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Outsource Your Weaknesses To Run A Happier and Healthier Business

Wandering Aimfully Through Running A Business

Outsource Your Weaknesses To Run A Happier and Healthier Business

By confronting and outsourcing your weaknesses, you free up time for things you’re better at.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Wouldn’t you rather focus on doing things you’re happier doing? Things you are able to provide more value with? It’s time to start outsourcing your weaknesses.

A few questions to think about:

1. What is the total time every day you spend on tasks you don’t enjoy and/or don’t excel at? Go ahead, guess.

2. How many of those tasks could be offloaded to someone who can do them better and faster than you?

3. How much is an hour of your time worth to you?


Find Out What To Outsource By Using The Time Journal of Happiness

I have a very simple exercise for you. I want you to create a time journal and log the hours that you spend on two types of tasks:

  1. Tasks you loathe
  2. Tasks you don’t mind, but are slow and/or mediocre at

So, don’t log everything—I don’t care how much time you took for lunch, or that you spent three hours styling your mustache because you love it and lost track of time. Just record the tasks in those two categories above. You can do this manually in a journal, or you can use a free tool like Toggl to keep track.

Your Time Journal of Happiness should look something like this:

9:15 – 9:30: Call with Wells Fargo
10:45 – 11:45: Editing an article/blog/podcast
12:50 – 1:30: Mess with WordPress plugins for email capture
3:20 – 3:35: Entering receipts into your budgeting software

The following tasks of doom tend to pop up on a lot of business owners’ lists (they certainly show up on mine):

– accounting
– bookkeeping
– paying bills/expenses
– customer service
– design
– development
– overall website management
– scheduling
– writing/editing

Find what you need to outsource by acknowledging your “Ugh” tasks

Once you’ve spent a few days recording the hours you spend on terrible tasks, two things are going to happen: one, you’re going to be really motivated to reclaim some hours in your day, and two, you’re going to rank the entries in your Time Journal of Happiness in descending order of “Ugh.” The tasks you hate the most go at the top; the things that are more “meh, I guess I can do this” go at the bottom.

Example Ugh item for me: Anything involving paperwork or bookkeeping
Example Meh item for me: Scheduling items on my calendar

And then, hey, look at that! Give yourself a round of applause because you now have a solid, personalized, prioritized list of things you should and can outsource right now.

The journal entries you outsource should quickly bring you happiness!

Who do you outsource your weaknesses and ugh/meh tasks to?

One entrepreneur’s “Ugh” is another’s Christmas morning.

For every task you hate, there are people and businesses out there who specialize in it, love it, and will take pride in it on your behalf. But where do you find them? Easy. You ask people you know who run efficient businesses.

Who do you know who runs a business efficiently (and probably happily)? If no one comes to mind, look through your email inbox or scroll through your social media feeds. Identify 3-5 people you can email for a recommendation, or start with one person who can introduce you to others.

Do a little outreach to your existing contacts

Write a short and simple email to these efficient and happy business owners. Ask them this simple question:

I’m looking to outsource some of my business tasks. Do you know anyone who can help out with <insert Ugh items from your list>?

There are two beautiful things about contacting these business owners: one, you’re probably going to get back a list of trusted people who can handle your Ugh items. Two, even if they don’t know anyone, you’re probably going to get some ideas from them about running a business more efficiently and happily.

Getting a trusted reference is the gold standard when it comes to outsourcing tasks.

Not only is this a person who comes with a recommendation and experience, but you might also get a “friends and family” pricing discount. Yay for saving money!

Once you get a few introductions, give those folks some trial tasks

There’s a reason you want to reach out to 3-5 different business owners to get references. You want to have a few people vying for the opportunity to work with you so you can find the best fit.

Outsourcing your weaknesses needs to free up your time, not add additional stress if the person you outsource to doesn’t gel with you.

The types of tasks you’re going to outsource are usually in industries where the people are familiar with trial periods or test engagements. When I started working with my new structural editor, Chantel (who you’ll learn more about in a minute), she edited one article for me as a test. It was a great way to see her style in action, and for me to know if the relationship was going to be a good fit.

You should be willing to pay for someone’s time with outsourced work, AND they should be willing to work through a test/trial period to make sure the relationship will work for both of you.


Do You Have Doubts About Outsourcing?

You may be concerned that spending the time to outsource your weaknesses will take more time than just doing those tasks yourself. Well, I’d disagree with you. I’d also like to bring up an important point I learned a few years ago.

Are you hurting your business by trying to save money and delivering a less-than-stellar experience for your customers?

Just a few years ago, I was starting to write a lot more articles for different media outlets (Entrepreneur, Inc. Magazine, etc). All was great, except I was having trouble finishing articles and meeting deadlines. I finally sat down and asked myself, “What am I really worried about that’s keeping me from finishing these damn articles?”

Through a bit of introspection, I realized that it wasn’t the act of writing the articles that scared me. It was that I was nervous people would find my grammar mistakes. I knew I wasn’t an accomplished writer (or even someone who took a single writing class, ever), and I was worried that people would see that in my writing and judge me for it. So what did I do? I reached out to a friend who was an accomplished writer and asked if they ever had the same thoughts I was having. That friend emailed wrote back, “That’s exactly why I hired a copyeditor. I let them worry about the grammar, punctuation, etc., and it removes my attachment to that part of the writing process.” This was exactly what I needed to hear. I asked them for an introduction to their copyeditor and used her services immediately for my next article. She corrected a bunch of errors and delivered a completed article. And you know what? Submitting that article felt different than submitting any other article before. I felt more proud of it. I felt like the fears that scared me about putting my writing out into the world had been vanquished. That copyedit cost me $30.

How much is it worth to you to completely alleviate a fear of doing something? $30? $100? More? I pay that amount of money (and more) to multiple people who help me run my business more efficiently and with less hesitation.

The more time you spend feeling insecure about the different facets of your business, the less time you have to deliver a great experience to your customers.

My outsourcing secret weapons I’d like to share with you

I’d like to save some of you a step or two in your quest for outsourcing your weaknesses. Below, you’ll find a list of people and services I use, trust, and love. These are my personal recommendations*, but I’d absolutely make sure you set up a trial period if you plan to reach out to any of them.

*I am not being compensated for any of these recommendations and am not getting any referrals commissions if you use these folks. Just trying to share great people with you!

Bookkeeping: Shelley Leveridge from FoldedOwl

I hate bookkeeping. I just don’t like it. It’s a task I can do, but I’d rather use the hours it takes on many other things, like flossing. Luckily, I have Shelley from FoldedOwl.

I pay Shelley on a monthly basis, and she keeps track of my business expenses and helps me get all my documents ready for tax filing. But that’s not all Shelley can handle. She also helps renew annual business filings and random organizational business tasks I don’t enjoy doing.

Structural Editing/Writing: Chantel Hamilton from Afterwords Communications

I mentioned Chantel earlier, and I’m so glad I have her in my outsourcing arsenal. Not only is she a fantastically nice human being, but she’s also helped me make my writing process insanely more efficient. She’s a structural editor, which means she helps get a piece of writing from the idea or rough draft stage to finished product.

I have probably 20 articles being written at any given time. Some I write in one sitting, and some take months. When I feel particularly stuck, I know I can reach out to Chantel. She’ll work her magic to take an article from “I think I need to trash this” to “Whoa, did I write that!?” That’s how you know you’ve found a great editor.

Design: Roland Mangahas

I’m a designer by trade. I have a degree in design. My first job and business were in the field of design. But I’ve realized that I haven’t kept up with honing my design skills, and that other folks can do it much quicker than I can.

I used Roland’s talents for IWearYourShirt, BuyMyLastName, and SponsorMyBook. I think I’ve recommended him to over 100 people over the years. He’s reliable, fast, affordable, and always willing to make sure I’m happy with the work he does (no matter what). And like most talented designers, he doesn’t even have a portfolio. Ha!

If you have the slightest inkling that you need some design help, reach out to Roland immediately. He’s happy to pass along work examples and give you quick price quotes.


This is actually the only company on my list of recommendations. I’ve used Chop-Chop for multiple projects of varying sizes over the years. They got their start as a PSD-to-HTML development shop, but they can do a whole bunch more these days. Whether you need help turning a design into a WordPress site, or you just have some nagging issues with your current website, they can help. Super fast and affordable.

Legal Stuff: Ruth Carter from Venjuris

Not all lawyers are blood-sucking vampires! Some of them own basset hounds, do improv comedy, and like going on road trips to talk about entrepreneurship and becoming a lawyer. That’s Ruth Carter.

I’ve used Ruth’s legal prowess on a few of my projects. She’s helped me write a few legally binding Terms & Conditions. She’s helped me establish business entities. And she can help with loads of other legal stuff (depending on the state you live in). And if you don’t live in a state where Ruth can help you? My guess is that she can recommend you to a lawyer in a state that can.


Outsource Your Weaknesses Wrap-Up

I don’t advocate running a fully outsourced business. That’s not the point of this article. The point is to find the areas in your business where you are currently spending time (our most valuable, non-renewable resource), and where I believe you can exchange small amounts of money to get that time back.

The next time you wonder if you should outsource something, ask yourself one important question:

Do I want to spend my time doing this Ugh or Meh task, or do I want to spend it delighting a customer or increasing the revenue of my business?

That one single thought has greatly changed my perspective on trying to do everything on my own. I outsource my weaknesses to people who specialize in getting those tasks done so that I can focus on things I do best.

What do you want to spend your time doing?

Outsource Your Weaknesses To Run A Happier and Healthier Business

(Big Fat Takeaway)

You should be outsourcing your weaknesses so you can spend more time on the things you actually enjoy doing and let other people accomplish tasks for you that you're not great at.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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