I used to a strong advocate of outsourcing everything that could be done cheaper by somebody else and used to push others to do the same. Below are the steps I consider now, and why.

I spent a lot of time trying to figure out what my time is worth so that I can easily decide what I should do myself and what I should outsource, because it would be cheaper.

If you want to do these calculations, you can search for numerous methods online, one good one that I found is: Calculating the Value of Time: How Much is Your Time Really Worth?

After I calculated what I felt my time is worth, I started to decide what I should or shouldn’t be doing myself. For example, should I put my own tracker together when my time is worth, say, $100/h or get somebody else to develop it for $20/h? Financially it makes more sense to get somebody else to do it, BUT then I started to consider the following:

• What else would I be doing with my time?: If I got somebody else to do it, would I be making $100/h, or would I be procrastinating on something and not making anything. There is the option to spend more time with family of friends which is worth a whole lot more than $100/h… but do they have the extra free time to spend with you? 
• Sometimes there’s more to the work than the output: The thought process that goes along with the setting up of the tracker is worth a lot more than the $75 “saving” and cannot be outsourced. So I would be either losing out on the thinking and in the long term losing a lot more on a sub-standard tracker or would be spending the same amount of my time thinking about the tracker as it would take me to build it myself, meaning that I would be paying more for the tracker (the $25 for the tracker development and the $100 for my time to think about what is needed).
• What if I enjoy doing it?: What if I enjoy putting the tracker together and find it stimulating and/or relaxing. I may want to do this rather than watch a movie to relax. 

This highlighted to me that deciding what to outsource, is more than just the financial consideration. Don’t get me wrong, I strongly advocate outsourcing and think it is critical in any business or personal success, but I consider the following now as well:

1. Prioritise: How important is this activity? How urgent is it? Should it be eliminated, automated or delegated. Look up Eisenhower’s Urgent/Important principle and the Focus Funnel for further prioritisation principles… 
2. Scenario: Is this a once off activity or recurring? What thinking behind this activity is required and can (or should) it be outsourced? How much joy would I get out of completing this task?
3. Resources: Do you have the right resources to complete the task or would it take longer to find the right resources than it would to complete a once off task, for example?
4. Optimise (Minimise/Simplify):  If it is an activity to be outsourced, can it be reduced or simplified? Can it be integrated into something else? Can other important things also be included?

I also find that sometimes I will outsource work even if I am paying more than my time is worth, this could be for a number of reasons, including: the quality would be so much better if somebody else did it, or there were legal implications so I cannot do it, or I just really don’t want to do it, etc

Now, I:

• don’t spend a lot of my valuable time calculating what my time is worth anymore,
• consider the 4 aspects above before outsourcing, and
• don’t push others to outsource as much because I don’t know their priorities or scenarios. I will ask the question whether it is something that can be outsourced, and leave the decision up to them.