Anna Treesara - Career Coach

“I thought I’d feel further along by now.”

It’s something I’ve heard from multiple clients recently, and honestly…also from myself.

Career transitions are rarely as straightforward as we imagine.

Over the past few months, while stepping into a new role and continuing my own recovery from burnout, I’ve been reflecting a lot on what forward momentum actually looks like.

Those thoughts inspired the relaunch of my newsletter, now called Branching Forward.

I didn’t write much last year while navigating my own transitions, but this relaunch expands the focus beyond transitioning teachers to anyone navigating a career pivot, professional challenge, or period of recalibration.

In this month’s edition, I explore the part of career transitions most people underestimate and introduce a simple framework I often see play out in these moments: the three phases of sustainable momentum.

If you’re in the middle of a shift and feeling like you should be further along, this reflection might resonate.

You can read the full newsletter here: https://mailchi.mp/6595a41b5a91/march-2026

And if you’d like future editions delivered to your inbox, you can subscribe here as well: http://eepurl.com/hRv7P9

Lately, I’ve been thinking a lot about pace.

This past weekend, my toddler got sick, and he very much so just needed a rest day and extra snuggles.

It forced me to let go of things like wake windows and caloric intake, and just let him rest.

It also made me wonder why, as adults, we try to push through when we clearly need rest.

I’m used to moving at 100 miles per hour. Even when I’m sick, I power forward. I’ve done the same thing in every job hunt — scouring job boards for hours, sending out a flood of applications, stacking networking calls back-to-back.

Ironically, I coach my clients to do the opposite.

I’ve literally written about this in my workbook and built rest into my clients’ transition plans. I help them create sustainable, manageable job search strategies.

And yet, taking my own advice? Still clearly working on it.

Transitions don’t require constant acceleration. They require intention.

Your pace changes based on what’s happening in your life. I have to remind myself that’s not weakness; it’s wisdom.

Whether you’re leaving the classroom, pivoting industries, pursuing a promotion, or simply figuring out what’s next, you don’t have to sprint the entire way.

The goal isn’t just to land the next role. It’s to arrive there whole: fully prepared and ready to take in all the magic of the accomplishment itself.

If you’re in the middle of a transition and want a strategy that’s sustainable (not burnout-inducing), I’d love to support you.

You can book a clarity call with me here:
www.tutoringtree.org/careercoaching

Let’s build your next chapter at a pace that actually works for you.

Happy Lunar New Year 🧧 2026 is the Year of the Fire Horse, which is often associated with high energy and forward momentum.

If I’m being honest, I haven’t exactly felt “high energy” lately. I’m still very much in a season of transition and recovery from burnout. However, this new year has been a gentle reminder that momentum doesn’t always have to look like speed. Sometimes it looks like rebuilding strength, finding rhythm, and moving forward with more intention.

As a recovering perfectionist, I caught myself thinking that I needed to somehow ace this most recent transition before I could show up fully as a career coach again. Instead, what I’m realizing is that being in the thick of it — navigating uncertainty, recalibration, and empathy in real time — actually deepens my ability to support others.

To my , if you are also feeling low energy and overwhelmed by the multitude of potential career paths beyond the classroom, know that I’m here for you!

Also, it’s not a race; you have to find the pace that works best for YOU. Book time to chat with me below ⤵️

www.tutoringtree.org/careercoaching

Here’s to welcoming the Year of the Fire Horse in a way that honors where we actually are, not where we think we should be 🐎✨

It’s been a while since I’ve shared more in-depth or content. To be honest, I’ve been deep in the transition trenches myself.

As a mom, watching my 1-year-old son navigate transitions of his own has been a quiet but powerful reminder of how hard change can be, no matter how old you are. New routines, disrupted sleep, developmental milestones — even when the change is positive, it still requires a lot from the body. Seeing how much effort it takes for him to adjust has softened the way I think about transitions in my own life.

I’m about a month into my new full-time job, and last week also marked the 8-year anniversary of when I left the classroom. I had forgotten how much that date still impacts me. Our brains tend to push us to move on, but our bodies somehow always remember, and I think mine was craving a bit more self-care.

This past year was filled with transition: returning from maternity leave, navigating working mom life while running my own business, and making the difficult decision to step away from full-time work so I could slow down and reflect on what this next professional chapter should look like as a working parent.

Now, I’ve landed in a role outside of education for the first time, one that still allows me to leverage many of the skills I’ve developed over the years.

What I underestimated though was just how difficult this transition would still feel.

Transitions don’t end when you land the role. They’re entire chapters, each with their own pace, lessons, and moments of adjustment. Instead of rushing through this one, I’m learning to let myself experience it fully.

If you’re a figuring out what life beyond the classroom could look like, I’ll be sharing more reflections and guidance soon. I also offer FREE initial consultations if you’d like support along the way 🫶

🔗 www.tutoringtree.org/careercoaching

Two weeks ago, I made the tough decision to step away from my full-time job to focus on my son, Liam, and reflect on what’s next professionally. Transitioning from any full-time role, whether in the classroom or beyond, isn’t easy.

Here’s what I’ve learned so far:

🏃🏻‍♀️ The pace hasn’t slowed down:
Even though I’ve stepped back from full-time work, I’m still juggling my tutoring and career coaching business, and as Liam’s 1st birthday approached, life’s been busy! For those transitioning out of teaching, I know how challenging it can be to balance everything.

🎁 Being present is a gift:
Spending more time with Liam has reminded me how important it is to savor the moments that truly matter. Transitioning can get overwhelming, but being present with yourself and your loved ones is something we often neglect.

💆🏻‍♀️ Prioritizing myself is non-negotiable:
I carved out some much-needed “me-time” to celebrate surviving my first year of motherhood: haircut, solo sushi date, massage, and a new plant. It’s a reminder of the importance of self-care, especially during a career transition!

😩 Burnout is real:
Balancing full-time work, motherhood, and my business was draining. This break has allowed me the space to recalibrate. Many of you transitioning out of teaching may feel the same way. It’s important to listen to what your body and mind need.

🤝 The power of community & networking is undeniable:
Since announcing my transition, I’ve been supported by both personal and professional networks. It’s a reminder of how powerful community and networking are, something I always emphasize with my coaching clients. You never know when a connection might make all the difference!

As I continue to find balance (especially as a ), I’ve realized it’s always shifting. That said, I’m not someone who can sit still for long!

, I know how daunting a career shift can be. If you need support in navigating your next steps, I have space to take on new coaching clients.

Interested? Let’s chat! ⤵️
www.tutoringtree.org/careercoaching

🤰🏻👩🏻‍🍼

I’ve been a little MIA lately in the community! While I returned from in January, I STILL feel like I’m adjusting 6 months later and haven’t quite figured out what life as a looks like. Some days are great, and some days are TOUGH…like REALLY, REALLY TOUGH. On top of that, I’m also trying to keep my going too 😅

At the end of the day though, I’m still extremely grateful for where I’m at professionally, and I constantly reflect on how different my life would be had I still been in the classroom. While things are tough some days, I think I’d still choose my current career over teaching. I’ve been so fortunate to have the flexibility to , adjust my days as needed for pediatrician appointments, early daycare pickups, etc. With the limited mental and emotional capacity I have nowadays, I’m so glad I can spend that trying to be very present with my son during the evenings and weekends. I just don’t think I would have personally been able to figure that out as a teacher and a parent.

If you’re a and are ready to take the next steps in your career journey, let’s chat ⤵️

www.tutoringtree.org/careercoaching

Jumped on this trend, but late to post because 😅

Also, I found myself getting sooooo perfectionist about this trend and not loving certain details about it. Then, I realized that I need to start leaning back into what is — the constant enemy for someone who is a 🫶

Aside from this, I actually had tons of fun playing around with . Something I always advise to do is to play around with various and if possible even the produced by the companies they’re interested in working for! It’s a great way to stay in the learner’s mindset as well as upskill overall 🤓 Educators can then list these skills on their resumes 👏

What are some other tech tools transitioning teachers have explored?! What AI tools have been really fun to play with?!

it has been a while since I sent out a newsletter…since April of last year actually 😅 those who already follow me closely know that I was sort of busy growing a human and becoming a 👩🏻‍🍼

But I’m back to it now, and you can check out my latest newsletter here: https://mailchi.mp/58c1e95f42c3/january-2025

Lots of reflections around the challenges in this transition to motherhood, rediscovering my identity, and finding my support networks — very similar to my experience when I transitioned out of the classroom back in February 2018!

Ready to take those next steps and figure out what’s next in your career?! Let’s chat ⤵️

www.tutoringtree.org/careercoaching

I pushed myself out of my comfort zone yesterday and attended my first dinner, where I was able to be in such great community with fellow moms.

Honestly, I almost didn’t go. This was my second week back at work, and I was mentally and physically exhausted. I was feeling immense before even stepping foot out the door. Leaving would mean that I didn’t get to rest and decompress from the work day, that I’d leave my husband behind to take care of our baby solo, that I would miss out on my baby’s bedtime.

I mustered all the energy I could, and with the wonderful support from my husband, I peeled myself off the couch and walked 15 minutes in the brutal Chicago cold to attend this dinner.

And I’m SO GLAD I attended. Of course, anything like this is always initially very awkward. You look around the room, waiting to see who will make eye contact with you, you smile, and slowly make your way over. After a few seconds (that actually feel like a century), you begin chit chatting. Before I knew it, I was connecting with others and sharing vulnerably about my and challenges.

I walked away with a few additional phone numbers and feeling so rejuvenated and validated. Many moms I talked to had older kids, and when I mentioned that I have an almost 4-month old and have just returned back to work, everyone IMMEDIATELY asked how I was doing REALLY, and if I was okay.

You can’t get that kind of support from just anywhere. I’m grateful I stumbled upon this group, and I’ll definitely be taking advantage of future events.

As I continue to explore my new identity as a mom, I’m again reminded of how difficult transitions can be and think back to my transition out of the classroom back in February 2018. What got me through that challenging time was finding support networks and figuring out who my cheerleaders were.

please allow me to be your cheerleader and help you figure out the next steps in your ⤵️

www.tutoringtree.org/careercoaching

And that’s a wrap on my first week back at work after ! While I was very ready to go back to work and use my brain for something other than feedings and diapers, it was still more challenging than I had anticipated. Though I have the privilege of , it was still tough knowing that my baby was right down the hallway, and I had to work extra hard to stay focused during live calls and other priorities I had for the day.

All that being said, I’m so grateful to work at a company that offers and flexibility. I’m also grateful to have amazing familial support helping out with childcare. Finally, I’m grateful that I transitioned out of the classroom when I did. I don’t think I could have handled having to go back to the classroom after having my first baby.

As I transition into my Director of Operations role, it makes me think deeply about what a world looks like where the STANDARD is to make the workplace as inclusive as possible for working parents, especially working moms, and to take it a step further, working moms of color.

Big thank you and shoutout to the wonderful team at Leanlab Education giving me such a warm welcome back and making me feel so valued! Looking forward to getting back to the important, mission-driven work we do!

as a reminder, I’m also open again for FREE initial coaching calls. Let me help you land a role at a company that has these amazing benefits and flexibility! Schedule a call with me at www.tutoringtree.org/careercoaching 📆

Definitely leaning into my 👩🏻‍🍼

I became a first-time mom to this small human back in late September, and this transition has been incredibly transformative. I’m so grateful for how it’s allowed me the opportunity to be reflective and consider how this can make me an even better to .

I’m reminded of when I transitioned out of the classroom back in February 2018 and the many challenges that came with it. I’m reminded of how I had to rediscover myself because being a teacher was all I ever knew my identity to be.

As I navigate this new transition of motherhood, there are several familiar and similar emotions. How do I stay true to myself while also learning how to incorporate this new identity of “mom”? What has happened to the person I was before I became a mom? What pieces still exist from before, and how do they fit in with my new identity?

All in all, transitions are TOUGH. That’s why I wrote a workbook for teachers who are considering transitioning out of the classroom. You can check it out at www.tutoringtree.org/workbook!

I created this workbook because I know that one-on-one coaching may not always be a viable option for teachers, and I believe in making opportunities accessible for people no matter the circumstances.

As we get further into December and closer to winter break, it truly is the perfect time to take some additional time to reflect and consider what next steps can potentially look like.

Are you ready to envision a life beyond the classroom walls? Purchase my workbook or book a free call with me to get started on this new journey ⤵️

www.tutoringtree.org/careercoaching

Happy December, !

I’m so excited to share that I’m slowly coming back online from , and I’ve opened my Calendly back up for FREE 15-minute initial consultations 📆 you can book time with me at www.tutoringtree.org/careercoaching!

Are you thinking about transitioning out the classroom? Unsure where to start? What options even exist for you? Or maybe you’ve already started the process and have run into some roadblocks?

Wherever you are in your journey, I can help! 🙋🏻‍♀️

If you don’t already know me or just need a quick refresher ⤵️

I’m a former high school English teacher who taught for a year in Thailand and then 3 years in Chicago.

I thought I’d be a teacher forever until I realized it just wasn’t sustainable for me and my mental health.

I transitioned out of the classroom in February 2018 and since then have started my own tutoring company as well as worked in education nonprofits and edtech.

In January 2022, after having hired several teachers to join my Customer Success team at a series A edtech company, I realized I really enjoyed coaching former teachers and helping them transition out of the classroom.

I’ve coached dozens of teachers, helping them successfully land fulfilling and impactful roles through customized one-on-one coaching, resume workshopping, LinkedIn optimization, and interview preparation.

I briefly closed my Calendly back in September because I recently became a first-time mom to a small human! This transition has been incredibly challenging, but just like when I transitioned out of teaching, I’ve used my resources and have leaned on my wonderful support networks to navigate these choppy, unexpected waters.

Ready to do the same and figure out what your options are beyond the classroom? Let’s chat! ⤵️

Book a call with me at www.tutoringtree.org/careercoaching 📞