Very often, this is the first question I get from entrepreneurs  who are new to remote help is:  How do I know when I should outsource?

For those getting to know me, I worked with small businesses to resolve issues as a mediator. I tend to ‘hear’ a bit more. In this case, I hear this question as two distinct questions:

  1. How do I know I’m ready to outsource?
  2. How do I know what types of things to outsource?

Both great questions that on the surface look very simple to answer, but are worth thinking about in a deeper way.

I define outsourcing as ‘asking for help in your business’ while delegating is ‘telling that person specifically how to help you’. That’s not terribly complicated, is it? You do that all the time in your work as a nurse, or as a parent or spouse.


Am I ready? and How will I know? These are the most constant questions for an entrepreneur. We visit these questions again and again over time because the answer changes.

Sometimes I think that being in business is like driving your car into a parking garage. Specifically, I’m thinking of the municipal lot in downtown Boston

A concrete behemoth with a circular ramp at its core, this was my secret garage, where with a bit of luck and strategy I regularly scored the cheapest parking.

At each level you had to stop and decide to turn left and go down or turn right and go up. (Left meant a shorter walk down but more time spent looking for a space. Right meant a longer walk down but more empty parking spaces.) I usually opted to go right.

You’ll face similar questions and choices in your biz. Outsourcing is a right turn strategic move.

It might take you a minute to figure out how to make outsourcing work for you, but when you do, you’ll have many opportunities to choose from and no real competitors around to get in the way. Not that I believe in competition. This is no competition when you are on your path and not comparing yourself to others.

You are ready to delegate the minute you decided to start your business. There’s no rule that says you have to do everything yourself.  Except the one you made up.

Anything that is outside of your genius zone is a project someone else can do.  If it requires your personality, vision or expertise, it’s all yours. Otherwise, ask someone outside of your business to help you achieve that.

Here’s where I mention food.  Do you have a comfort food? Something that when you eat it you feel safe, warm and satisfied?  At the moment, my comfort food is ramen.  We also have comfort tasks. Things we do when we want to feel like we are working, want to calm down or be distracted.  My comfort task is research. I find it thrilling and very satisfying to ‘find’ the right answer. Comfort tasks are the first place to start to ask others to help you.

You might be saying something like,’with what money’, right about now.  I’m gonna be blunt with you. That is an excuse. It’s one of the three lies all entrepreneurs tell. There is help available for you no matter what your budget.  With the number of on-demand workplaces online now there is someone waiting to work within your budget and happy to do it. You’ve heard of Fiverr, right? Prices start at $5-10 for administrative and other work.  I’ve had great success with it and another platform, Upwork.

You’ll know it’s time to bring on teammates into your nurse business when:

  • you’re constantly behind & stressed
  • people tell you to get help
  • you’re missing out on good stuff
  • the question occurs to you

Sometimes you just need to hear it from an neutral source. If that’s you, let me hear what’s going on and give you my thoughts during a free consultation.

If you’re already outsourcing…woo hoo, doing my happy dance.  Tell us about your first project so we can all learn.



Dina Lynch Eisenberg, JD, is the CEO of, an outsourcing training/consulting firm for successful lawyers and entrepreneurs based in Oakland, CA.

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