Learning How to Delegate

Learning How to Delegate - picture of man and woman working together

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Asking for help has never been my strong suit. In fact, I’m pretty awful at it. I’ve always been a do-it-yourselfer. Part of it stems from the way I was raised. Part of it is just my personality. And, part of it is because I’m a stingy bastard who would rather spend 15 hours learning a new technique than let any of my hard-earned cash be pried from my cold dead hands.

Of course, the drive and desire to do things on your own can be a great thing. It’s helped us build our own business, allowing us to quit our 9-5 jobs and work for ourselves. This type of mindset is critical for anyone who dreams of entrepreneurship. You have to be willing to take chances, believe in yourself, and trust that you know how to do it better. Unfortunately, once the business grows large enough, this go-it-alone attitude can be an entrepreneur’s greatest hindrance.

For example, lately, I’ve found myself getting bogged down in the tiniest of details. Sure, I could pay somebody to make a media kit for me, but I could also do it myself. Yes, I could outsource a lot of my administrative tasks. But, why should I do that…when I can do it myself?

I’ll tell you why: Because it’s costing me huge amounts of time, energy, and – ultimately – money. Obviously, these tasks all need to be done, but they don’t pay the bills. In fact, they’re taking time and energy away from the projects that actually do make money. In effect, being cheap and doing it all myself is actually costing me money (and happiness) in the end. I need to learn how to delegate.

How to Know When It’s Time to Outsource

Outsourcing and delegating tasks doesn’t have to be just for entrepreneurs. In fact, almost everybody should consider outsourcing something in their lives. Here are a few tips to know when it is time to ask for help.

  1. You’re Feeling Overworked – Do you find yourself working late into the night or throughout the weekend? Maybe you’ve noticed your patience is thin. Perhaps you just can’t get out of bed in the morning. Chances are that you’re working too much. Feeling overworked can cause stress, exhaustion, and other health problems. If you’re feeling overworked, it may be time to look at hiring out some of the things in your life.
  2. You’re Not Able to Focus – Sometimes we’re unable to focus because we’re having a bad day. Other times, it’s because we have too much on our plate. If you’ve been having trouble focusing for a while now, it may be time to consider outsourcing some of your tasks. Determine which things you have to do and which things you can pay others to do for you. By eliminating some of the tasks on your to-do list, you’ll be able to focus on – and complete – the most important tasks at hand. Plus, the quality of your work should improve dramatically.
  3. You Can’t Get Everything Done – Having a to-do list a million miles long is stressful. Even worse is the feeling you get when you fail to complete it. Personally, I struggle with this every day. I tend to put more on my list than I can actually accomplish. I prioritize the things that must get done that day, which means a lot of the side projects never get the attention they deserve. What happens is I move the undone tasks to the next day, stress about it, and then move them to the back of the line behind the must-do’s once again. Every day the side projects pile up higher, causing me focus stress and focus issues while decreasing my productivity. What I should be doing is spending my focus on the things that a) I can’t outsource, b) currently make me money, and c) will make me money in the future. After that, I need to learn to outsource the rest…and so should you;)

Delegating (FTW)

Of course, not everybody has the luxury of being able to outsource tasks, particularly if you’re still paying off debt. However, if you can afford to, learning how to delegate can be essential to growing your wealth and your increasing your overall happiness. Remember, it isn’t a failure to hire somebody to cut the grass, clean the house, or do your taxes. The difference between successful entrepreneurs and those that burn out lays in their ability to delegate. Spending a little bit of money to keep your focus (and your sanity) can free you up to do other things, eliminating a lot of stress and making you a more money in the end.

Now, about that media kit…

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  1. Can I just outsource my life? Kids, job, etc. but I’ll keep the fun stuff. Especially after being overloaded with ideas this weekend. So great to meet you guys!

    1. In all seriousness, there are days when I want to outsource our dishes and laundry! I’ll keep dreaming!
      And yes, great to meet you too!

    2. Ha! No kidding 🙂

      Great to meet you too Mark! Hope your travels home went well.

  2. I have a hard time with this too. Especially if it’s an easy task, it just seems like I should be able to do it. I don’t think I’m yet to the point where it makes sense to hire someone to do these things, but I’m getting close to that point. Good luck!

    1. Thanks Dee! We definitely can’t hire somebody for everything, but we should for some things.

  3. Delegating is not my best skill but something we probably all should pay attention to. I finally hired someone to clean my filthy Windows and I think that’s the best money I’ve spent all year!

    1. We hired somebody to clean our house…and it is the best money we’ve ever spent!

  4. Even if you’re not in a position to delegate (hi, teaching!), these signs apply to asking for help. It seems to me that people often feel if they are going to be pioneers, they have to totally go it alone. This is a great reminder that it’s important to collaborate, too.

    1. Absolutely. These can apply to any situation where you just need some help. Sometimes, we just have to give up a little control over a single situation to gain more control of our lives.

  5. I have a hard time giving up control because I like to do things a certain way and can be super anal about it. But, I’ve realized that as I add more to my plate, delegating has a become a big relief. Even though my budget is small, every little bit helps.

  6. Can I outsource going to the gym? Hahaha. Seriously, though. I know a lot us suffer from trying to do ALL OF THE THINGS. I’m working on be a smarter worker. Great meeting y’all at FinCon, by the way! And congrats again on the Plutus award! 🙂

    1. Ha! I wish I could outsource that 🙂 As you said, sometimes we all just need to work smarter, not harder. Great meeting you as well. I’ll pass the congrats on to Holly 🙂

  7. I have a hard time with this as well – especially getting over the hump of finding someone that will actually work to my standards – that takes time! But in the end, sometimes the money spent is really worth it – to have that time back and just the sanity of one less thing on your to-do list! Thanks for the reminder 🙂

  8. I am so bad at this. I want to do it all. For the first time, I just paid someone to redesign my homepage. Normally, I would do it myself. There comes a time when you have to let go and have someone else do it. “You can’t do everything” is a tough lesson for me!

    1. Right? It is the curse of the entrepreneur! But, I’m finally realizing that outsourcing is the difference between having a job and creating an actual business.

  9. I SO hear you about needing to learn to let go and delegate more. One day, LOL. Although I am starting to get REALLY good at delegating housework to the kids. 🙂

    1. Well, that always helps:) Hopefully we’ll be able to give them a few more chores as they grow. For now, that doesn’t work too well.

  10. My husband is normally a huge DIY guy, but the other day I brought up something to put on his honey-do list, and he said, “You know what be a good use of our money? Having you hire someone else to do it.” He was completely right. When something is futzy and annoying, I would much rather pay someone else to do it (if my husband won’t do it for free).

    1. Yeah, it is definitely nice to have the option to outsource. If you choose the right tasks and the right people, it is usually worth it in the end.

  11. I can relate! I’m fiercely independent and believe we can do everything ourselves, but am slowly learning this is not the case. While not as bad at delegating as I am, my husband tried to roof a portion of our house this summer in an effort to save money… Lesson learned, he does not have roofing as a side hustle in his future… After lots of frustration, that portion of the roof needs to be redone. Wasted time and wasted money. I think he’s starting to learn the “delegate” or “outsource” lesson too…

  12. It’s difficult to let go of control and delegate tasks and projects. It’s something that I struggle with everyday. At the same time, the only way to grow and scale a business is to effectively delegate tasks and authorities. I think the key is making sure you delegate the right tasks to the right people.

  13. I am actually a pretty good delegator. I learned very quickly in my career that I cannot do everything, nor does it make sense for me to even try. I coached many financial advisors on running successful businesses and one of the biggest roadblocks was their inability to delegate. Like you said, when you’re in debt, it may be harder to outsource tasks since you’re trying to curb expenses, but even then, you need to think big picture. If paying someone to clean your house bi-weekly frees you up to earn more, than you should at least consider it or how much you need to earn to make it work.

    1. Yeah, we are quickly learning the value of delegating tasks and asking for help. Heading to the FinCon conference this weekend drove that point home even more. You just can’t do everything and do it exceptionally well.

  14. It can be difficult for frugal minded folks to not do everything themselves. This of course is an attempt to save money and seek perfection. I definitely have suffered from this in the past.

    Today, we outsource the management and repairs of our rental properties, use mechanics for our cars, and on occasion have our house cleaned by a service. That feels like a good fit for us.

    1. Yep. I’m so feakin’ cheap that I’m costing myself money and time! Argh!

  15. I’ve been needing to put together my media kit for my videos (I have one for my blog) forever now. I too face the same challenges, but it does come down to money, but then again, COULD I be making more if I had more free time? It’s sometimes worth the risk to find out.

  16. I am SO type A that it’s very difficult for me to let go and have someone else do things for me, but I hired my first VA about 4 months ago and she has been the greatest investment I think I could ever make. I was initially concerned about giving up control and definitely concerned about giving up money but she is well worth the investment not only for me to be more productive but also for me to have better mental health. 🙂

    1. I am totally going to keep that in mind. I think I’m finally starting to see the value in it.

  17. I’m definitely a do-it-yourselfer, too, haha, but for a slightly different reason. I ascribe to the “if you want something done right, you have to do it yourself” philosophy–yeah, I’m a bit of a perfectionist. However! I also try to be very aware of how I value my time. If it’s going to take me many hours to do something someone else could do quickly and cheaply for me, yeah, I put the value of my time above the value of that small fee. As long as I can double check it was done right! 😛

  18. One advantage of in-sourcing is the skills you learn. However, when that is keeping you from bigger priorities and ultimately causing you to lose money, it’s definitely time to outsource!

  19. I was forced to delegate this late Summer/Fall, and it’s when I hired my second writer. Initially I was outsourcing as I planned on starting my MBA this Fall, but I ended up delaying my MBA because I’m writing a book…another good reason to outsource! “Perfectionist” is definitely how I’d define myself and I have a long way to go with delegating, but it’s essential for my side hustle(s) to succeed!

  20. Kevin Payne says:

    Do you have your media kit available to check out? I’d love to learn what I should have in mine. Thanks for your help.

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