By Dylan Sullivan, Managing Director, Accounting & Finance
After 100+ recent conversations with hiring managers and accounting and finance professionals who are thinking about their next move (or quietly wondering if they should be), what’s stood out to me is thoughtfulness, a bit of hesitation, and a real desire to make the right decision. Many candidates are asking smart questions about timing, flexibility, growth, and long-term fit. But in many cases, that caution is tipping into something less helpful: waiting for the perfect opportunity to appear before engaging at all.
What follows aren’t rules or market predictions, just a few patterns I keep seeing repeat themselves in conversations with candidates at all levels. If you’re navigating your own career decisions right now, I hope this helps you think a little differently about momentum, optionality, and what actually matters when making a move.
Waiting for the “Perfect” Job Can Quietly Stall Your Momentum
Many candidates tell me they’re hesitant to interview unless a role checks every box. I completely understand the instinct, but when you know it’s time to consider a move, it’s important to at least take meetings.
That doesn’t mean applying indiscriminately. It does mean using interviews as a way to sharpen your story, learn what the market values, and pressure-test what actually matters to you. If a role doesn’t check every box, you can—and should—hold it to a higher standard before moving forward. But skipping the conversation entirely can limit optionality more than people realize.
One pattern I see far too often is candidates who tell me they know they’re not in the right role, but then wait, sometimes for years, for a “unicorn” job to appear. We’ll talk through what they want, what’s missing, and what might excite them next… and then nothing happens because the opportunity isn’t perfect on paper.
What’s important to remember is this: the job you think is perfect for you is also perfect for a lot of other people. Those roles don’t come around often, and when they do, they’re competitive. Waiting indefinitely for that one ideal opportunity is how many people end up feeling stuck, frustrated, or increasingly disengaged in roles they already know aren’t right.
Progress doesn’t require settling, but it does require movement.
Days in the Office and Flexibility Are Not the Same Thing
This topic comes up constantly. Many firms have moved back to four or five days in the office, and for candidates with long commutes or young families, that can feel like an immediate deal breaker.
What I’d encourage is nuance. Some five-day-a-week firms are far more flexible in practice than their policy suggests. Others offer real work-life balance, with shorter days, predictable schedules, or leadership that genuinely respects boundaries.
If a role checks nearly every box except in-office expectations, it’s often worth having the conversation rather than assuming the worst.
Another pattern I’ve seen repeat itself: candidates who make days in the office their number one deciding factor often end up disappointed later. Office policies change. Leadership changes. Business needs shift. What starts as a three-day or four-day model can quickly move in another direction.
Because of that, I’d caution against using in-office requirements as the ultimate deciding factor in your search. Flexibility is important, but it’s rarely static. Long-term satisfaction usually comes from the work itself, the people you’re working with, and the growth the role provides, not just the current policy written on paper.
Don’t Wait Until You Have to Leave to Start Interviewing
This is old advice, but it’s showing up again for a reason. Candidates who wait until they need to leave their job often feel rushed, and that’s when frustration builds and compromises happen.
If you think there’s a chance you’ll want to make a move in the next 12–18 months, start earlier. Update your résumé. Reconnect with your network. Talk to a recruiter. Maybe even take a few interviews.
Sometimes that process confirms you’re ready to leave sooner than you thought. Other times, it reinforces that staying put is the right call. Either outcome is valuable, and far less stressful than making decisions under pressure.
A Final Thought
The most successful career moves I see aren’t driven by perfect timing or perfect job descriptions. They’re driven by informed decisions, realistic expectations, and momentum.
Being selective is smart. Being thoughtful is smart. But waiting indefinitely for everything to line up exactly right often works against the very clarity candidates are seeking.
My role at Landing Point is to help candidates think through these decisions before they become urgent. When the right opportunity does come along, I want you to be ready to evaluate it with confidence rather than pressure.
If you’re starting to ask yourself whether your current role still fits, I’m always happy to talk through what you’re seeing and help you think about next steps, even if that step is simply staying put a little longer.
These patterns continue to surface in hiring decisions across the market. For an additional take on the hiring side, see more here: https://landingpoint.com/blog/what-im-hearing-in-the-market-after-100-year-end-conversations/.
About Dylan Sullivan
Dylan Sullivan is a Managing Director at Landing Point and a leader within the firm’s Accounting & Finance practice, where he oversees executive search and advisory work for asset management, private equity, and family office clients nationwide.
With more than a decade of experience in finance leadership recruiting, Dylan partners with CFOs and COOs to help them design and scale their teams. Notable searches include CFO and Controller placements for alternative investment and growth-stage financial services firms.
Before joining Landing Point, Dylan spent four years in Audit at Deloitte’s New York office, providing him with technical accounting expertise and insight into financial operations that inform his consultative approach today. He earned both his bachelor’s and master’s degrees in accounting from Villanova University. Dylan lives in Florida with his wife and two daughters and is a dedicated sports fan who enjoys basketball and travel.