Tips for Triumphing over Tough Tasks

executive coaching productivity tips Sep 07, 2023

If we’re to believe social media/the internet, then when we find our “true calling”, when we follow our “real passion”, when we’re “fully aligned”, running our own business our way, there will be no such thing as work.

It’s all going to be bliss, successes and an embarrassment of riches.

I’m just going to go ahead and pop that little balloon.

Running a business should be mostly amazing, fulfilling moments. And, unfortunately, there will always be parts that just plain suck.

No matter how aligned and fulfilled and joyful and all the things the work is for you, there will always be parts that are just plain draining.

So what could entrepreneurs do when they are faced with tasks that they find incredibly draining?

See if anything can be responsibly delegated

The first thing is to see if there's anything that can be responsibly delegated.

Obviously, if there's something that you truly dislike doing that can be delegated, then that would be wonderful. But there are times when you really can't delegate. And there are times when you just think that you truly can't delegate.

And when we are not sure, or we're so overwhelmed that we're having trouble seeing one for the other, take a moment to talk to an assistant or someone else. If there's someone that you trust a lot on your team or if you have an amazing assistant, talk to them for some perspective. They may be able to recognize that this thing that you think you can't delegate, well, this portion, can. So try that. See what happens.

And maybe somebody else can help point that out, especially if you have maybe developers on your team or somebody who's really strong with software. They may be able to point out what can be automated. There are many tools, software out there that automate tasks, streamline repetitive tasks, and we're not always on top of what is out there. There's so much out there, and it seems like every day I hear about this new thing that does this new automation thing. That's great, but I don't have time to spend researching all these things. So if you have someone in your network or on your team whose job it is to stay on top of those things, talk to them.

They may point out that using this plugin your task that took 11 hours is now going to take you two. I've actually seen something along those lines that was done through custom coding. If you're doing this task repeatedly, it might be worth the investment and the little bit of time to look into that. It might even just reduce the time to the point where it feels less draining. Because if you're looking at this task that you really dislike and it takes, let's say 11 hours as in my example, well, if you can do it in two hours, then that's going to make it a lot less draining.

You may have noticed that at the beginning, I said responsibly delegate. Again, because there are some tasks that really shouldn't be delegated. Bottom line is if you're an entrepreneur, you need to keep an appropriate pulse on your business. And there is that risk that if you delegate too much, you may not know what's going on in your own business. And that could lead to making strategic decisions that are actually detrimental to the organization. So make sure that you are not overly delegating. I know I've also seen books that essentially suggest you should be delegating everything that you do. If that’s your leadership philosophy, go for it. It's just that it’s not part of my leadership philosophy. I'm more of a transformational leader. And if you're going to be an impactful, transformational leader, well, you need to be around. Everybody has their own journey, so you do you, I'll do me and that works for us. As this is my own philosophy, I think that there are some things that really shouldn't be delegated that you really need to stay on top of what's going on in your business.

Let's say, in this instance, you absolutely cannot delegate that task, but it is absolutely dreadful. Every second spent on it feels like an hour. Ask yourself: “Can you co-work with someone?” I've seen this work extremely well, just having someone there can help. Like in the example I'm thinking of, this person was just dreading doing this thing, but it was necessary that they did it.

Just having the other person there – even though they too were working – was helpful. Every now and again they would say: “Hey, I'm really stuck on this thing. Could you give me a little bit of perspective on this?” They talked for five minutes, got unstuck, and continued on. A couple of sessions later and it was done. So if you're in that kind of situation, think about co-working with someone on your team. Maybe there's another leader that is in a similar position.

Break up the draining tasks

If the tasks are really large, it can feel overwhelming. And you're just looking at this thing that you really don't like doing that's going to take forever. And that's really not motivating you.

That’s when I'll try to break those tasks into small manageable steps. Then, I celebrate the progress as I complete one part. It might be motivating to have the smaller steps in a visible place where you can “scratch” them off. You could write them on a chalkboard. And mark them as done as you go. That might feel good.

I'm one of those people who likes checking things off. If you're that kind of person as well, then maybe that might help.

Another aspect of breaking it down into smaller chunks is getting through it with a timer. If it's really, really draining, first of all, close all other apps and tabs, and focus for whatever amount of time makes sense for you. Let's say you set a timer for 20 minutes and just get it moving. I know the reason I close everything to focus is because I know that all of a sudden I “remember” that I really “should” be returning that phone call. Or I “realize” that I haven't looked into that particular grant for our product. And “I should do that right now.” Or “I should be reviewing this particular thing.” To help ensure you spend those 20 minutes on that one thing, keep open only what you truly need.

The reason I like 20 minutes when it's something I really dread is because it doesn't seem so long. Normally, when I set a timer, it’s for 50 minutes and then a 10 minute break. Otherwise, I find the working period to be too short. But if it's something I really dislike, 50 minutes feels long. But 20 minutes gets me going. And sometimes I find that once I'm going it's not that bad, and I'll keep going. And when you get to, let's say your 10 minutes of rest, using my example, reward yourself with something, any little thing that you can do to re-energize yourself in that time. Maybe you re-energize yourself by listening to a song you really like or by taking a brief walk around, whatever you feel like. Get up and clear your mind.

Try to change your mindset about it

A difficult – but doable – one is trying to change your mindset about it. Even if it’s temporary. Let's say it's something that you really, really don't like. I'm not saying try to suddenly find them magical and wonderful. No. But if you can temporarily trick yourself into finding them less dreary, then it can help.

And one of the tricks is to define:

a clear goal for each of the tasks,
the desired outcome,
a clear sense of purpose.

Ask yourself: “Why am I doing this? What are the consequences of me not doing them? What impact is it going to have on revenue and/or people?”

For me, it’s compliance. Compliance is one of the worst things for me. Some people love it, which is great. I'm not one of them. When I have to fill out those forms, they're long and especially when they “improve” them. The last time I did one, it was just terrible. It was supposedly improved and it took me about three times as long because I couldn't figure out what they meant. Some of the options didn't work like they used to. It was version one of this new “improvement”. I had some feedback, let's just say. So when you're doing that and you get a sense of why you're doing this, for example compliance, well if I don't do it, the organization's going to get fined. It's not going to be good for the organization and we're going to be spending more money on this thing. So no thank you. If there are some reasons that can be like, “Okay, I really recognize the importance of doing this, let's just get it over with.” that can help change the mindset for a brief time. I'm not saying you're going to love it, but it helps in making them a tad bit less draining because you recognize just how important this task is.

Something else that I find helpful is to try to make it feel different. Maybe do the work elsewhere. For example, when I really, really dread something, sometimes a change of scenery makes it feel less draining. And it can be moving to a different workspace, adjusting the lighting, putting on some background music. It can help motivate you a little bit and make it feel less draining. In terms of changing workspaces, it doesn't have to be necessarily going to the coffee shop but it can just be going outside. Changing the environment can help. Sure, it doesn't make the task fun. Let's not exaggerate here, but it can help make it okay. Another approach can be to combine a draining task with something that you enjoy such as listening to music. It could be a desk treadmill or cycle, a sitting ball or a favorite decoration in sight. Having something pleasant to look at can make you smile. And so maybe having something like that also kind of changes how you feel because it's also tapping into something that makes you smile while you're doing something that really doesn't make you smile.

Setting realistic expectations

In my experience, I’ve found that there is an unrealistic expectation that every day is going to be enjoyable when we’re in “the right place”. And that’s causing a lot more unhappiness than necessary.

There will be some parts that we dislike immensely and dread when those tasks come around. But the sooner we get rid of them, the sooner we get to move on to something we actually enjoy.

Try various strategies and see what works for you in getting those draining tasks checked off as done.