How to *Really* Know When You’re Ready for Your Next Move
An in depth Q&A with Cydnee DeToy, an executive coach for ambitious millennial women.
Welcome back to Reframed! Work is complex, career advice shouldn’t be.
I’m Ashley Rudolph and I write this newsletter for people who are ready for the next level in their careers. Reframed readers describe the experience best: “There’s a depth here that I lack in many a Fast Co click bait article. You push beyond the superficial answers.”
Sometimes the hardest part isn’t leaving your job. It’s finding the clarity to know whether your decision is the right one.
There have been a few times in my career where I was stuck in the liminal space of a messy transition.
You know that in-between state where you know something needs to change, but the right move isn’t obvious yet? Those moments feel almost impossible to navigate because you’re not just making a career decision; you’re making a personal one. Your mind fills with questions like:
Am I growing here or am I stagnating?
Do I stay somewhere I feel overlooked or go somewhere I might feel valued?
Will this move unlock more opportunity? More flexibility? More money?
….Or will it cost me something I won’t get back?
A few years ago, I left a job for what felt like the perfect next step, until ultimately it wasn’t. And years later, I still wonder whether a direct, honest conversation with my manager could have gotten me where I wanted to go without starting over in a new role.
That’s the tricky thing about transitions: when it’s right, you feel grounded, supported, and genuinely excited about what comes next. When it’s not, you’re so focused on your escape that you can’t think about what’s next.
That’s exactly why I’m excited for to share her expertise in today’s guest feature.
Cydnee is an executive coach and author of the Ambitious Millennial Woman newsletter. Her focus is helping women through major career pivots and personal breakthroughs — exactly who I’d want to talk to if I were feeling stuck. I’ve seen Cydnee write about her experience leaving an org too early and I knew I needed to bring that conversation here. She has a grounded, clear-eyed way of sharing her own learnings, and through her work as an executive coach, she helps people decide whether they’re ready to take a leap.
Let’s dive in!
DEEP DIVE
To Stay or To Go: The Ultimate Q&A with Cydnee DeToy
1. Has there been a time when you left a role before you should have? What was happening for you at the time, and looking back now, what might you have done differently?
Ha! I didn’t just leave too quickly – I sprinted away and blew up massive learning, earning and networking opportunities along the way. In 2017, I was two years into my first impressive, career-building consulting role. I was getting everything I wanted - promoted early, leading a team, owning client relationships, good brand, great compensation. And, I was deeply utterly exhausted. The hours were bruising. The client relationships tense. The team under-resourced.
I was so burnt out and desperate for a change that I pounced on the first opportunity that landed in my inbox. I took a lateral move at a boutique consulting firm, assuming it had to have better work-life balance, right?!
Woof, I was wrong…very wrong. While I wasn’t on a plane every week, I was working 9-9-6 for the first time in my life. It took years of candid conversations with my leadership team, introspection and advocating for myself to reshape that role into something that worked for me.
When you want to leave, I know it feels urgent. However, pace yourself. Giving yourself a little time to breathe, reflect and plan now will prevent you from having to make another move in 12 - 18 months.
2. What’s your framework for deciding whether to move on or wait it out? If someone feels stuck or restless, what steps would you recommend to help them pause before making a big decision?
When you feel over it, it’s likely hard to have the critical thinking, creativity and emotional capacity to make a big decision about whether to leave or stay. While it might not feel as immediately satisfying (quitting can feel so good!), spend a little more time refueling now to ensure that you make the right decision long-term.
Give yourself space to think and feel. This may feel impossible given the pace of your work (and life!), but I’d argue that it’s a non-negotiable before you leave. Make sure you carve out meaningful time to really check in with yourself before you decide what to do next.
Give yourself a timeline with regular milestones. If you want to try to improve your current situation before leaving, make it time bound so it feels feasible but not indefinite.
Focus on your personal life. Often the reason work feels so fraught is that it is all-consuming. It makes the highs and lows of your job feel like a roller coaster you can’t get off. So have fun, spend time with loved ones, do something new or creative. The more you amp up your personal life, the more it will put the work drama in perspective.
IN CASE YOU MISSED IT →
If you want to deep dive on this a bit more, I shared some tactical advice for knowing when it’s time to quit with the NY Post and wrote about it on Reframed. Cydnee and I share similar POVs on this topic.
3. What are some of the most common struggles that feel like signs to leave but are actually indicators of growth or a hard season that could pay off on the other side?
Great question! And, the perfect reminder that there’s good, healthy discomfort and messy, misaligned discomfort. Here are a few good discomforts you should embrace:
Ramping up after a promotion or in a new role: The first three to six months in any new role are meant to be messy, chaotic and imperfect. You may want to opt out immediately but remember – you’re learning a new language and one day you’ll be fluent. If it wasn’t uncomfortable, something is probably wrong!
Shifting from doer to leader: This one is going to feel edgy and perhaps like you’re doing everything wrong. You may feel overwhelmed and want to contract to something safer, but keep going and trust that you’ll find your voice and rhythm with time.
Building political capital: Another form of discomfort that gets misread as a sign to leave is the slow, awkward process of building political capital. Often, this period is the necessary groundwork for future influence. Once you’ve established trust, shown consistency, and delivered a few early wins, your job becomes significantly easier and your impact grows exponentially.
4. I was listening to Ego Nwodim’s interview on the Death, Sex & Money podcast recently, and she said something about her departure from SNL that stayed with me: “it takes courage to leave the party at the right time” and “sometimes you stay longer than you should because you’re afraid of the unknown”. How do you think about that tension between the fear of leaving too early versus staying too long and letting things drag out?
Ooo, I love this one. First things first, let’s take the pressure off that you’ll ever be able to perfectly nail the timing of your departure.
What I’ve found in working with my clients is that the real risk is that you’ll overstay your welcome. We - ambitious, high-achieving professionals! - are wired to be thoughtful and plan extensively for big transitions. However, know that planning for too long and overstaying might make you so exhausted you need to take a break before your next move. Or, you’ll be so frustrated that you burn bridges as you leave.
INSIGHTS
Make sure you give yourself space to reflect, ask yourself the real, hard questions and trust your intuition that you’ll know when it’s the right time to leave. You’ll be able to make whatever is next work.
- CYDNEE DETOY
TAKE ACTION: CYDNEE’S FRAMEWORK
How to Decide Whether to Stay or Go
If you’re in that space where the next step feels fuzzy, here’s Cydnee’s advice on what to do before you make a move.
Talk to your boss and let them in on what you’re feeling, so you can look for solutions together. It’s expensive to replace good talent. Your boss is incentivized to find a way to keep you at your company. I’m a firm believer that when you do make the final decision to leave a company, your boss should never be surprised.
Explore every opportunity to make it work internally, to make the most of your career capital. You’ve invested years of hard work at your current company - now is the moment to capitalize on it! See if you can rotate to a different project, move internally or take a sabbatical. All of those options will buy you more time to make your next move intentionally.
Make sure you know what you’re leaving to do and why. There’s a reason people say, “make sure you’re leaving for a pull, not a push.” Your next move is going to be more successful if you feel truly drawn towards it, not desperate for an escape hatch.
CLOSING THOUGHTS
Exploring a transition with intention helps you pinpoint what you actually want next. The questions in this post won’t make the decision for you, but they will make the decision clearer. And that makes taking time to reflect worth every minute.
Thank you
for your incredible insights and see you all on Thursday :)Ashley
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 | A guest post by
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Loved this opportunity reflect and share everything I learned and would do differently -- so others can learn from my missteps. Curious to hear how this resonates.