There is a lot of talk in the entrepreneurial-glorified space about delegating and outsourcing work. And sometimes that makes a lot of sense; if someone else can do the labor of menial tasks--let them.
And often on my consulting calls with clients, I will hear this half-truth surface. "I should hire someone else to do that so I don't have to." or thanks Michael Gerber, "I'm working in my business, I won't be able to work on my business if I keep doing this." What sometimes people don't see is how crucial the task truly is, or the part they are looking to delegate is the 'working on their business' part. I get it if you have a hamburger stand and you are selling hamburgers. You do not need to be the person flipping patties or squirting mustard on the bun.
I often sense this idea, if the task is extremely difficult, time consuming or challenging, it's better to outsource it than burden ourselves with the labor. Please don't misunderstand; some tasks should definitely be outsourced that are difficult. Like accounting for instance. But what I hear tends to be a bunch of tasks that are just 'work' that people somehow feel they are entitled to skip if they find someone else to do it. The 'Tom Sawyer' approach to entrepreneurial life is a fantasy and perhaps a recipe for disaster.
Work is hard. That's just the nature of the beast. But this idea that when we are free from this work we can do other work that's more important, may also be a fantasy. When I ask people more about this supposed free time they will be creating by hiring someone for the job, they perhaps haven't gotten that far in their own head of what they will do next.
"So, you hire this guy to do the work, what will you do then?" Ah. And that's where the lightbulb goes on. They replace work with the idea of something personal. "I'll share more time with my family" or "I'll take up a new hobby." When faced with this question, if your response is something work-oriented, great, perhaps you really should hire someone. If your response is something personal, then you are probably just looking to escape doing the work. This is a key point when you should hire an expert to help make you better at the task, streamline the process, or help you make the work less-cumbersome. Knowing the difference between needing a break and about to break--that's the art of entrepreneurship.
If what you are really seeking is more personal time for family and hobbies, schedule that in now. You don't need to hire someone to achieve that outcome, you just need to manage your time better. Anyone can schedule a 60 minute lunch break with a spouse once a week or create space for a hobby by waking up a little earlier. These outcomes do not need to be hinged on the back of a new hire to escape putting in the work.
Where it gets particularly dangerous is when people need help doing a task but fail to realize it. They have to either learn more to perform the task at a higher level or they need to hire an expert to see them through their struggles. Hiring someone with less experience, skill and understanding is rarely going to make ANY situation better. We often don't consider the amount of time it takes to get a person trained and developed for any given role. McDonalds created Hamburger University for teaching people how to make burgers more productive and in uniform fashion worldwide. But regardless of the time it takes to invest in someone, we sometimes confuse the situation. By hiring someone to do the difficult things we struggle with doing, may temporarily reduce our struggle, but probably not fix the real problem.
Some responsibilities are too intense to outsource. When you secretly wish for a magic genie to come in and do the job better than you in less time, for $14 bucks an hour, know that blaming them when things go wrong may protect your ego, but maybe not your company. Do the work that needs to be done each day. Delegate when you can pass the job through the question, "What would I do with the time I'm saving?" If it's something personal, take a deeper look at the situation. You may need someone with a fresh perspective, rather than a fresh pair of hands for the heavy lifting.