Your Mid-Year Check-In: Questions Every Ambitious Woman Should Ask
Life moves fast when you’re juggling work, family, passion projects, and trying to remember if you drank water today. The days blur into each other, and somewhere between running to school or summer camp and client calls, we carry this quiet pressure to do it all and do it perfectly. Every year, I set these lofty goals in January, and inevitably, around June, I start to feel defeated, unaccomplished, and lacking in everything from inspiration to motivation. Suddenly, you find yourself saying, “Wait—how is it June already?!”
Running a business while raising two little humans has taught me something valuable: not everything we set out to do goes to plan, and that’s okay. Life rarely unfolds in straight lines. That’s exactly why we set goals and take time to check in. Not to chase perfection, but to give ourselves a little structure, a little grace, and a way to make life feel just a bit more manageable.
Sometimes, the most powerful thing you can do is pause, take a breath, reflect, and really see just how far you’ve come this year. You’ve done more than you give yourself credit for. So, if you're ready to reset, realign, or simply reconnect, here is my go-to advice for your mid-year check-in.
Can I Revisit My Goals?
Remember those goals you set back in January, the ones that are still sitting half-finished (or untouched)? Let’s take a deep breath together: it’s okay. Life shifts, priorities evolve, and you are allowed to pivot. If that goal no longer fits where you’re at or where your business is headed, give yourself full permission to rework it.
A goal that feels aligned now is far more powerful than one you’re dragging out of obligation.
However, if you have lost momentum or are just plain procrastinating, it’s time to set some small achievable steps towards reaching your goals by the end of the year.
Expert Procrastinator Tip: Yes, I am an expert at procrastination. Here’s what I suggest: Look at what you can accomplish this month. Something small. Maybe it’s just making a phone call or setting a meeting. Then look at what you want to have done in six months. Can you take a baby step towards that – a half-step, or work in progress? In addition to your “small achievable step?”
Am I Using My Time to the Best of My Ability?
Take a gentle look back over the last six months, whether that’s flipping through your calendar, scrolling your camera roll, or skimming old journal entries. Notice what actually worked for you. Was it finally hiring someone to take a few pressures off your plate? Was it the peace that came with starting your workday at 10am instead of 7am? This isn’t about judging what didn’t work; it’s about honoring what did and letting that guide your next steps forward.
Here are a few simple steps to help you reflect and realign:
Do a Time Audit: Pick one "typical" week and jot down how you actually spent your time each day. You might be surprised where your energy really goes.
Highlight Your Wins: Make a short list of three habits, changes, or choices that made your life smoother or more fulfilling recently.
Name the Drains: Without spiraling into guilt, note any patterns, people, or obligations that consistently left you feeling depleted.
Choose One Shift: Pick one small tweak for the next month—a boundary, a routine change, or a permission slip—that feels doable and nourishing.
Revisit Often: Set a reminder in your calendar to revisit this reflection quarterly. You’re evolving—your calendar should too.
Where Am I Growing—and Where Could I Use a Nudge?
Sometimes, the most grounding insights come from the people around us. If you work within a team, take a moment to ask them what they feel has worked well so far—and what hasn’t. If you’re a solo act, reach out to someone you trust: a partner, a friend, a mentor.
Side note: this matters just as much in your personal life. Ask your trusted circle what they’ve noticed from the outside looking in. We’re often too close to our own lives to see what’s actually shifting—or what’s stuck on repeat.
Here are a few ways to make the most of this kind of feedback:
Be Specific in Your Ask: Instead of “Do you have any feedback for me?”, try “What’s one thing I’ve done well this season?” or “Is there a pattern you’ve noticed I might not be seeing?”
Choose Your People Wisely: Ask folks who know your heart and your work. The goal is insight, not insecurity.
Write It Down: Document what resonates, whether it’s affirming or constructive. Reflection hits differently when it’s on paper.
Spot the Themes: If multiple people say you seem overwhelmed or you’ve stepped into your power—pay attention. That’s your breadcrumb trail.
Act on One Thing: Don’t try to overhaul everything. Let one piece of meaningful feedback shape a gentle shift.
Let that feedback guide you—not as criticism, but as clarity—to help you adjust your course for the months ahead. Growth isn’t always loud. Sometimes, it starts with a quiet conversation and a nudge in the right direction.
Have You Taken a Moment to High-Five Yourself?
While it’s essential to notice what might be holding you back at this mid-year checkpoint, don’t forget to celebrate what’s actually working. That better balance between meetings and school pickup? A smoother relationship with your boss (finally)? These wins count—and they deserve your attention just as much as your to-do list.
Life’s too short not to toast the tiny victories that usually go unnoticed. If you’ve hit a goal—or even just inched toward one—pause and ask yourself: What helped make that possible? Then, take that momentum and carry it forward.
Here are a few simple steps to make your wins stick:
Make a List of 3–5 Wins: Big or small. From launching a new project to just surviving May (aka parenting’s Olympic Games).
Identify What Worked: Was it better boundaries? More sleep? Asking for help? Write it down so you can repeat it.
Create a “Win Ritual”: Light a candle, play your hype song, text your best friend—whatever makes it feel real.
Share One Win Publicly: Tell a colleague, post it in your stories, or jot it in your journal. Celebrating aloud reinforces your progress.
Apply the Magic Elsewhere: If something helped you succeed in one area, ask: Where else could I use that same energy or support?
Celebration isn’t fluff—it’s fuel. Let it remind you just how far you’ve come and what you’re capable of next.
What Are the Numbers Trying to Tell Me—at Work and at Home?
If you're someone who finds clarity in data, don't limit that insight to your business. Whether it's sales, engagement, client bookings—or screen time, sleep hours, or grocery bills—your numbers tell a powerful story. They're not about judgment; they’re about direction.
I’m a big believer that data can cut through the emotional noise and help you see what’s actually working—where momentum is building, where energy is draining, and where you may want to shift your focus next.
Here’s how to let your numbers speak, both professionally and personally:
Pick 2–3 Key Metrics That Matter Right Now:
For work: Email open rates, revenue growth, new inquiries.
For life: Step count, time spent on social media, money spent on takeout, hours of sleep.
Track & Compare Trends:
Are you more productive when you wake up later?
Does your mood improve on weeks you work out more or spend less time scrolling?
Notice What’s Up—and What’s Not:
If something’s thriving (your client referrals, your energy levels after Sunday meal prep), take note.
If something’s consistently low (engagement, personal time, connection with your partner), that’s a flag—not a failure.
Run a Mini Life Experiment:
Adjust one thing—like reducing phone use after 8pm or batch-working your emails—and see what shifts over two weeks.
Let the Data Drive One Tiny Change:
Make one adjustment based on what you learn—no overhaul needed. Small, informed tweaks lead to big impact.
You don’t have to track everything to feel empowered—just enough to see the patterns that matter. Whether it’s your business or your bandwidth, the numbers don’t lie. They just need you to listen.
What Should I Actually Do with My Mid-Year Check-In Results?
So, you’ve asked the big questions and gotten honest answers. Now what? It’s simple—but not always easy: use what you’ve learned to show up better for yourself. Let your insights become action. Identify what’s working, acknowledge what’s not, and let the feedback you’ve gathered (from others and from within) be your compass for the next six months.
That might mean tweaking your goals, ditching outdated routines, trying a new strategy—or finally giving yourself permission to build a life that fits you now, not the version of you from two years ago.
Here’s how to put your reflections into motion:
Pick 1–2 Themes to Focus On: You don’t need a complete overhaul—just a clear direction. Choose the areas where a shift would make the biggest impact.
Set a Mid-Year Intention (Not a Resolution): What do you want to feel more of? Peace? Purpose? Progress? Anchor your action in that.
Create a Light Accountability Loop: Find a friend, mentor, or coach to check in with monthly. Or set a calendar reminder to reflect on what’s working.
Plan a Reset Ritual: Whether it’s a weekend offline, a solo planning session, or a brain-dump journaling day—carve out intentional space to start fresh.
Need Help Turning Insight Into Impact?
Maybe you’re sitting with your mid-year clarity—but don’t know what to do with it. You’ve got a brand, a voice, or a story in your heart… but you're unsure how to shape it, share it, or sell it. That’s exactly where the Womanhood Unwrapped Branding Course comes in.
This self-paced course walks you through:
✅ Clarifying your voice and message
✅ Defining what you really want your brand to stand for
✅ Building a brand on a budget that reflects your values, vision, and real life
✅ Creating a plan you can actually stick to
Whether you’re a solopreneur, creative, or just finally ready to put your work out into the world—this course gives you the clarity and tools to move forward with confidence.
You’ve done the reflection. Now let’s build the brand that matches the woman you’re becoming.
