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6 min read

Delegating for Solopreneurs (Took Me Years to Figure It Out)

delegation for solopreneurs

A lot of solopreneurs struggle with the idea of delegating any aspect of their business. But I have a confession to make. I am a solopreneur that has never had any trouble delegating. I am happy to assign a job to someone else.

OK, full confession – I was always happy to delegate certain jobs, but I had a hard time actually letting go. I tended to continue doing a lot of the work that they were supposed to be doing. It was not helpful.

It’s tough for entrepreneurs, and especially solopreneurs, to “let someone else do it”. Yet it is crucial if you want to have the best of all worlds.

How I got over it is interesting. I developed a systematic approach that uses 4 dimensions when thinking through whether a job should be delegated or not. Now, when a job passes my test, I feel comfortable letting go. It’s made solopreneur life a lot better.

Good Solopreneurs Delegate

When it comes to delegating, many solopreneurs mistakenly believe that it’s not an option. They believe that, as solopreneurs, they must do it all. This is not true. Solopreneurs do not have employees, but working with contractors, consultants, and other business service providers are often a must if you are going to make your business into something that can:

  1. Support you
  2. Give you the life you want

Delegating for solopreneurs - the Right Way to do it

Before we talk about which job functions or projects you should delegate, there are best practices that you can employ to ensure that things go as smoothly as possible.

Choose Good People / Companies 

This is one that should go without saying, but someone is hiring the the poorly reviewed companies and people. Check reviews, and references, and do some background digging via LinkedIn. If you know someone that is connected to them, you might get some insights. 

I knew of a company that was ready to hire a guy and someone did a reference check from a person that was not provided as a reference. They got an earful about this guy and didn’t hire him. This was a good move. You can do this too.

Check your references always. If it’s worth delegating, it’s worth delegating to someone good.

Interview the People that Will Work for You, Not Just the Salesperson or the Owner

This one is near and dear to my heart and has gotten me twice in the past few years. I did my due diligence and found companies with solid reviews and references. But there’s more to it.

In one case I interviewed the salesperson of a company that provided virtual assistants. She was great and said the right things. But when I got our actual VA, it was a very different story. He couldn’t follow directions, seemed disinterested, and didn’t do anything the way I asked. We went another route.

Another time, I interviewed the owner of the business that was to provide a service. He was fantastic. But when I got assigned the team that would do the work, it was a different story. Everything was “short path” instead of “do it right”. This did not work out either and I ended up months behind.

Check out the people that will actually do the work.

Make Sure They Have What They Need to Do the Job

Make sure they have the tools and authority to do what is needed. If you hire someone to edit images for you, make sure they have access to Photoshop and not some beginner photo editing tool.

If they need access to some system or person, make sure they have permission to do so. 

Responsibility without authority is a recipe for failure.

Clearly Define What is required

As solopreneurs, we often decide to outsource when we are already drowning. There is a tendency to say “here, take it!” hand it off and go take care of all the fires that are burning. 

But that is not a good idea. 

Instead, stop, focus and then clearly define what you expect from the person or company. Get this in writing in the form of a contract (see Solopreneur Contract Secrets from Top-Tier Attorneys). Make sure they know what you need. The odds of success go way up when this happens and if things don’t go well, you can point at the contract and win the debate.

Spell out the requirements in detail and agree to them in writing.

Set Up a Process for Working Together

Set times for regular meetings to monitor progress and address issues. If you are outsourcing an ongoing business function, these should be a regular calendar event - weekly, bi-weekly, or monthly depending on the job. If it’s a one-off project then it may make more sense to schedule meetings at certain milestones as opposed to a regular calendar event.

If you don’t schedule meetings as part of your outsourcing process, you’ll only have meetings when something goes wrong and it’s a lot harder to fix things after they’re broken than before.

Another benefit is that questions can be saved for the meeting. So instead of getting numerous emails, texts, or Slack messages about things as they come up, they can be covered all at once in your meeting, which means a lot fewer interruptions, which means enhanced productivity.

Have regular meetings scheduled for your outsourced processes and projects.

Deciding What to Outsource

I’ve determined that there are 4 considerations to deciding whether to outsource any given job. The cool thing is that this works regardless of whether it’s an ongoing process or a one-off project. Weirdly, it’s both simple and complex. 

It’s simple because it’s pretty easy to determine how the job scores on each of the 4 dimensions.

It’s complex because each dimension has to be considered when making a final decision.

But it’s one of the best ways I’ve found to be comfortable with delegating and letting go after you do.

Consideration 1: How Important is the Job?

Importance means how important is the function to the core of your business. As you'll see, if a process is important to your business, the most competent person should do it. This can be used as a measure of how much revenue the process generates, if any. But it can also relate to critical things like tax returns, where messing it up can be a big deal.

If it's important and you're the best, you should do it. If you can hire someone better without breaking the bank, that's the way to go.

Consideration 2: Your Skill Relative to a Pro

Next, you need to consider your skill versus a pro. Are you better at it than them? Are they better than you? Are you the same?

Whether or not to outsource something that you are best at will be a function of how important it is. If it's important, you need to do it. If it's not, then a pro makes more sense.

If the pro is better at it, then if it's important, it's probably best to outsource all other things being equal.

Consideration 3:  The Time Commitment Required

Time commitment is a big consideration. For processes that aren't directly generating revenue, the decision to outsource can be a function of how much time the process requires. If it doesn't take much time, it is more likely to be worth doing yourself. If it is time-consuming and not important, then outsourcing makes a lot of sense since your time is better spent generating revenue.

Consideration 4: The Cost for You Versus a Pro

The last consideration is the cost of a pro versus your "opportunity cost". Opportunity cost is how much revenue you won't be able to generate because you are spending time doing this instead. If the pro is cheaper than your time, then that is in favor of hiring the pro. If not, then it leans toward you doing it.

Making a Decision - Putting It All Together

Answering each of the 4 considerations probably wasn’t that difficult for you. But putting them together and making a decision isn’t always quite as straightforward. 


  1. The job is of medium importance
  2. You and the pro both have the same skill level
  3. The time commitment is low 
  4. The cost for you or the pro is the same

It’s not so obvious which way to go.

But if:

  1. The job is of high importance
  2. Your skill level is lower than a pro
  3. The time commitment is high 
  4. The cost of the pro is lower than you

Now it’s a no-brainer, you should definitely outsource.

There are lots of possibilities between a no-brainer and not obvious. In fact, there are 3 X 3 X 3 X 3 = 81 different combinations that can occur in this model, which is a lot. I’ve created a spreadsheet tool that can help you decide based on these 4 considerations. 

You can download it here

Some Secondary Considerations

Sometimes there are mitigating factors that may impact your decisions, particularly when you're getting started, including:

    • You need to conserve funds – if money is tight, outsourcing may not be an option.
    • You don’t have enough work – if you’ve got time to devote that isn’t currently being used, only outsource if you are incapable of doing the job.
    • You love doing it – we’re solopreneurs so we can live life on our own terms. If you love doing it and won’t screw it up too badly, go for it.
  • You aren’t sure of the answers to considerations 1 through 4 above

Final Thoughts

Outsourcing is usually a critical part of building a manageable one-person business. When done right, it solves lots of problems and helps you scale your business and take more control over your life. But when done wrong, it can waste money, time and sometimes alienate customers. Take it seriously and do it carefully.

Like getting the inside scoop on how to be a successful solopreneur? Join our free community of solopreneurs to learn a thing or two, get your questions answered, share knowledge with others, and build your network. 

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