10 min read

How to outsource as a solopreneur

This is the exact process I've used to outsource work and "duplicate" myself for increased profit and productivity.
How to outsource as a solopreneur

When you've been working on growing your business for a while, you'll start to dial in your systems and processes.

For example, when I was working as a freelance copywriter I knew...

  • How many cold outreaches I needed to send to land a client.
  • How many leads a new piece of content + promotion could generate in a month.
  • What I had to do to turn X% of those leads into customers.  

You start to see patterns in all of this which will allow you to create simple checklist like approaches to repetitive tasks.  

When you can pretty much take tasks on autopilot, it's time to stop doing them yourself.

When you have that process defined and down to an art, it's time to bring in a contractor and outsource the work.

This will allow you to maintain that level of output and result all while investing a fraction of your time an effort.

The process I’m going to run you through below is the same process I’ve used to…

  • Grow my own freelance business to 5-figure months
  • Outsource a lot of the time consuming, but ultimately unprofitable, actions (like email list building)
  • Build teams of writers for clients

The process for each one was the same.

The only differentiator here is that we’re doing this specifically through UpWork to find a virtual assistant to help take low profit jobs off your hands.

However, if you get to a point where this is too much writing work to do, you can use the same underlying process to hire your first outsourced writer.

Identify what it is you want to outsource

OK, so generally speaking you’re gonna want to outsource anything that falls into one of the below categories.

  1. The bits you don’t enjoy
  2. The bits you’re not really good at
  3. Low profit (take up time you could spend doing higher paying work - as a copywriter, for me that’s design work)
  4. The bits that are key to your business, but aren’t the best use of your time (like email list building of potential leads)


It might seem a little weird for many. I know a tonne of freelancers who think they can and should do it all.

However, that’s not the way to do this.

Take me for example.

I was a copywriter and my speciality was writing sales copy. As a copywriter, I can bill $500 per hour.

And yet, even as a freelance copywriter, I can use Canva to create pretty decent images.

However, it’ll take me 1-2 hours to create a really high quality image. That’s - at a minimum - $500 of my time.

Now, I could outsource that same image to a pro designer who would bang it out in 20-30 minutes. They might charge me somewhere in the region of $100 for the image.

If I now fill that hour of doing the image with paid work, I’m $400 up.

That’s what a lot of freelancers don’t understand.

Outsourcing work isn’t an admission that you’re terrible at the job or a failure. Outsourcing the right things can be a boost to your profit.

They can relieve stress, increase profits, and end up with a better work product at the end.

You’re running a business. And you need to look at everything through a lens of profit generated.

If you want to hit the 6-figure freelance copywriting business level, you need to outsource the elements that are eating into your photo margins.

This is, by no means, an exhaustive list. However, these are a few of the things I’ve outsourced over the years to great effect.

  1. Any kind of client sourcing and list building (I pay for my VA to do this every month - for a small fee I get 100-150 clients to cold pitch and it takes me 20 minutes of instruction time),
  2. Design work - cause designers are obviously better at design than I am,
  3. Writing work - for when my plate becomes too full or I simply don’t fancy doing it.

The only thing I’m yet to outsource are strategy work and sales calls as I kinda enjoy them both a little too much.

Regardless of what I’m outsourcing -copywriting work, admin stuff, strategy, design - or where I’m finding a service provider, the process is the same.

The process for effective outsourcing

After years of trial and error, this is the basic process I’ve settled on for outsourcing work.

  1. Put a general call out to a specific group of people with a very specific action
  2. Let that call out gain responses
  3. Check the responses for that specific action and, if they don’t take it, deny them immediately
  4. Choose the 3 best
  5. Give each one a very small, paid project to test their skills
  6. Make a note of things like the ease to work with them, the work product’s quality, and their turnaround
  7. Choose the best and award them the whole project as a final test (paid, of course)
  8. If the whole project is good, you have your VA. If it’s not, you pick one of the other two hopefuls and give them the paid project test

I’m going to run you through the actual process on UpWork.

To do this, you’ll need to sign up for an UpWork client account.

Finding an assistant on UpWork

On the home page dashboard, click on the big green button saying “post a job”.

For this, you’re only gonna need to set up a short term contract. So on the next screen, click on the short-term or part-time option.

On the next page, you’re gonna need to give your job a title.

Keep this simple. My go-to is always the below formula.

[ACTION] for [DIFFERENTIATOR 1] to [DIFFERENTIATOR 2]

So, for example, in the SaaS content marketer example, that might be…

Email list building of SaaS CMOs for cold pitching

The job category will then come up, and you should choose the category that best fits your goal.

In this case, it’s lead gen.

On the next page, you’ll need to outline your job’s details.

And this is key here. You need to make it simple.

Like, so simple an idiot child could understand it.

We want to cut out the people at this stage who apply thinking the job is something else.

Much like writing good copy, a simple outline will service you well here.

I usually lead with a quick single sentence of what’s needed.

Then a couple of bullets of the key experience and understanding they should have.

Then I explain in more detail what it is I need and explain, in detail, what the end product should look like.

Finally I ask a specific question.  Something that makes it obvious that they are taking the time to treat the job seriously and not just firing off dozens of applications to any open job.

I usually ask them to include a mention of something in their cover letter.  Something specific, maybe a word, phrase, or piece of information about themselves.

We’ll use this later to sort the wheat from the chaff.

Basically, bad service providers will either completely ignore this and not answer it (showing you they’re not gonna follow instruction) or they’ll put down the bare minimum info.

On the next page, you’ll have to select what kind of project this is. For now, it’s a one time project.

Below that, you’ll get to select a screening question.

This is up to you. It can help remove lower quality people, but often they’ll just put a single word answer.  If you do decide to add one in, just make sure the question is simple enough to be answered quickly but detailed enough to show they’re taking it seriously.

Choose one of the predetermined Qs and then move on.

Below the screening questions, you’ll see an option for a cover letter.

I recommend you definitely ask for one, especially with the area of the job description asking them to provide a small piece of information.

The next page is a multiple choice page for the expertise, skills, and experience level of the service provider you want.

Choose whatever is most relevant to you and your job.

Next is the location. The default will be your home country. But you also have the option of worldwide.

I recommend going with worldwide.

The next page is a little more detail about the number of people you need and who you would like to apply.

On this page, be sure to click “anyone” and “more than one freelancer” Then, add “3” to the box of the number of freelancers you need.

The penultimate page is the budget page.

Only you know what you want to pay for this. Just make sure you don’t obliterate your profit margins.

I usually recommend going with project pricing over hourly.

However, for the initial test, hourly might be better for something like list building.

You can then see how effective each worker is in one hour to help you make your decision.

Then go through and choose your budget and time expectations.

Once that’s done, go through the review page and submit everything to set it live on UpWork.

Once it’s live, you should wait 24-48 hours for it to collect applications.

Choosing your top 3 freelancers

With the applications coming in, you now have to sort through them.

The first thing you want to do is go through the cover letters to see if they added in that simple thing you requested in the job description.

If they haven’t added it, it’s a sign that they don’t read instructions and won’t be a good service provider.

So ditch them.

That will, sadly, cut about 50% of the people who applied.

Out of the ones who are left, go through and read their applications.

There are no hard rules for this, however, I recommend you look for people who…

  • You like from what they’ve told you
  • Have relevant experience
  • Are at the more experienced end of the freelance spectrum on UpWork (newbies can be harder to train)
  • Are individuals and not agencies (as they’re easier to train)
  • Have a decent number of hours and dollars earned on UpWork

Go through and pick 3 of the best.

Explain to these 3 people that you’re going to offer them a short, paid trial to see how you gel as a team.

Detail what the trial will be in terms of deliverables, time, and budget for each one. Answer any Qs they might have and, when they’re happy, award them the job and movie on to the next step.

Giving your assistants everything they need to do a good job

The goal here is to see which of these 3 potentials will be the best addition to your business.

You need to give them everything they need to get the job done.

That means a little up front work from you.

If you’re having them build a list, make sure they have access to the softwares needed and a Google Sheet that’s pre-populated with the column info you need.

If it’s blog writing, make sure they know where to research and have a template to work from.

The more you can do in terms of frameworks for them, the better job they’ll do for you and the less time you’ll have to spend finding workers and editing their work.

Then, you’re going to use Loom to record yourself actually doing the task yourself.

This is going to be their “onboarding guidebook” if you like. It’s going to show them exactly what you need them to do and how to do it.

You’re basically removing any change of miscommunication here.

Record yourself doing the task and send it to the 3 people. Ask if they have any Qs, answer if they do, then let them do the work.

Send everything they need over to them, and then let them do the work.

Choosing your winner

Once you’ve received everyone’s work, it’s time to pick the winner.

You want to look at what they all turn in and make a decision based on a number of factors.

  1. The work product’s quality - cause if it’s crap, you’re not gonna be able to use it
  2. How well they followed instruction
  3. Did they go above and beyond / add anything that improved the product beyond what you expected?
  4. How easy they were to work with

None of these things is more important than the others.

Someone who does great work but is a pain to work with will just give you more headaches than it’s worth.

A nice person who turns in bad work is equally bad for your freelance business’s growth.

Analyse all of the submissions and choose who it is you want to work with based on the 4 criteria above.

Then, award that person the whole contract to complete the entire task.

If after they’ve done that task all is well, then you’ve found your VA.

If they fall short, you have the other 2 finalists to choose from and give a shot to.

This is the process I’ve used time and time again to outsource work and grow teams.

The beauty of this process is it’s based on results, not a gut feeling or samples that can’t be proven.

It’s simple, effective, and helps you find the perfect person to partner with to grow your business.