I'm going to lead this post with a disclaimer: I’m a recovering freelancer.

I’ve built hundreds of small sites for clients, friends, and family over the years. Friends of mine are freelancers. And I’ve hired dozens of freelancers over the years while running development teams here at Bowtie.co and other companies. I genuinely appreciate the impact that freelance work has had on our industry. The ability to find talented designers, developers, and consultants for short term or as-needed work has created phenomenal efficiency in our industry over the last several years.

And here is the ‘but’...  All that said, as implied by the title of this post I am of the opinion that many - if not most - small businesses should be extremely cautious or reluctant to hire freelancers depending on their specific needs of your company and customers.

If your website or application is the backbone of a significant amount of business revenue, you should not hire a freelance developer, upworker, or your CMO’s nephew to run point. Wondering if you are in that boat? Here is a simple litmus test - would you delegate any other business critical task on the same order to that person?


Having the foresight and wisdom to pick the right sized partner will help you avoid these common narratives (as told by our clients):

  • “We’ve been working with our freelancer for awhile now and had some good results, but now we can’t get ahold of them/don’t trust their output/aren’t seeing the same results...”

  • “We had to switch developers and they keep rebuilding what we have before starting the new thing” or even

  • “We had a new developer look at our code and say it was in bad shape, and now we need to pay 3X as much as we expected to get this new feature out”.

Knowing when to delegate is a critical skill for any entrepreneur, I’d argue it’s equally critical to know who to delegate to. Choosing the right partner for the job can make or break your goals.

Start with a gut check. Does it make sense to go cheap, or hire for speed, redundancy, longevity, and reputation? Would you hire your hobby mechanic neighbor to help change your oil? Probably. Do you want that same person rebuilding your brake system the week before a family road trip?

If you are struggling to get your first website built, you are confident in your ability to evaluate the work first hand, or you have an uncertain business model - perhaps a freelancer is the right sized parter. If you’re concerned about speed, quality, long term stability, technical debt, and 24hr uptime, it’s likely time to consider an Agency.

But wait - aren’t Agencies really expensive?? Not necessarily. Yes, it’s true you often get what you pay for, and it’s worth spending a little extra on your tech budget to have a better partner. But, you don’t need to go broke working with a digital agency, or software development company. You may save hundreds of dollars hiring a random freelancer - but can you ensure the quality of the work? Who can back that person up in a crisis? And what assurance do you have that they won’t slow down mid-project or jump ship completely?

Agencies solve these problems inherently, and are used to evaluating problems and creating new solutions at a rapid clip. But, just like any other team member, not every Agency is created equal. Look for a value-oriented Agency partners who enjoy their work, offer transparency with time and tasks, and are willing to listen to your needs and recommend less expensive solutions to solve them when it makes the most sense. Most importantly, never work with an Agency partner who treats what they build for you as a black box. It’s your site/software/IP; you should own it from day one, and it’s the responsibility of any reputable agency partner to  ensure you understand the value of their work as much as they do.

If you like the sound of that Agency experience, you might want to consider working with Bowtie. We’re frequently told we’re not like other web agencies, and our clients enjoy the way we do business. Want to kick the tires a bit more? Check out our portfolio, pricing, and services page then give us a call or email us if you like what you see.