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Monthly Goal Check-in :: Wins, Milestones and Progress from October
Anna Osgoodby Life + Biz :: Monthly Goal Check-in :: Wins, Milestones and Progress from October

October was definitely a wildddd ride over here. I’ve found myself smack dab in the middle of a season of change and while I’ve been trying to keep up with everything I’ve debated if I wanted to pause my updates for a bit. Let’s be real, I’ve thought about that quite a few times this year because… 2020!

I keep on showing up though because each month I remember that life is NEVER linear. Whether we’re living through the shitstorm that is this year or it’s another, we are ALWAYS going through ups and downs. That’s life for you! And if you wait to do things until life has calmed down… or only acknowledge your progress during the good times then you’re going to miss out on a hell of a lot.

Every month we have a new opportunity for growth and I love doing my check-ins because they remind me of just how much can happen in a month and help me realign for the next. Even more important, especially during this chapter, they remind me of just how strong and truly capable I am to accomplish big things even when life is a little cray cray!

So let’s get down to my highlights (both big and small) this month!

  1. I hit 80% of my yearly website traffic goal for my blog and had my top month of the year! That, even despite coming in short on my goal for new posts this month.

  2. Signed project contracts worth 20% of our annual business this year in one week’s time 😳 You could say it’s been a busy month for new business

  3. Invested in a course to learn a new skill I’ve been wanting to learn for awhile

  4. Started (and actually stuck) to a new skincare routine. Yes, quite the contrast to the others but… self-care

  5. Set limits on social media during my off hours and have cut back on my daily usage which was so necessary this month

I hope this update will encourage you to take a few minutes to reflect on your month as well! As always, if you want a little help through the process too, I have free downloads at the Get Your Goals section of my blog too! 🙌


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.

Monthly Goal Check-in :: Wins, Milestones and Progress from September
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I’ll be honest, this month was a challenge. One of those where you just feel like it’s one thing after another. The good, the bad, and the emotionally draining.

I’ve been hammering this message in a lot during the pandemic but this month I needed it for myself too… The reminder that even when things are tough, there is still plenty of good.

When we’re overwhelmed it can be easy to fall into a negative fog and only focus on what has gone wrong or things that are stressing us out. The quote, “you find what you’re looking for” really rings true here.

Despite the challenges this year has brought all of us though, I want to encourage you to also make time to acknowledge some of the good. For me, I do this during my monthly check-ins where I not only reflect on my goals but also life in general. It’s a time to pause. A time to reflect. A time to realign and refocus.

Admittedly, this month I fell short on quite a few things I set out to do. Life happens and there were things I needed to hit the pause button on so I could reprioritize. Truthfully, I was even dreading doing this month’s check-in. When I did though, I realized that even with all of the curveballs I still had quite a few wins. Wins that had I not actually taken the time to reflect on probably would have just fallen through the cracks.

This month I...

  1. Celebrated my 10 year blogging anniversary — Ten freaking years guys!

  2. Hosted our 3rd session of our Social Media Business Bootcamp at @BoldandPop

  3. Completely booked up design projects for September and was able to sign projects for October and November

  4. Hosted my first virtual meetup with @TacomaBossLadies to chat about Q4 goal planning

Mapped out my personal focuses for Q4 and Q1 and put together a launch calendar

So whether you came out of last month feeling like you crushed it or you were totally on the struggle bus, I encourage you to take a few mins to check-in. You likely deserve more credit than you’re giving yourself. We’re often our own toughest critics and acknowledging those wins (even when they’re small) can be instrumental in pushing us forward.💗


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.

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!