21 Ideas To Create More Profit in Your Freelance Business

“Leave me alone!” I yelled at nobody in particular.

It was 2am, and I was looking at my Macbook screen on my kitchen table, infant daughter and wife sleeping comfortably in the adjacent room.

“Why am I doing this?” I asked myself. 

It was my 3rd all-nighter in as many weeks.

“Why do I keep putting myself in this horrible situation?!” I asked myself incredulously. 

I knew the answer the whole time.  It was staring me in the face.

Me holding my daughter while taking a businss call, 2011

Victory & the Ongoing Battle

8 years later, and I can now boast about how I haven’t pulled an all-nighter in 6 years.

In fact, it’s a rare day when I clock in after 5pm.

What gives?

We ain’t kids on the playground no more – We are grown-ass adults, friends!

Time is precious – you’ve gotta figure out why you get out of bed in the morning and go get it!

Action #1: Pay Yourself First

It took me 5 years to treat my business like the profit-making machine it needs to be, the solution is simple. Whether you use a complex system like Profit First, cut yourself a check once per month, or pay a nominal fee to Paychex to have them cut yourself a check every month like I do, the best thing you can do for yourself is to pay yourself a steady wage.

The solution is simple – pay yourself the same amount every month from your business checking to your personal checking account. Why the same amount? Because that’s how you build a strong business and life! You need to be able to count on a specific amount of money every month to make plans! If your business income isn’t steady enough to pay you a specific amount every month, then either it needs to build up a reserve to smooth out the rough months, or it needs to close.

Paying yourself a salary has a number of benefits:

  1. It’s consistent income you can count on.
  2. You can start planning for the future – vacations, retirement, etc.
  3. It puts you in the mindset of a business owner.
  4. Your spouse takes comfort in what you are providing.

Action #2: Outsource Something Significant.

When you outsource something, you are prioritizing.  You are building an important business-owner skillset.  You are building capacity.  You are freeing your time.  You are making money on someone else’s time!

Unless you are being paid to, literally, be present at a desk, you absolutely need to outsource something.

Freelancers outsource to other freelancers all the time!

Here’s the friggin How To Outsource To Freelancers blueprint for cripes-sake!  And here’s an article about How To Outsource WordPress Development, specifically.

What significant thing that is on your plate right now can you outsource to someone else?

Can’t think of anything?  Trust me, it’s there.

Action #3: Run an 80/20 Analysis on Past Customers

Once per year, I run an 80/20 analysis on all of my current and former customers.

I am curious to learn which customers are a great fit and why. 

Then I reposition my products and pitches to get more of the good and less of the bad.

Some outcomes for me have been:

Action #4: Double Your Productivity by Blocking Off Time

It’s a little-known thing that effectiveness and efficiency can be at odds with each other. 

If you are effective, but not efficient, that’s not the end of the world.

But if you are efficient but ineffective, the world is crumbling around you.

Here’s 1 simple tactic that has doubled my productivity.


  1. Write down what the most important thing is for you: the thing that if you get it done, you’ll feel great about your day.
  2. Block off 90 minutes at your peak time to do that one thing.  Uninterrupted.   Turn off your damn phone!  Turn off those stupid real-time notifications on your computer.  
    Learn how to properly use Slack…

Action #5: Ask for the $$$ on the First Call

It’s 4 years since I last met a potential customer in person. Most of my deals close during the initial 15-30 minute phone call. These are warm leads, mind you, being people who are asking specifically for WordPress support in most cases, but they are unreferred and don’t know me from a hole in the ground. Usually they found me in a Google search.

A freelancer that doesn’t close deals rapidly is wasting time & money. Countless times I’ve been able to close WordPress development, maintenance, support, and/or training deals on the first call, without ever meeting in person, after 15 minutes. When people are ready to buy, they’re ready to buy. Why make them wait?

I have a friend who meets all his customers in person before they buy. Usually they don’t buy, because he’s trained them that his time is not valuable – they just got a free 2-hour meeting after all. They think, “Why would I pay for something I just got for free?”

Here’s how to ask for the money on the first call. Don’t. make it unnecessarily hard on yourself like this guy.

Action #6: Be Brave.  Take Risks.  Get Fired.

When’s the last time you were fired by a customer?  (or it’s annoying, passive-aggressive, freelancer equivalent: “not been re-hired”)

My business gets stronger when I get fired.

When I get fired, I get curious.  I ask, “Why did you fire me?” 

It’s a brave, fair, honest response.  And I learn a lot from those conversations.  Stuff that helps my business get more anti-fragile.

Every small risk you take makes you more resilient to taking risks.

So go out there and toe the line of comfort.  Then take one step forward.  Don’t leap.  Just inch forward into the forest of discomfort.

Before my first rock show with The Corrupt Senators back in 1996, I was literally pissing. I was in the bathroom of The Wonder Bar in Twin Lakes, WI, and I couldn’t stop peeing.

Postcard of The Wonder Bar, Twin Lakes, WI. 
(Where I peed for an hour before taking the stage.)

I mean, I’d stop peeing for a minute and then I’d have the urge to pee again.

That’s called, stagefright.

I went out there and played the show.

It was horrible and exhilarating at the same time.

I was scared to death.

But I gained strength from the experience. 

I hadn’t died.

I was still standing.

Now, some hundreds of performances later, I experience very little stagefright before taking the stage.

Action #7: Stop Using Technology & Software To Solve Business Problems.

Technology and the new new thing thing is exciting, but it won’t help at all in solving your very real business problems.

Slack by itself won’t help your team get better at communicating (it’ll make your deficiencies worse).  [Learn how I use Slack on WordPress dev projects.]

Basecamp, Asana, & Trello are nice project management tools, but I’ll take a good project manager with pen, paper, & phone in hand every time over any of those tech tools. Great work happens in spite of technology, not because of it.

And often those very basic tech tools are overkill, anyway! Contrary to popular belief, Google Docs is a better project management tool than Trello, Basecamp, Asana, etc, which tend to foster more agitation than results.

The biggest problems you need to solve are the ones your specialness created for yourself:

  • Why the hell are you pricing your product so low? 
  • Why do you care about beautiful code when your buyers don’t?
  • Why is your close rate so low?
  • Why are you having trouble collecting on that invoice?
  • Why are you giving that away for free?
  • Why aren’t you doing more marketing?
  • Why do you get in the middle of every single communication between your dev team and the customer?

Action #8: Convert An Existing Service Into a Product

Products have boundaries and rules.

Humans understand products intuitively.

But humans don’t understand services.

Action #9: Stop Consuming Content.  Start Creating It.

There are 2 types of business owners:

  1. Those that create content.
  2. Those that consume content.

The people that consume content are always the ones paying.

The people that create content are always the ones getting paid.

Consuming content is usually a complete waste of time.

Read why I created a free beginner WordPress by Email training course as part of my content-creation strategy.

Action #10: Stop Selling WordPress Maintenance.  Just Stop It.

For some reason, people who support WordPress sites are selling “WordPress maintenance” all of a sudden. But most small businesses who would buy their service would never in a million years pay for “WordPress maintenance.” Would you?

You know what people will buy, though? Unlimited WordPress support. That’s what. Things like adding photos, updating your Contact page, securing your SEO, etc. Those might all be bullet points on your WordPress maintenance page (but let’s be honest here…probably not), but they need to be the product, not the feature.

When I bought a car recently, their strongest pitch was for “Unlimited Cleaning” of the interior of the car – something that the car does not need but that tugs at my heartstrings. I almost bought that expensive cleaning package. But car maintenance? No thanks, dude – I’ll press my luck with the beater you just sold me!

Action #11: Upsell an Existing Customer

You are giving away too much.

Now that you’ve productized your offering, you are ready to upsell!

If you offer a WordPress training product, ask them if they also want to buy your ongoing WordPress maintenance product.

The hardest hurdle here is the ask.  There’s no way around it – just ask!

Action #12: Write down your bucket list.

Before you can conquer the World, you need to know thineself.  

What gets you excited?  What makes you want to stay up late to get that little extra thing done?  What are you striving for that will help you stay focused on the goal while doing that annoying thing that your customer just asked?

You need a bucket list.

Action #13: Get Curious & Write down why you work.

It’s easy to float through life and work reacting to things.

But if you want to get what you want out of life, you’ve first got to figure out what it is, exactly that you want to get.

Get it?

Action #14: Use a script for sales emails and phone calls.

Scripts save you time and make your sales process even better.  

See my real-life phone and email sales scripts.

Action #15: Use Slack intentionally.

Slack is probably the #1 time-waster and most-ineffective way you’ll use your time today.

Want to get effective and efficient with your time?  Step 1: Distinguish between the use cases for real-time vs. asynchronous communication.

tldr;  If you wouldn’t call someone on the phone for it, don’t send it via Slack!  Consider not sending it at all!

Here’s how we use Slack.

p.s. I say, “Slack”, but you can replace that with any real-time tool that interrupts you such as:

  • Github push notifications.
  • Google hangouts.
  • Facebook push notifications.
  • SMS messages on your phone.
  • Email alerts on your phone.
  • etc. etc. etc.  If you receive an interruption notification, it better be an emergency!

Action #16: Use Email Intentionally.

See above.

Email is better than Slack for 99% of use cases.

Unless, of course, you are using it wrong.

Agitated companies are the biggest abusers of our trust in email.

I work with an agitated company where there will be 5 people copied on emails.

“Why is the CEO copied on this password reset email?” I ask.

Shrugs all around.

It’s really confusing to me.

Emails should be 1-to-1 conversations.

If there’s more than one person on an email thread, you either have a trust problem, a communication problem, a worker problem, or a workflow problem.  (but it’s probably a trust problem)

Action #17: Upsell an Existing Customer

You are giving away too much.

Now that you’ve productized your offering, you are ready to upsell!

If you offer a WordPress training product, ask them if they also want to buy your ongoing WordPress maintenance product.

The hardest hurdle here is the ask.  There’s no way around it – just ask!

Action #18: Don’t Respond to RFPs.

No matter how much pressure you are feeling,  Never Respond to an RFP.

Unless the RFP meets these 2 simple criterion.

Action #19: Get Clear About Whether You Are an Artist, Architect, or Craftsperson.

Most freelancers I talk to have no clue what they are.

“I really like writing the code and designing the website and building scalable business solutions!” 

my friend recently told me.

Ummm…  You can’t do all that and run your business and do your taxes and do your bookkeeping and do your sales and do your marketing and etc. etc. etc.

Which one do you like best?

Are you an artist, architect, or craftsperson?

Action #20: Write Down Your Assumptions About People & Business

Here are some assumptions I make on a daily basis about my buyers:

  • They care more about communication than whatever product they are asking me to build/deliver for them.
  • They want valuable stuff and are willing to pay a premium for it.
  • They will pay more for a trustworthy product.
  • My relationship with them does not add value to the products I’m selling, but it might keep them around longer.
  • I, me, personally, the royal “I” add a ton of business value to products and projects, and I don’t come cheap.
  • They want someone with my experience and perspective about business & technology.
  • They want someone who will help them get closer to their goals and are willing to pay a premium for shortcuts.

Are yours different from mine?  Why? How? Who is right?  Who is wrong?  Let’s debate!

We learn and grow only by challenging our assumptions.

Every now and then, life throws us a surprise curveball that forces us to challenge our assumptions. 

A death of someone close to us, a surprise firing of our spouse, a surprise loss of a valuable customer, etc.

Those things often force us to grow in amazing ways that push us forward in unexpected ways.

Those are usually painful moments.

So too are those turning point moments where we grow our business.

For me, a big turning point was a few years back when I fired all 8 of my employees.

It was painful at the time and still is painful

But that experience has helped my business grow in ways that I couldn’t have predicted.

What Makes You Unique?

It took me a decade into my biz and 5 years of actively-searching for answers before I discovered my unique value propoition and what I’m seeking in business.

Action #21: Niche Down

“Yes, we do that,” I said even though I would have to hire another freelancer to write the custom code to build the map widget. “Expanding your offering is what successful businesses do, right?!” Wrong!

Expanding your offering horizontally will reinforce your worst habits. Instead, grow deep roots. Deep roots are secure, immovable, and don’t let you stray too far in any direction. Rather than expand your service offering, decrease it. If you run a WordPress support & maintenance company like I do, say “HELL NO!” to SEO work. Say, “HELL NO!” to logo design. Say, “HELL NO!” to copywriting. Say, “HELL NO!” to…you get the idea.

Get really damn good at delivering that 1 thing you are amazing at and then find more people to buy that one thing! This is how you maximize profits & take vacations.

Action #22: Dump the Paper Checks

Your paper check-based billing is costing you more than you think. Learn how I dumping the paper earned me 3x profit!

If you do nothing else, do these things to leave a bigger positive footprint on the world:

  1. Always strive for more calm.
  2. Choose your customers based on what you want out of business & life.
  3. Read books.
  4. If you don’t know where to start, give me a call.

Significant edits made to this page on April 11, 2019

Significant edits made to this page on Aug 17-24, 2018 in preparation for my WordCamp MSP 2018 talk.

Significant edits made to this page on July 11, 2018 in preparation for Minneapolis-St. Paul WordPress Pros meetup presentation.

Originally referenced in a June 2018 Minneapolis-St. Paul WordPress meetup presentation.

Toby Cryns

Toby Cryns is a freelance CTO and WordPress Guru. He also writes for WPTavern.com.