A Year-End Check-in: Looking at What Worked (and What Didn’t)
When December rolls around, I start thinking about doing a check up on my previous year. This annual life check-in always brings up more than I expect.
I think of it with the same kind of dread as getting a physical, not dread exactly but not really wanting to see what it reveals. The same kind of dread when I look at a bank statement after a big vacation.
But my process is so beneficial that I usually dig right in after a few moments of realizing it’s “that time.” I really don’t want my last hours to be the only time I spend looking at my life, with the regrets and if only’s.
The Three Focus Areas That Defined My 2025
- Priorities
- Processes
- Letting Go of What Wasn’t Working
A Lesson from Steve Jobs: Focus Fuels Growth
When Steve Jobs returned to Apple, the company was about 90 days from insolvency, according to Jobs. He eliminated the majority of their sprawling product lines, creating a focus on only four products – well before the iPod and iPhone and everything Apple is today.
“Deciding what not to do is as important as deciding what to do.”
Whether you are an entry-level employee, an experienced mid-life career woman, or a business owner, this applies to all of us.
When a Fun Distraction Becomes a Costly One
My 2025 would be ending much differently if I’d followed this maxim. Instead, I didn’t focus on what was my keystone goal, or even my top three. Early in the year I decided to spend more time on a niche sideline, traveling as an OBC, an onboard courier.
My real business, Winning at Work by Sharon Rose Hayward, made of online workshops, career strategy coaching, and periodic insurance agency consulting, was an after thought.
I told myself that I’d created a business that was self-sufficient and didn’t need my attention 24/7. As true as this was and is, there’s a difference between paying attention to something and getting creative, doing deep work, eliminating what isn’t performing.
What’s worse, I didn’t follow my own previous goal protocol, which was reviewing how I was doing in relation to my top 3 priorities, annual, quarterly, and monthly goals.
Don’t get me wrong. I was still working as a career strategist with women, teaching classes at the women’s shelter, and working with insurance agencies where I brought value. But the focus I brought was kind of like a mom who’s scrolling on her phone while the kids play. I wasn’t engaged.
Checking where you are in relation to your priorities and goals isn’t just for entrepreneurs or corporations. I’ve been following a monthly check in for several years now. Again, I wasn’t really engaged. I didn’t make any changes because I wasn’t doing a deeper dive.
Resistance, Distraction, and the Cost of Losing Focus
How does this happen? Distractions are subtle. If you’ve read Steven Pressfield’s The War of Art, he calls this resistance. Resistance is what we need to rise up and conquer daily to keep us on track and not looking at the spice cupboard that could use a good alphabetizing.
My OBC job was a lot of fun. I traveled the world from Rome to Munich, to South Africa and Taipei. Having a tamarind margarita in Guadalajara and walking to the Main River in Frankfurt to check out ancient Roman landmarks.
I’m ending the year at status levels of the three major airlines that give me great benefits, including up to three free checked bags. Priority boarding. My own hotline for issues.
Why wasn’t this great?
As much as it was ready cash each month, the actual payment could be more than three weeks after the job. The job could have also included a couple thousand dollars for oversize and overweight baggage, customs tax, hotels and ride share expenses.
While I was waiting for the reimbursement, I still needed money for expenses. Credit card companies charge interest even when you’re waiting for reimbursement. They’re crazy like that.
I was continually trying to catch up and make sure I was getting everything paid. Even without this payment pressure, there’s nothing in my goals that provides for this. For me, it turned into an expensive, fun distraction.
The Wake-Up Call I Didn’t Want – But Needed
OBC jobs aren’t guaranteed. Beginning in September, I went from my best months ever to nothing. No quotes. Nobody reaching out. Nothing. Being naturally optimistic, I didn’t see the writing on the wall until November, when I realized I’d let my own company tread water and there wasn’t anything else happening.
A serious wake up call. And yet, it was perfect timing. I have been talking to two agencies about projects, plus opening private 1:1 career strategy coaching spots.
Why am I sharing this?
One, because it’s never too late to refocus.
And two, 2025’s biggest value has been the lessons.
I haven’t had a serious lesson year like this since 2016, when I ended what I call the “most educational relationship” of my life.
Taking an honest look at our choices and what we will put up with is valuable. 2025 is valuable because I see now in hindsight (connecting the dots) how I became complacent to my real goals and allowed distraction of fun and money take priority.
Also, no judgment. Lessons aren’t about judgment, they are about learning and changing.
My Keystone Goal + Big 3 for 2026
I’m committed to going back to basics. What does this mean for me?
Keystone Goal
For me, my keystone goal isn’t a title or a project.
It’s having consistent monthly income that gives me steadiness — in my work and my life — and the ability to build something sustainable.
This is something I’ve written about before in my post on the Power of Aligned Career Goals. When goals are aligned, they don’t drain you — they direct you.
I want a business that supports me instead of consuming me.
This isn’t about more. It’s about enough — and building from a place of steadiness instead of survival.
When this is clear, everything else becomes easier to define.
My Big 3
These are the three areas I return to again and again. Not because I execute them perfectly, but because they tell me when I’m drifting.
Health
Mental, physical, and emotional health come first. If my mind is cluttered, my body tired, or my spirit ignored, nothing else runs smoothly. Hiking, reading, yoga, meditation, journaling, and quiet are not luxuries for me — they’re infrastructure.
Finances
My work matters. I want income that reflects that — through career coaching, Winning at Work programs, and corporate projects that allow me to contribute at a meaningful level. This isn’t about chasing money. It’s about building a business that sustains my life.
Family
Time with my kid matters more than productivity metrics. So does staying connected to my brother and sister, and protecting the few friendships that really matter. The circle is small on purpose. The life inside it is full.
Releasing What No Longer Serves Me
Release what’s not serving me. This isn’t quite as easy as it sounds. Maybe it doesn’t sound easy. Something that’s not serving me means not aligned with my keystone goal or Big 3. This isn’t simply saying no to an OBC request. Here are some things that also don’t serve me:
- Dining out more than once a week
- Having more than one drink, two maximum
- Skipping my daily activity, whether a brisk neighborhood walk or hike in the woods
- Saying yes to meetings or committees that don’t feel like a burning yes
What’s the last piece of this? Looking at wins. If I don’t look at everything that actually fell into place and worked out in 2025, I will feel a little bit like a failure. Like 2025 was a big bust.
Wins Worth Remembering
Here are a few:
- My kid and I had great trips up north to the Upper Peninsula and Traverse City, including White Fish Point where the Shipwreck Museum is – think The Wreck of the Edmund Fitzgerald. The Cherry Festival and visiting lighthouses. Chicago where we stayed downtown, finally did the riverboat architecture tour 5/5, took the el to the Garfield Park Conservatory, walked five plus miles each day and ate lots of good food.
- Our garden produced garlic, tomatoes, peppers, lettuce, and basil. We will be eating our own homegrown garlic for a few more months, and used 4 of the biggest bulbs to plant for the 2026 season.
- We’ve been cooking at home so much more, almost like 2020. Brian bakes bread a few times a week now, round Italian boules. I’ve perfected an aglio olio pasta with our homegrown garlic, lemon juice, grated parmesan, and a sprinkle of crushed red pepper flakes.
- I’ve had more opportunities to set boundaries and ask for what I want, I’m looking for a break. Seriously, for someone who has spent years thinking, “this is okay, I can make this work”, to now hearing those words in my head as a red flag, and choosing to say, “no, this is not okay.” There’s always a lesson.
- Some people are not meant to be in my life. I’ve let them go on their own way. This is a win.
2026 feels like a fresh start, like all new years for me. I don’t set New Year’s resolutions. I have my keystone goal, my Big 3, my overall annual goal, quarterly and monthly goals. Sometimes I can get a month’s worth of accomplishments in a single week, so yes, I have weekly goals. And you guessed it, daily goals.
It feels so good to be back on track. It’s important to look back and connect the dots. I don’t feel rushed to escape this year; I feel finished with it.
Final Reflection: Trusting the Dots
I’ll finish with one of my favorite quotes, another from Steve Jobs.
“You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future.”
What lessons did 2025 have for you? What are you looking forward to in 2026? And do you have a keystone goal or a Big 3?
Take a few minutes and write it down – and I’d love to hear your thoughts.
This is how I know I’m in alignment — I see the value of 2025, I’ve released the weight of judgment, and I’m stepping into 2026 prepared.
Read the book that started it all.
Winning at Work: A Practical Guide to Career Success plus the companion journal. Both available now on Amazon.
Sharon Rose Hayward is the author of Winning at Work: A Practical Guide to Career Success and founder of Winning at Work. A writer, teacher, and mentor, she helps women and organizations unlock their potential by focusing on their best work — the work that delivers the greatest value and fulfillment. Through her corporate consulting, Sharon partners with teams to strengthen confidence, clarify purpose, and translate talent into measurable results. Her insights have been featured on Good Morning America, Yahoo! Finance, Career Connectors, theSkimm, and Essence.