Weighing the Decision of Learning vs. Delegating as a Solopreneur

If you’ve only been a solopreneur for two minutes, you already know one thing to be true:

When you’re a one woman shop, you’re typically wearing no less than 10 hats. 

From creating the actual *thing* your business sells, whether that’s jewelry, websites, or monthly P&L reports for clients, to also being the…

  • The marketer/copywriter/photographer
  • The designer 
  • The bookkeeper
  • The operations director 
  • The customer support manager 
  • The coffee fetcher 

Need we go on?

It’s a lot to learn, and let’s be honest, no matter how much of a college try you give, some things will just never be in your wheelhouse. 

It can leave you wondering...should I really go this whole thing alone?

Here’s the thing about the conversation around solopreneurship that, we’ll be real, kind of irks us… 

Just because you’re a solopreneur, doesn’t mean you have to work completely by yourself.  

You don’t need to hire a team, unless you want to. And you don’t need to do all the things in your business, unless you want to. 

The key is knowing the implications between learning vs. delegating, and understanding how to leverage both sides of the equation so that you’re using your time, resources, and energy wisely so you can reach your goals of solopreneur success without sliding into burnout or falling out of love with your business. 

Here are the top four questions we ask when considering whether to learn a new skill so that we can do it ourselves, or enlist the help of someone who can completely take the task off our plate. 

Question 1 ) Does learning this new skill benefit your overall business acumen and/or allow for better delegation?

“You don’t know what you don’t know.”

I feel like this saying was the defining mantra of my first five years as a solopreneur, and the only way I can think to relay the concept of this question is with my personal experience around building my Facebook advertising skills. 

When I first got into the Ads Manager (at the time, Power Editor), the primary “F” word out of my mouth wasn’t Facebook, and I quickly swore I was going to hire an ads manager to prevent myself from hurling my laptop off my 4-story balcony. 

After some deeper Googling and YouTubing, I figured it out and got my first campaign off the ground and, of course, felt like an accomplished advertiser. (As if I didn’t have a toddler-esque meltdown an hour earlier.)

The first step was the hardest, and a couple of things quickly became clear:

1 - There was A LOT more to learn 

2 - There was A LOT of potential through this advertising channel 

There was no shortage of ads managers to hire or programs to take, but I opted to go with investing in a course that would teach me what I needed to put together a strong ads strategy and develop compelling creative because those were two skills that would benefit me not just in the long-term in my own business, but also with the work I did for my clients, even though I wasn’t specifically doing Facebook ads for them. 

Furthermore, with the immense potential to either gain a significant return on my investment in ads, or flush all my marketing budget down the drain, it felt important to have a solid understanding in this area of business so that whenever I would delegate this task out, I would be able to adequately see the big picture, ask the right questions, and ultimately, understand the outcomes to see if I was actually getting good results. 

At the point in time when I was considering whether to learn Facebook ads or delegate it, learning felt like the necessary pathway whether I was planning to have help in that area the next week or in the next year. 

So, with that example in mind, when deciding whether to learn the skill so you can complete the task at hand, or outsource someone to do it for you, the first question exists as a way to get you to think in terms of the big-picture of your business to weigh the benefits and opportunity costs of learning vs. delegating. 

Question 2 ) What will allow for the greatest return on my investment? 

Seemingly a simple and obvious question, but when you begin to weigh in the investment of some courses and programs versus the investment of having a done-for-you delegated solution, it can feel like a no-brainer to go with the lower-cost option, especially if you’re a starting solopreneur who’s bootstrapping their efforts. 

Sometimes the course is less expensive, sometimes it’s the hired help, and that’s why the prior question is the one we ask first because building your overall business skillset can provide a greater ROI, even if the process of learning takes longer than getting someone else to do the work for you in the immediate moment.

On the flip side, you may look at a particular skill, do the research on what would be involved to learn that skill, and have the intuition that this isn’t a skillset you’re meant to take on, and the responsibility needs to be handed off. 

Finding the answer to this question can be part number-crunching, part intuition, but the important thing, is to get specific with the numbers and, again, look long-term when tapping into your gut instinct.  

Question 3 ) What’s my timeframe? Will learning the skill versus delegating bring the return on investment more quickly? 

We already alluded to it, but the option to learn a skill yourself versus hiring someone else to do it can run along different timelines, and one timeline might work better for you and your business to see that return on your investment.

The key to answering this question is realistically examining how much time you have to devote to learning a new skill, finding and training a new person, or adding in the task to your own list of business to-dos. 

Now, one thing we want to point out that we know can be the plight of the solopreneur is the thought, “it’s just easier if I do it myself because I know I’ll get it done right and the way I want.”

This is a story you’re telling yourself, and one that might be seriously hindering the growth of your business. 

Back to my Facebook ads example, that decision wasn’t made out of fear that someone else would do it wrong. 

Instead, learning the skillset myself would not only allow me to gain a greater return on my investment for the stage of business I was in at the time, but would also serve as a bridge for me to find the right person to take on the task for me eventually (once my time and available bandwidth became shorter and shorter). 

If it’s the fear of the time it will take you to communicate and relay expectations to someone you hire, the key thing you need here is systems

Systems allow you to have a documented process in place that communicates the outcome you’re looking to achieve and/or how you go about achieving the outcome, and serves as a starting point to keep your work streamlined (if you’re completing the work yourself), or as a place to start for anyone you’re delegating to. 

Side note: anyone you’re outsourcing to and who has a deeper knowledge of the skill you’re hiring for should be able to help you improve the system and its outcomes. 

To go deeper on systems for your solo biz, click here to get in on our free mini course where we’ll walk you through the four systems every solopreneur needs to succeed, suggestions for getting them up and running, as well as top recommended tools to help you regain more time and sanity. 

Question 4 ) Is this skill something I have the desire to learn?

Now that you’ve looked big-picture, weighed out all the costs and benefits, crunched numbers and examined your timeline, you might still be left thinking, “I would rather pull out every single one of my eyelashes one-by-one than do this.”

Something that you dread doing that much will likely result in the task taking up more of your time and energy than it should, which inevitably translates to monetary cost and loss down the line. 

However, we also want to add the caveat that it’s not unheard of to not like something you don’t feel you’re good at, but we’re also rarely ever good at a new skill on the first try.

And while there will always be tasks and projects we’re not as excited to do within our businesses, if it’s truly something you hate doing or that causes your momentum to come to a halt, you have to consider what that’s costing you and either decide to:

- Ditch and delete that effort altogether (or at least put it on the back burner). 


- Delegate it out. 

Don’t downplay your intuition and your gut. If you’ve done the work to make informed and data-driven decisions, you have to trust yourself enough to know whether you’re making a choice based on the information you have available or out of fear/procrastination/perfection, or any of the other emotional roadblocks we come up against as business owners. 

When all is said and done, and all questions have been considered, our hope is that you’ll be able to move forward with clarity around learning new skills to enhance and further your business or offloading some of the “doing” from your plate and wearing one less hat, so you can focus on the tasks you truly love doing and bring you a greater return in less time. 

And as a final note, we’ll add this: never underestimate your ability to do hard things you’ve never done before, and don’t undercut the value of your time and personal sanity. 

leave a comment

Leave a Reply

Your email address will not be published. Required fields are marked *

© One Woman Shop, LLC | 2021 | Privacy Policy and Terms of Service