How I Set Myself Up for Success Each Month + a Free Monthly Goal Planning Worksheet
Anna Osgoodby Life + Biz :: How I Set Myself Up for Success Each Month + a Free Monthly Goal Planning Worksheet

You guys know I am ALL about accountability and check-ins when it comes to working on goals. I think they are so key for growth and making sure the things we’re working on actually still align with where we want to go. Plus, as cliché as it sounds, it’s important to remember that working on your goals is more about the journey than just the destination. When you decide you want to work on your goals you’ve made a commitment that you’re choosing a life of growth and hese check-ins are so helpful in keeping you on track.

Today I’m going to walk you through the framework that I use each month to look ahead, get intentional and set myself up for success. I’ve also included a free worksheet at the bottom of this blog post if you’d like to give the process a spin for yourself too.

Motto or Word of the Month

This is a pretty popular technique and it’s one I love because it allows me to set a tone for my upcoming month. Sometimes I’ll pick or more energized word or motto like drive, or momentum and other times my focus will be rest or reset. Sometimes a single word doesn’t totally represent my mood so instead, I’ll go with a phrase like “get shit done!” or last month I embraced my inner Kacia Fitzgerald and picked “do the damn thing!”

Top 3 Monthly Goals

While of course, I have bigger goals I’m working towards, I like to narrow things down to the top 3 things I want to get accomplished this month. For me, I’ve found writing down a huge laundry list of goals is the fastest track to failure so I like to only focus on 3 things instead. This allows me to really prioritize, which then carries into my weekly and daily activities.

Reminder of the Bigger Picture

The next section I check-in on, is how my monthly goals and the other things I’m working on support my bigger picture goals. Personally, I like to always have the big picture front and center so I know exactly what I’m working towards. This is a great way to really start to understand how small wins propel us and help us grow over time too.

Habits & Routines

This one is BIG! Habits and routines are really the backbone when it comes to making progress on your goals. That’s because there aren’t a lot of things we can do just a couple of times and hit our goals. So in this section, I’ll identify different habits or routines that I am making a priority for this month. Sometimes this section stays the same month-to-month ( if it’s something I’m continuing to work on) and then other times I’ll introduce something new.

A really valuable tactic when it comes to developing routines and habits is starting small and then piggybacking off of other tasks on things you’re already used to doing. For example, brushing and flossing before bed is a no brainer for me... it’s something I’ve done for years. If I just got some new face moisturizer and using it before bed before has been a struggle before, I may try to put it out next to my toothbrush so that I don’t forget. The stronger your routines and habits get, the more things you can start adding until they all just become things you naturally do.

Distractions I Need to Nix

This one is really important too. We all have the same amount of hours in the day, but the way we prioritize our time makes all the difference in what we accomplish. So if you want to start reading more or start a new workout routine then that time is going to have to come out of somewhere else. In this section, I try and identify different things I want to give LESS attention that month.

Video more your jam? Hit play to hear my message!

Efforts I Made Towards my Goals

Then the last two sections are actually things that I fill in throughout the month. The first is making note of the different efforts I made towards my goals. This one is important for me because there are a lot of goals that are very much long-term goals and I’m not going to actually hit them for awhile. Or things that I need to put in a lot of effort before I’ll see real results. Having this section really helps me acknowledge the efforts I’m making and stay motivated. Another reason I do this is because sometimes life happens and you may be slacking some and realize you’re 3 weeks into the month and you haven’t made any moves that support your goals. Back to that accountability thing!

Wins & Milestones

Last but not least, I keep track of wins or milestones that happen throughout the month. A lot of which I’ll then share on my Instagram check-in updates! These are a step beyond the efforts I’ve made because these are actual results. So for example, if I want to work on my public relations strategy and be featured in the media more, an effort would be pitching x, y, and z publications, whereas a win, would be if I was actually featured in one.

I love this section because it reminds me how much you can really accomplish in one month plus it’s also really a gratitude check-in too. Life can seriously pass us by so fast and this section really allows me to reflect on life in real-time and be thankful for all that I have.

I hope you guys have found this helpful! I think it’s also important to note that my process has evolved a lot over the years and is a combination of a lot of things I’ve tried. So don’t be afraid to adjust it and make it your own!

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Could you use a little support with this process? I created a monthly goal planning worksheet to walk you through it step-by-step!


Monthly Goal Check-in :: Wins, Milestones and Progress from August
Anna Osgoodby Life + Biz :: Monthly Goal Check-in ::Wins, Milestones and Progress from August| Goal Planning | Goal Progress | Goals Coach

Time for some Monthly Goal Check-In action!

I set some BIG goals for myself and got ish done so I'm coming out of this month feeling pretty damn good! Here's a breakdown of some of the wins I'm most proud of:

Hit my goal of writing 12 blog posts this month

I'll be honest, this was an ambitious goal for me but frankly, I wanted to push the limits to prove to myself that I could do it, and I DID! 💪 Guys, that was more blog posts in a month than I wrote in all of 2019.😱 Giving my blog more attention this year has been a big priority of mine and it feels good to be making it happen.

Launched my Get Your Goals page on my website + my first set of worksheets!

For the last year, I've been adding ideas to a Google Doc with different course ideas, blog posts, and a whole lot of other things and this was the month I made it official! P.S. you can check it out here!

Hit Monthly Income Goal at Bold & Pop for the first time since the pandemic

We hit the monthly income goal I set for our biz for the first time since the pandemic started and I just have all the happy tears about it 😭😭😭 Real talk, this year has been really tough being a small business owner. And while it won't be a year we break records, the fact that we've survived, gotten creative, and are growing again just has me feeling every level of grateful.

Added a new Page on Bold & Pop’s website for Social Media Businesses

We added a new page on the Bold & Pop website specifically for social media biz owners. Now you can sign-up for the waitlist for our next Social Media Business Bootcamp, browse our business templates, check out the other workshops we teach, and read helpful blog posts all in one spot.

made time for rest

With all of that progress comes the need for rest too. We made the goal of each taking a min of 20 days off this year, because we realized we were hardly taking any days off. After COVID, admittedly I let this goal slide because we've been in survival mode, but this month I took time off + scheduled the rest of my days for the year.

That's a wrap for me, here's your monthly reminder to take some time to celebrate some of your own wins (big and small) too! If you need some help with your check-ins or setting yourself up for success for the next month, I also have free worksheets that can help!


Why do I do goal check-ins?

I started doing goal check-ins publically as a personal accountability challenge. Working on my goals and strategies to accomplish them have always been really important and by sharing them I felt an extra weight of commitment. Plus, I wanted a way to try and encourage others to have their own check-ins and keep working on their own goals. Helping others reach their dreams has always felt like my purpose and by being vulnerable and sharing the journey of my own I hope to inspire others as well.

Home Tour :: Townhouse Living and Dining Room
Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour

This post contains affiliate links for your convenience which means if you purchase something I recommend I may receive a commission at no additional cost to you.

Welcome to our living and dining room! Something I absolutely love about our townhouse is that it gets such great light! Add in the yellow paint that’s throughout most of our house and it always has bright and cheery vibes. Which is definitely nice during our gloomy PNW winters too! Another thing that is really awesome about the space is all of the built-in shelving! I definitely didn’t waste any time filling those puppies up.

Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour
Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour

Couch: Similar | Cowhide: Similar | Pom Pom Throw Blanket: Similar | Tray: Similar

Our living/dining area is located on the main floor (which is kind of the second floor) and something else I really liked about the townhouse is it didn’t have a huge dining area. I know that’s not a popular opinion and maybe my thoughts on this will change. For me though, having a full separate dining room is such a waste of space… We really wouldn’t use one, so I love that we have an area that is functional but doesn’t take away from the use of the room. We also have a balcony right off of the dining area which gives us another little area where we can eat or hang out.

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Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour
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When it comes to our shelves, let’s be honest, they’re mostly used for my plant babies 😂🌱. They’re certainly the stars of the room with my sun-loving plants on the shelf nearest to the window and the ones that need less direct light on the other. Definitely serving out that purpose well!

For the rest of the space, I wanted them to be both functional plus highlight things that were personal to us. We do spend a lot of time in this space after all! So you’ll find that reflected through the artwork, different family heirlooms, and some of the rocks we’ve picked up from our adventures (yes we do that) that are on display. Designing each shelf was really all about purpose, meaning and a dash of styling.

Also, I’d like to let it be known that when I designed the “Let’s Stay Home” print for Evan’s first apartment… I did not anticipate the pandemic of 2020! It definitely has a different meaning these days.

Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour

Rug: Similar | Plant Basket: Similar | Decorative Suitcases: Similar

The other end of our living room, connects to our kitchen which is super handy! It’s really nice to be able to still chat while one of us is cooking and also being able to watch the TV if something is on. Plus being able to hand things through the opening if very practical.

When it came to the TV, the big opening where the plant and suitcases are was actually where the TV was intended to be. Our house was built in 2003, back in the era where the TVs were so deep! We decided against putting it there though and went with mounting it instead. It just worked out better and made more sense for us.

Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour
Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour

Light Fixture: Home Depot | Bar Table: Amazon | Bar Cart: Target | Bar Stools: Target | Shelves: Ikea

Now onto the dining room area! Like I said, this space isn’t too big but it works out perfectly for us. We had this bar table from our old apartment and decided to stick with it here too. When it comes to the dining area, my favorite part is the new lighting fixture for sure.

The one that was there when we moved in was a lot bigger and a little dated. I mean, it worked and everything, but since we opted not to have an actual dining table it ended up just looking too big for the space. Plus, with everything being very move-in ready it was really the only thing I kind of wanted to change. Queue me starting to look for light fixtures… My goal was to find something that was smaller, was a little more industrial, and wasn’t a million dollars. It took me a hot minute to find something I was into but this one ended up being perfect + it was only $150! Which, if you’ve looked at lighting before you know that’s a steal for those types of lighting fixtures.

Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour

On top of the bar cart, is my tried and true open shelving for some of my favorite glasses. I’ve integrated this design element into pretty much all of the apartments I’ve lived in since my NYC days and it’s always one of my favorites. I also swear by these shelves from Ikea for doing this. They are SO much sturdier than others I’ve tried. Another thing you can do is spray paint the hardware so you can put a little of your own touch on the look too.

Spray paint is my friend let me tell you! Another thing I spray painted was the barstools! I had a set of two but since we put the table in the middle of the room we needed another set. Of course, after buying a house I was trying to save wherever I could and didn’t want to spend the brand new price for another set. So instead, I looked on Facebook Marketplace, got a set of 3 for a whopping $25 and then I spray painted all 4 of them black so they all matched. My original two were a bronze metal color and the new ones were white, but the spray paints didn’t match perfectly so I just went black so they’d all match.

Anna Osgoodby Life + Biz :: Home Tour :: Townhouse Living and Dining Room | Tacoma, Washington Townhouse Tour

I’m a little biased but I think it turned out pretty good! Here’s a final look from the dining area peaking out onto the balcony. This is a fun little corner too because our hummingbird feeder is right outside and then they also like to sit in the trees right outside the window! They’ve officially become my unofficial pets now. Plus that tree has been moved into many rooms and was on a mission to die but has been thriving in this corner ever since so it’s staying there for the long-term! Oh to be a plant mom!

I hope you enjoyed the tour and I’ve linked to more of the products we used + some similar options below! if there’s anything specific you’re interested in though be sure to shoot me a note!

Shop the Living and Dining Room