Imagine you’ve worked for the same organisation for 10+ years and you’re about to leave.

Now imagine you’re standing outside on your last day with a suitcase. What’s coming with you, and what’s not?

I’ve been thinking about this question a lot recently due to different flavours of it coming up in coaching and mentoring conversations.

One person has spent many years with the same employer and is struggling to work out how transferable her success really is when so much of what makes her effective feels tied to what and who she knows there. Another is considering whether to leave a prestigious brand she loves being associated with. Someone else’s organisation has changed significantly around her, leaving her questioning whether she still identifies with what it’s becoming.

There can be a lot that’s positive about feeling a strong connection to where you work. It can bring a sense of belonging and shared purpose, great relationships, opportunities you’re proud of and a professional identity that feels good to be associated with.

The questions tend to become more important when something changes. Perhaps you want something different from your career, the opportunities for growth aren’t there anymore, or the company itself has changed direction, culture or ownership. Sometimes the change isn’t one you’ve chosen at all.

That’s often when it can become surprisingly difficult to work out where the organisation ends and you begin.

How much of your success is part of the furniture?

For the person I mentioned earlier, years of organisational knowledge, strong internal relationships and an established reputation all contribute to how effective she is today.

However, I suspect she’s giving the organisation rather more credit for her success than it deserves.

If you’ve spent years progressing through different roles, being promoted, taking on greater responsibility and building the relationships that have helped you succeed, there must be plenty about you that has made those things possible.

The skills you’ve developed are yours, along with the strengths and behaviours you’ve drawn on repeatedly, the judgement you’ve built through experience and everything you’ve learned when things haven’t gone to plan.

The individual relationships you’ve built may change when you leave, but your ability to build trusted relationships and develop a network doesn’t disappear when your security pass does, though.

There’s a question I often use when someone is struggling to recognise what they bring.

What must have been true about you for you to have been successful there for all those years?

The answer is usually much bigger than knowing how your current organisation works. If you’re finding it difficult to separate what you bring from what belongs to the organisation around you, Owning Your Strengths: Articulating Your Distinctive Value might be useful.

Some things really do stay behind

Of course, some of what makes you effective or gives you credibility really is tied to where you work.

I felt this myself when I left corporate life after more than 20 years. There was an immediate credibility that came with being able to say I was an MD, COO or global executive in a large technology business, particularly when I described Avanade as a joint venture between Accenture and Microsoft.

Without that shorthand, I sometimes felt smaller and less interesting somehow.

Leaving can also mean having to work out what you’re actually good at and what you want next, particularly if you’ve spent a long time within a system that has played a sizeable part in answering those questions for you, through the next role, the next promotion or simply what the business needed from you.

Then there are the colleagues and the sense of shared purpose. Some of those relationships will continue outside the organisation, others may not, and it can be hard to know beforehand which will be which.

There may also be things you’re very ready to leave behind. Organisational politics, assumptions people have built up about you, colleagues you enjoyed working with rather less, or feeling undervalued or frustrated by a lack of opportunity may well all form part of the reason you’re contemplating a move in the first place.

A move can also give you a chance to leave some of that history where it belongs.

What else are you bringing with you?

Some of the organisational knowledge and context you’ve built up over the years inevitably stays behind, but arriving somewhere new allows you to bring a different kind of value.

You’ve seen how another organisation tackled similar problems and learned from what worked there and what didn’t. Your network reaches into different places, and being new means you notice things that may no longer register with people who have been there for years. You don’t yet have all the organisational history shaping what you assume will or won’t work.

For a while at least, you’re free of the “here we go again” response that can understandably come from having lived through several previous versions of the same initiative.

You might decide you don’t want to pack your case after all

None of this assumes that leaving is the right answer.

A former client once described her goal for coaching as wanting enough clarity that, if she stayed where she was, she knew she was doing so for good reason. If she decided to look elsewhere, she wanted to be clearer about what she was looking for.

You may realise that what you want from your working life means a move elsewhere. You may also look properly at what you already have and realise how much you value it and that perhaps there is less to fix than you first thought. Sometimes the question isn’t only whether to stay or leave, but whether what success means to you has changed along the way. Either way, it helps to understand what’s really keeping you there, what’s making you consider leaving, and how much each of those things matters to you now.

No one has a crystal ball, but it’s worth considering what might change naturally over the next year or two, and how that could affect things. Could a different role, level or part of the organisation give you more of what you’re looking for? What might be available elsewhere that you’re curious enough to understand better, without needing to make any big decisions yet?

Getting clearer on the trade-offs may help you feel more certain about staying exactly where you are, or understand better what matters enough to make leaving worth it and what you’d need from your next role.

That seems like a pretty good reason to think about what you’d be packing into that suitcase.

P.S. If you’re currently going round in circles about whether to stay or move on, my free Career Clarity Compass might help you unpick what’s keeping you stuck.