career advice May 16, 2019

Back when I first moved to Colorado I landed a position at a local nonprofit. It was a fantastic fit at the time and the lessons I learned at this organization, I still carry with me.

It was here where I learned how to manage a very heavy workload and multiple competing priorities. I had 4 extremely busy people to manage and they all had different ideas of what my role entailed. Navigating and strategically negotiating these expectations was a big part of my role.

I also had outward-facing responsibilities to our constituents and became heavily involved in development and fundraising. This role was my “trial by fire” in terms of time management. Here’s the deal, I loved every minute of it! My role was weird (I managed crypts, yes, you read right, crypts) and interesting. The people I worked with were equally weird and interesting!

Do you Know When to Quit?

Then things began to change. The equivalent to the CEO left, and subsequently everyone else I had grown to admire and enjoyed supporting left. I ended up assisting people who weren’t as invested in me as a person and were only after what they could get from me.

Ever the optimist, I kept waiting for the work situation I had previously loved to return.

It. Never. Did! It just kept getting worse and worse to the point I would go home in tears regularly and landed in the hospital a couple of times. Yeah… it was that bad!

I had stayed too long. Thankfully, I now know better! Check out this video to hear my advice on when to leave.

Check out the video:

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Check out the Transcription:

Hey guys. I'm Annie of We are in the middle of a series all about how to steer your career. So far we've talked about how to figure out what it is you actually want in a long-term position and then how to get there, so how to follow the breadcrumbs in your current roles or past roles and then how to leverage that experience in order to get where you want to go.

Today we're going to be taking a bit of a different spin. Today we're going to be talking all about how to know when you should quit your current role and take on a new position in order to advance in your career. There are a couple of scenarios in which I think it's really helpful to leave your current position and look for a new role. One of those scenarios is that you've milked the learning potential from your current role to its max.

You've leveraged what you want and you've asked for more responsibility in those things that you enjoy doing. You're just maxed out. There's nowhere to go in terms of learning and growth potential. This can happen for one of two reasons. Either you're really, really comfortable in your role and you've been doing it for many years and you're just cruising along and you're not learning anymore because you've learned all there is to know in your current position and there really is no learning potential, or you're considering what would be a good tool to put in your tool belt. You're considering those things that would really help you with your long-term goal of what it is you want for your career.

By long-term goal, it could mean anything. For me I know I really wanted a position that would pay me well and I knew I wanted to work one on one with just one executive. I didn't want to support a team, but maybe that's not you. Maybe you are more into overseeing a staff of administrative assistants and administrative professionals or you love supporting multiple people because it mixes things up. Whatever that ideal position is for you, what I mean when I say when you quit your job to look for a new position, you need to be mindful of that ideal position that you have in your mind.

If you're unsure how to get to that, to know what it is that you want long-term, last week's post I go way into detail on how to figure that out for yourself. Back to what I was talking about before, you've milked the majority of your learning potential out of your current role or you notice that there are some tools that you want for your tool belt for the long-term goal of your ideal role and you're not getting it in your current position. There's just no way to even obtain it.

That's one scenario. You've tapped out learning potential and that's one good reason to leave your job and look for a new position. Another good reason that I know, but that also comes with a, not a caveat, but a word of caution is that you are not being treated you need to be treated in your current position, or the way you'd like to be treated in your current position. To be clear, I'm not talking about being reminded or reprimanded of a mistake or being coddled in any way, I'm also not talking about other people's anxieties or personalities. I'm talking about being belittled, talked down to, dehumanized, undervalued.

There's no situation in which those behaviors are okay. I would definitely and strongly suggest that you look for a new role if you find yourself in this scenario. A few years back, I worked at an organization and there was this huge changeover in leadership and I went from being respected and heard and valued to being completely the opposite, undervalued, pushed around, belittled, not listened to. It was terrible. I think I stayed too long in that position. Anyway, in both of these scenarios, either if you're not learning or if you're being treated poorly, it's time to go.

Here are the steps I would encourage you to take. I would say to plan your exit and your next position before you leave. Especially in scenario two where you aren't being treated well, it can be very tempting to take whatever comes up. I will take whatever job comes up that is not this job because I'll be treated better, hopefully, or I just need to get out of this role. Or to completely quit without actually considering what your next role is or what you want your next role to be or without even having a job.

Those are two things I would watch out for when you decide to finally leave your current role. It's not going to be easy and it's not going to be fun, but I would definitely suggest that you only look at positions that will advance your career and take you one step closer to where it is you want to be in your career. I know for me it took me a couple of positions to land in my current role, but I knew that I only wanted to support one executive. I knew I needed to be paid decently. Now I have that role that I really enjoy and I work really closely and also handle lots of personal things for my executive, which I wanted.

I know a lot of people have different preferences. Whatever your preferences are, get clear on what those are. Like I said, last week I talked a lot about how to get clear on that. Then really make sure that this next position, even though it may not be your ideal position, is taking you one step closer to your ideal role. Okay. My last piece of advice for you guys is to leave respectfully and with class. I actually gave a resignation letter to that awful job a few years back. I actually wrote a resignation letter and I explained exactly why I was leaving. I explained that I'd been treated poorly, but I did it in a respectful way.

Make sure that you are leaving respectfully. People talk and even though you think that it may not affect your current, or your next position, it will. It could, potentially, because if they call for a reference or even people know each other. I know I work in the venture capital world now and everybody knows everybody. If I want to continue to work in VC, I'm going to have to make sure that if and when I leave, I don't ever, ever see myself leaving my current role, but if and when I do, that I'm leaving respectfully so that in case people talk, it's not going to disrupt me or hurt me in any way.

Especially like nonprofit, that's another example of a close-knit community, in community. Just be aware of those dynamics and leave with class. Also, you don't owe anyone anything. If you don't feel like you can let people know why you're leaving respectfully, then don't let them know at all. If you can't do that in a way that feels good to you and that's not just like sticking it to the man, that is actually positive, then I would just be as vague as possible during your exit interview, be as vague as possible when explaining to other people.

Those are my best tips for knowing when to leave a job and then a few tips for how to leave a job. I hope you guys found this helpful. If you did, please feel free to share this video or to leave a comment below or to pop me an email at and let me know just how your experience was leaving a job and if you actually considered your next position and your long-term goal when you left your job. I hope you guys have a great rest of your week and I will talk to you soon.


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