missed, prospects fall off, communication gets lost, etc.. If a business owner hasn’t gotten the support they need by the time they get to this stage, it often looks like chaos. There’s no time for anything, and the stress is high because you’re making decisions of which ball to drop first. The lack of business time starts to eat into family/self care time, which further increases stress levels. There’s enough work to do, and enough resources to pay for it but it could be easy at this stage to get stuck in a cycle because of the fear that it will take too long to train an assistant and you won’t have time for it.
  • WHY START NOW: You don’t have time, you’re stressed and you have resources to pay for help!!! Do it! If you’ve gone this far without getting support you definitely have systems already in place, even if they aren’t documented yet (which an assistant will help you do). Training might seem daunting but this is actually a great stage for it, because you have plenty that you’re doing yourself. An assistant can step in to watch you over a series of Zoom calls or prepared Loom videos and start taking things off your plate one by one.
  • WATCH OUT: You are so desperate for help at this point that you might end up choosing the wrong partner to support you, which is costly and painful if you end up having to retrain a new person if the first partner didn’t work out. At this stage it’s also tempting to throw everything at once to your new assistant, but this is a mistake because it leads to errors and chance of miscommunication. Even at a time that you’re so busy, the better approach is to hand things off one at a time.

Ideally we would do everything in our personal and business lives at ‘the right time’. When it comes to getting admin support, tough, that ‘right time’ is wherever you are right now in your entrepreneurial journey because regardless of the stage there is always an administrative burden that should be handled by a professional.

What stage does it feel like you’re at today? Have you fallen victim to waiting until it’s the ‘right time’? If you’re an entrepreneur that is working with a VA, at which stage did you decide to start working with one? How did you get to your decision?

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