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“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

7 years later, and I can now boast about how I haven’t pulled an all-nighter in 5 years.

In fact, I haven’t worked past 5pm in 3 years.  And most workdays start at 9:30.

What gives?

I Tidied Up My Freelance Biz.

Tidy Definitions:

Verb: bring order to; arrange neatly.

Adjective: (of an amount, especially of money) considerable.

Adjective: arranged neatly and in order.

Alt. (as in, “I’m a freelancer, and I need to tidy up my business.”): getting your act together, getting real, dropping the stuff that doesn’t matter, and focusing on things that do!


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

You’ve gotta find your cause and go get it!

And in the meantime, tidy up that mess you call your business!

Action #1: 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 #2: Convert An Existing Service Into a Product

Products have boundaries and rules.

Humans understand products intuitively.

But humans don’t understand services.

Action #3: 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 #4: Stop Selling WordPress Maintenance.  Just Stop It.

Action #5: 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 #6: 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 #7: 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 #8: 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 #9: 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 #10: 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 #11: 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 #12: 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 #13: 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 #14: 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 #15: 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.]

Contrary to popular belief, Google Docs is a better project management tool than Trello, Basecamp, Asana combined!  In fact, those other tools lend themselves to agitation.

The biggest problems you need to solve are the ones your unique and specialness created for yourself. As in:

  • 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 #16: 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 #17: 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 #18: 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 #19: Pay Yourself a W2 Salary

If I came to you and told you, “I have a job for you.  It has no benefits.  No salary.  No vacation time.”

Would you accept that job?

If you did accept it, would you respect yourself?

Respect Yourself.

  1. Pay yourself a salary. 
  2. Plan and take unplugged vacation days. 
  3. Give yourself permission to be a shitty employee every now and then.

You’d do it if you worked at the University.

Why don’t you respect yourself when you run your own business.

Paying yourself a salary has a number of benefits:

  1. It’s consistent income you can count on.
  2. It puts you in the mindset of a business owner.
  3. Your spouse takes comfort in what you are providing.
  4. You won’t be stuck with a big tax bill at the end of the year (unless you make a boatload of extra profit!).

Action #20: Niche Down

Action #21: Dump the Paper Checks

Your paper check-based billing is costing you more than you think.

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 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.