100+ Freelancers Later – The Secrets of a Super-Delegator

samfloy~20 July 2020 /Delegation

Mish and her husband Rob have hired over 100+ freelancers since 2012. In this post, they share some of their key lessons for small businesses and freelancers that are just starting to delegate.

Mish’s journey

When Mish and Rob began their delegating journey, they were freelance writers themselves.

“… so we kind of knew the process, we were familiar with how everything worked.”

They had quit their jobs for greater freedom and flexibility. When they reached the point of delegation, they chose to use freelancers over hiring permanent employees because it similarly offered greater freedom and flexibility.

“So Rob and I run a few different small businesses and we don’t want or need the hassle and pressure of having proper staff especially as most of the time we don’t actually need them.

Mish and Rob started slowly with small jobs but after success and applying lessons learnt, their use of freelancers quickly grew.

“And it’s freed up so much time, I can work on the stuff I’m actually good at.”

Eight years, 100+ freelancers, and several successful businesses later, Mish and Rob are still using freelancers.

Upwork is their platform of choice.

They found that they love designers from Eastern Europe and coders and back end workers from the sub-continent. Mish has loved getting to know her freelancers and has worked with many for years.

Why they use freelancers

In addition to the freedom and flexibility, Mish points to the talent available and their relative low cost as the main reasons why they use freelancers.

“We liked the fact that we could work with some really talented people who are on these platforms and don’t necessarily want to work for anyone else, either”.

“… even though you’re not paying them that much, it’s a lot more than they get in their home country.”

Freelancing platforms offer protection

Mish argued that many people are afraid to use freelancers because they are scared of being taken advantage of by strangers. But Mish points to the escrow process that many platforms use which means that freelancers aren’t paid the agreed upon amount until you the client are satisfied. Mish feels secure.

The importance of having a good hiring process

Mish has also learnt that a good hiring process will weed out undesirables. Here are some of her key lessons:

1. Use a detailed job description with clear expectations for the finished product

2. Check freelancers’ reviews over their ratings. Good ratings are easy to give but a great or bad review stands out.

3. Hire someone with a specialist profile that matches the job. Many people with tangential skills apply in hope but are not experts.

4. Check the cover letter. Avoid boilerplate replies and people who have obviously paid little attention to the job description. Use your name in the ad and see if they address you personally in their letter. She no longer uses a question about people’s favourite cheese!

5. Use Upwork’s milestones. Set a small financial milestone for a selected freelancer’s first task so that if it turns out that they don’t meet the grade, the financial loss is minimized.

“Yeah, those [bad] people are around, but there are tonnes of amazing people on there.”


Mish (and her husband Rob) are, in my opinion, a perfect example of people playing into the global trend of distributed teams.

They began offering services as freelance copywriters and over the years have transitioned to running their own projects (The Duff, Property Hub, The Loop etc.) by hiring outsourced help.

“And it’s great to work with all these people from around the world …it’s just really fun. It’s lovely”.

If you have had a similar experience or have other lessons to share about freelancers, please do let us know – we’ll add them to future posts!

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