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Setting Goals Like a Boss #WinningLife (and a worksheet)

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Happy New Year! ?

I declared January to be Organization Month on the blog and we’re kicking things off with a different type of organizing. Today, we’re going to be talking about setting goals.

I hope you didn’t stay up too late last night partying and feel rotten today. Been there, done that and I’ve spent more than a few nights sleeping on the bathroom floor because it’s easier that way. ? Luckily, I’m all grown up and super mature now. (cue hysterical laughter from anyone who knows me).

But seriously, when I look back at what my life was like 10 years ago and compare it to where I am today, I almost can’t believe it. In the last 10 years, I got divorced, bought my first house, got a graduate degree, became a grandma (twice!), became a saw and hammer-wielding DIY badass, changed career paths and started this blog with Alex. Whew, that’s a lot of stuff!

One of the big things I learned along the way was that in order to succeed in any measurable way, setting goals for yourself is critical. In my post last week about this month’s organization focus, I said that if I don’t set specific goals for myself I tend to drift. Not drift off the path. I mean drift from day to day without any real intention or purpose. Before I know it, the year is past and I don’t have one significant thing I can point to and say “I did that!” Which gets me feeling all

setting goals

Maybe it’s because I’m getting older but I get frustrated with what I perceive to be wasted time. I want to feel like I’m moving towards something, even if I’m not actively doing something every minute of every day, ya know? Setting goals for the year will allow me to focus my attention and energy on the plan I’ve set to achieve those goals. And they aren’t always huge goals either. It could be something as simple as “Read 20 books”.

So why does everyone wanna talk about goals every year?

Because if you do it right, setting goals will actually help you get where you want to go in life.

And it doesn’t matter how old you are, or what your financial situation might be, or how down-on-your-luck you might feel. Anyone can set goals for themselves and be a winner. I’m going to repeat that one more time for emphasis – anyone can set goals for themselves and be a winner. Because I believe in you, faceless person on the Internet, whoever and wherever (and maybe whenever you are, because I can’t completely rule out time travel?).

Alright, last week I asked you think of a few goals for yourself. If you missed that post or didn’t do it, that’s fine. Just think of one now. I’ll wait.


*Still waiting*

*Staring, willing you to hurry up and think of a damn goal*

OK, ready? Good. When I first sit down to map out my goals, I usually try to keep to keep it simple. I’ll either have one big, monster goal (like a buying a house) or (more commonly) 2 or 3 bigger goals and then 3 or 4 smaller ones.  How do you choose which goals you should be setting?  That really depends on where you want to go. There’s a quote that I heard recently that’s really stuck with me.

“Unsuccessful people make decisions based on current situations. Successful people make decisions based on where they want to be.” -Benjamin Hardy

So what exactly does that mean? Well, to me it means that the truly successful people are in it for the long game. They’re willing to make sacrifices today for the big payoff tomorrow.

Consumer debt in this country is at historic highs. And that’s directly connected to the “I want it now” mentality that’s so pervasive in today’s society. People are willing to basically mortgage their futures for the newest tech, or the fancy car, or whatever. They’re not thinking 5 minutes into the future, let alone 5 years.

When you’re setting goals for yourself, try to look 5 years into your future. I don’t mean wrap your winter scarf around your head like a turban and peer into a crystal ball. I mean, try to answer that most difficult of interview questions. “Where do you see yourself in 5 years?” Ugh. I always hated that question. I thought it was stupid because things change, right? There’s no way to tell what you’ll be doing.


The reason they ask that question is that they want to see if you’re the kind of person who lives in the moment or if you have the ability to set and achieve goals. Going back to our quote above, maybe they’re trying to determine if you’re going to be successful or unsuccessful. Damn, those sneaky bastards.

Now, think about your goals again.

Try to imagine what you want your life to look like in 5 years. And try not to focus on only the material aspects. It’s fine if you want a bigger house but you might want to reexamine if you’re thinking you want to live in a McMansion. Think about what’s truly going to bring you satisfaction and peace in your life. Christmas is recently over but let’s not forget the lesson of Scrooge, ya’ll. He had all the money in the world and not a damn thing else. We saw how that turned out for him.

Once you’ve decided on your goals (or at least one for now), it’s time to map out a plan to achieve it! This is the fun part to me. It’s taking it from just a dream to a PLAN OF ACTION.

We’re going to take those goals and break them down into manageable parts. This is not groundbreaking information. Pretty much every book, blog post, magazine article, skywriter, you name it, is going to tell you the same thing.

“We’re going to tackle the whole thing all at once and it’s going to be glorious! Said no one ever.”

Let’s Make an Action Plan!

When I’m first documenting my action plan, I’ll take each goal and make it the top level. Then I’ll determine a handful of action items that need to be done to accomplish the main goal. Then I’ll break those action items down further into tasks, and if I feel I need to I’ll break those tasks down too. I’ll break it down into as many pieces as I need to in order to feel like it’s manageable and workable. We don’t want to set ourselves up for failure right at the beginning so take the time to really think about this.

I’m old school, so I like to write things down initially. Later on, I’ll add it to an app. Maybe that’s double the work but I need to SEE it before I know if it’s going to work. Wouldn’t you know it, I have a handy little printable to use for this too.

setting goals

At the top is where the primary goal will go, and then below that all the tasks and subtasks. Everything should have a due date because it helps with accountability.

Here’s an Example

One of my real goals for this year is to make $1000 from the blog. In the top box, I would write, “This year, I want to monetize the blog and make $1000”. And I would be saying this in my mind in the voice of Dr. Evil but maybe that’s just me. I’ve decided on several courses of action to help accomplish that goal. I don’t want to spoil any surprises so I’ll keep it general for our example.

One way to make money is through the use of ads on the site. One of my boxes below could then be “Increase ad income”. Another way to make money is through affiliate income so that would be my 2nd box. The third box could be a product that I could sell.

OK, great. Now what? Well, now we have to figure out the tasks we need to complete in order to complete the subtask, which in turn completes the main goal. Got it? Good.

In order to increase ad income, I’ll need to increase traffic to the site. I could join link parties, Facebook groups, and Tailwind/Boardbooster tribes in order to get my content in front of more eyes. I could also look for more ways to promote by developing a Pinterest strategy, and scheduling posts to my social media channels. These would all be the lowest level tasks. I could even break it down further into daily or weekly tasks. Whatever works for you is the best way to do it.

How Do I know when I’m Done?

The most important part of setting goals is having a way to quantify it so you know when it’s complete. A goal like “I don’t want my life to suck” is difficult to measure. “I want to make $1000” is easy to measure. Just keep track of how much money you make. “I want to buy a house”. When you sign the 8 million papers at closing, that one is done too.

I hope this post inspires you to think about your future and things you can do to make it a reality. I really, really, believe in setting goals. There’s no way I could have accomplished the things I’ve done in my life without goals and a clear plan of action for completing them.

If you’re looking for a little more guidance, The Simple Elephant planner (affiliate link) is designed to help you conceptualize and achieve your goals.

And if you’d like to download my printable to use in your goal setting, enter your email below!

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