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Knowing When To Walk Away

Lindsay Kelly • February 28, 2023 • Providence, RI

Summary of "Knowing When To Walk Away"

In the talk "Knowing When To Walk Away," presented by Lindsay Kelly at RubyConf 2022, the focus is on how to decide whether to leave a job that initially seemed ideal but may have transformed into an unsatisfactory situation. The speaker encourages a thoughtful and introspective approach to determining if it's time to move on from a job.

Key Points Discussed:

  • Personal Experience: Lindsay shares that her insights stem from her own experiences with job changes, emphasizing that while her advice is based on personal reflection, it’s ultimately up to the individual to determine their path.
  • Identifying Changes: She describes how a workplace can transition from a dream job to a nightmare due to various factors such as management changes, shift in company culture, or personal changes.
  • Assessment of the Situation: It's important to evaluate both external and internal changes that impact job satisfaction:
    • Consider previous motivating factors for accepting the job and assess if those have changed.
    • Reflect on what your dream job looks like now and whether your current role aligns with those aspirations.
    • Identify the scope of changes: are they temporary challenges or significant shifts in the workplace dynamics?
  • Communication and Feedback: Lindsay stresses the importance of voicing concerns:
    • Utilize the ASK principle (Actionable, Specific, Kind) when providing feedback to managers.
    • Seek guidance from mentors or trusted colleagues to discuss concerns and explore potential solutions.
  • Introspection: Reflect on personal goals and happiness:
    • Ask yourself if your job supports your personal and professional aspirations, and if it's fostering your growth.
  • Moving On Intentionally: If deciding to leave:
    • Plan your transition carefully, ideally securing a new position before quitting.
    • Handle the departure gracefully by tying up loose ends and expressing gratitude for the experiences gained.
    • Change can be daunting but is also an opportunity for new beginnings.

Conclusions and Takeaways:

  • It’s essential to be proactive and maintain an ongoing assessment of job satisfaction in relation to personal goals.
  • Making thoughtful, deliberate decisions about your career is crucial for individual well-being and professional fulfillment.
  • Positive transitions can arise from the courage to leave a less-than-ideal situation, leading to personal and professional growth.

The talk concludes with an invitation for further discussion, reinforcing community engagement and support among conference attendees.

Knowing When To Walk Away
Lindsay Kelly • February 28, 2023 • Providence, RI

Picture this: the job you've always wanted. Doing exactly the kind of work you want. Having great coworkers and management. But then something shifts, and the dream becomes closer to a nightmare. How do you identify these things happening? How do you raise concerns in an appropriate way? And as a last resort, how do you know when it's the right choice to walk away?

RubyConf 2022 Mini

00:10:880 Hi everyone, I'm Lindsay. My pronouns are she/her, and this is 'Knowing When to Walk Away' or how to decide to leave a dream job.
00:14:040 This is a topic that, believe me, is 100% comfortable to discuss and does not fill me with the least bit of anxiety. None at all.
00:19:560 In fact, I actually submitted two talk proposals for this conference and secretly hoped this one wouldn't be selected. But the fact that it was, and the presence of so many people in the room, assures me that it’s a topic that needs to be discussed as openly and honestly as possible.
00:28:920 I will do my best. A couple of disclaimers before we dive in: this is based on my personal experience and the way I went about processing a very personal decision—emphasis on the word personal. There's plenty of advice that I'm sure can be taken from it for others to use, but know that it's not my intention to tell anyone what to do with their lives. So try not to walk away from this talk thinking, 'Lindsay made me quit my job.' Instead, think more along the lines of, 'Lindsay inspired me to introspect and make a plan for what's best for me.' Then we should be good.
00:52:739 So picture this: after an exhausting search, you find yourself in an ideal role—a dream job—exactly the kind of work you want to be doing, with a supportive team, a really cool manager, great benefits, and stellar perks. You can't imagine finding a better position. But then, after some time, something changes. Maybe it's a change in management or company leadership. Perhaps the scope or type of work you're doing has changed—policy updates, benefit changes, toxic coworkers, you name it. Whatever the reason, the dream has become more of a nightmare.
01:30:749 And it could be anywhere from a jump scare, someone-chasing-you style nightmare, to just a really dull trip to the DMV. But a nightmare, nevertheless. So, what do you do now? Well, I know from experience that it's a horrible feeling to feel stuck in a job. That said, a job is an awfully serious thing to consider walking away from. So, if you're starting to contemplate whether or not a change might be the right move for you, take a breath and walk through what should be a very deliberate decision.
02:20:440 Firstly, consider what made you take the job in the first place. We all make comparisons and assessments when on the job hunt, and certain factors will determine why we choose one role over another. Consider those factors and whether they might have changed or looked different now. If leadership was a big factor in why you took the role, and then suddenly there's a big management change or a company reorganization, do you still feel the same about that aspect of the job?
02:56:739 What if you fell in love with the team you interviewed with, and then one day you turn around to realize none of those people are your coworkers anymore? What if the benefit structure was a big part of your decision to pick a role, but then that drastically changes a year later? Different doesn’t have to be bad—it’s just different. Let me be clear: just because things change at a job doesn't mean it's for the worse. There are plenty of positive or even neutral changes that can come with extended history in a role.
03:21:480 Just because a change is a positive for one person doesn't mean it's a positive for you, and vice versa. What about times when nothing has changed with your role, but you've changed? Possibly more than this sales tag. We're all learning, thinking, growing creatures, and we reserve the right to change our minds about what constitutes a dream job.
03:57:900 Maybe it's not realizing that a different option exists, or maybe it's a matter of priorities changing. Whatever the circumstances, personal changes are just as worthy of consideration as external ones. I think it's worth keeping an updated notion of what your dream job looks like—from the type of technical work you're doing to the comprehensive package being offered.
04:33:360 What does the ideal role look like to you? Don't be shy—think big! What is the Barbie Dream House equivalent of a job for you? While not every role can live up to every aspect of the dream, it's worth taking the time to introspect and think through what your priorities are. Maybe they match up with your current role better than you thought, or maybe they don't.
04:57:900 I've personally yet to find a company that offers this sort of rad slide as transportation between floors, but luckily I've got other priorities on my list checked off. So, you’ve assessed that there have been some changes since you first made the decision to take the job, or that the job and your dream scenario have deviated, and it sounds like those changes haven't necessarily been positive. Now what?
05:36:780 Start by looking at the scope of the change. There’s a big difference between an overall policy or cultural change versus a temporarily difficult project. Is the scope manageable, or something you feel you can weather? Is it something you can counteract or do something about, for example, moving to a new project or to a new team? When was the last time you took time off? It's amazing how different things can look after a healthy dose of rest and relaxation.
06:07:680 Could your concerns be addressed with your manager and any action be taken, or is the action to be taken moving on? Let's talk about voicing our concerns, a daunting task for many. I think feedback is an invaluable part of the development process, and luckily most people in our field seem to feel similarly.
06:40:799 If you've got a manager or mentor that you trust, try talking through the changes you're concerned with, and hopefully, they can help you process another viewpoint. Another viewpoint can help you feel heard and can often help find possible solutions, if any are available. If you don't feel like you have someone to voice your concerns to, well, that seems like an important consideration for your decision.
07:26:540 I have a favorite acronym when thinking about feedback that I learned during my time at Dev Bootcamp. When asking for feedback, think ASK, with a K. Enunciation is very important. That's actionable, specific, and kind. If you’re voicing concerns about something going on with your company or your team, you want there to be something done about it instead of just saying you don’t like the new coffee shop that moved in downstairs.
08:12:180 You also want to think about specific things. I think we can get caught in a trap of vagueness to try to be polite, but the more specific you can be, the more likely you are to find a plan of action. Lastly, you want the feedback you give to be kind. Even if what's going on has you hurting, think about how to voice concerns in a way that looks out for the best interest of the company, your team, and of course, yourself.
08:58:579 This acronym also works great for any time you have to give feedback, not just for impending life-changing decisions. Also, if you weren't able to attend, go back and watch Stephanie's talk about empathetic pair programming with non-violent communication. There’s lots of excellent feedback advice there too that can be applied in this situation.
09:32:220 For managers attending this talk, how can you be supportive of a coworker coming to you with concerns? While management positions and philosophies may differ, I think we can all agree it's important to be understanding and encouraging when someone comes to you with a problem. Be prepared; if there are changes affecting your team or your company as a whole, folks may have concerns, and it's part of your job to help hear them. This is not a time to try to argue or be defensive; it's a time to listen, validate, and help.
10:32:860 Remember that part of a good manager's job is preparing team members for the future, even if that future is not on your team. Back to our hypothetical employee—totally hypothetical. Now you've considered the change, how it impacts you, and any possible plan of action. If you feel good at this point, great; class dismissed. You can move forward knowing you're intentionally choosing the role you're in. If not, it's time for some further introspection. This is the time to ask yourself those cliché questions like, 'Where do you see yourself in five years?'
11:24:140 Think back to your dream job and how that relates to your overall goals. Reflect on whether this role is really supporting those goals. When I was making my choice to leave my role, I thought a lot about my goals, both personal and professional. I asked myself if the role I was in was supporting and enabling those goals. I wondered if there was a clear path for me to move forward in pursuit of those goals. I also asked myself if my leadership was supportive of those goals, and lastly, but certainly not least, I asked myself if I was happy.
12:42:040 For me, and my particular situation, the answer was no. And that's not to suggest this is an exhaustive list. There are plenty more factors and considerations that could weigh into your decision—whether or not you can financially support yourself, if company values align with yours. We could talk for hours about everyone's individual scenarios and still have more what-ifs.
13:46:560 In fact, if you're currently weighing your own decision and would like to talk it through, come find me during the conference or email me afterward; anytime—open invitation. I would be happy to talk it through with you. But for me, it all comes back to goals and how those are or are not being supported. Be honest; this process only works if you're truly and fully truthful with yourself.
14:41:709 After all that introspection, you've decided to move on from your current role. Now what? Well, again, I hesitate to tell anyone what to do with their lives, but I would recommend finding a job.
15:04:440 Sometimes there are circumstances that are toxic enough to warrant a speedy departure, or maybe you have the means to take some time off. But I generally recommend having a plan in place. Job hunting is an entirely different, lengthy presentation that thankfully I'm not giving today, but I will say that it's easier to find a job when you already have one.
15:37:360 When you're hunting, think back to that dream job and your goals. You've just done all this helpful introspection and reflection; now's the time to put it to use. Of course, choosing to move on is only half the battle, and regardless of how bad things may have ended up, actually moving on is a whole other thing. You may find yourself feeling remorse or regret, or experiencing graduation goggles—the phenomenon where things seem to take on a rosy, positive hue as they're nearing their end.
16:47:920 Having second thoughts is totally normal. Change can be scary, and our jobs are an awfully big part of our lives to alter. So let's talk about what it means to move forward gracefully and gratefully. First, make sure you tie up any loose ends at your current role. The standard protocol is still giving two weeks’ notice, but during that time it's worth ensuring that you’re wrapping things up as cleanly as possible.
17:46:180 Are there projects you need to finish up or properly hand off to someone else? Are there responsibilities you need to ensure someone else is covering? Is there specialized knowledge you have that's worth documenting? When in doubt, document it. It'll make your coworkers' lives much easier in your absence.
18:29:040 Regardless of the circumstances of your departure, it's a kindness to ensure things are handed off well, and you never know who you might meet again in a future role. Next, try to move forward with a grateful heart. There can be a lot of feelings accompanying departure from a job—sadness, relief, anger, excitement. Whatever the particular flavor, this role has been an important part of your journey.
19:04:920 Reflect on all the things you've learned and the experiences you've had; they've helped make you the person you are today. Even this experience of deciding to move on is a valuable one that you couldn’t have had without the role in question.
19:37:240 Of all the feelings you might be experiencing with this impending change, focusing on gratefulness and gratitude is probably the most productive. I generally advise a little more tact than this when delivering your news, but you know what? You do you.
20:14:700 For our managers out there, it can be hard to let go of employees, and it can be hard not to feel disappointed at losing a good coworker. This is also a time to focus on gratitude from your side. Feel grateful for the time you've had, the contributions this individual has made, and how you've grown as a leader by getting to work with them.
20:47:440 As hard as it can be to watch someone leave, if they've decided that moving on is what's best for them, then it's imperative to support that. Besides, you want people who are enthusiastic about working for your team and your company—not simply tolerating it.
21:28:639 So, to tie it all together, if something has changed and you're no longer sure if your job is the right fit, you owe it to yourself to make a thoughtful, intentional decision. Consider all your goals and what the dream job looks like to you now. Are you working towards it?
21:57:940 If not, consider the scope of the change and try to come up with a plan of action. When in doubt, seek out a manager or mentor to troubleshoot and process with. Consider all the options that exist for you. Regardless of if you choose to stay or move on, the goal is to do so as intentionally as possible.
22:54:960 And when it comes to moving on, all those cliché things they say are true, like, 'When one door closes, another one opens.' There are wonderful adventures, experiences, and interactions that await you on the other side of change; you just need to be brave enough to take the leap.
23:44:460 That is the end of my official comments, but before I close out, a few last things from me. I work as a software engineer for a company called Within3, and we are currently hiring Ruby on Rails developers. If more information is relevant to your interests, especially after listening to this talk, come find me afterwards.
24:12:420 If you'd like to continue this conversation or want to get in touch for any reason, here's my email. I'm also occasionally on Twitter, though I'm not a verified account so clearly you can't trust anything I say.
24:50:660 I'd like to open up the rest of the time for questions, so whether you'd like to know more about my experience or have any completely hypothetical scenarios you'd like to talk through, I'm all ears.
25:05:740 Yeah, absolutely! Just to restate that for the microphone, talking about times when you've left a job too late and that it's important to take action when things first get bad. I think this introspection process of thinking through where your job is related to what it was when you first started, and how you feel about your goals, should be a regular part of your process.
25:35:360 Even if there aren't any big changes that have happened, just being honest with yourself about where you are in relation to your goals. A consequence of leaving too late... Yeah, I'd add to that, you know, thinking about your own happiness is a huge component. Thinking about how your mental and emotional state is during the time you're staying on. Also considering productivity; if you're unhappy, are you really going to be doing your best work? Are you going to be contributing as much as you could be? Or is that time better spent applying yourself toward other jobs?
26:48:500 Yeah, just to rephrase that, that was to mention that if you're staying in a leadership role when you're unhappy, you're setting a poor example for others, and that could trickle down.
27:49:920 So, the question was can you say something about the importance of building up 'fu money'? Which, if you're not familiar with the concept, is having... As I understand it, just we could be talking about different things, but money that you have on standby that if the time comes that you just say 'F you, I'm quitting,' you have that padding to be able to do that.
28:51:740 So, I definitely think that's important for a number of cases—not just for job security; it's worth having some padding. This is not a financial conference talk, but I am also a personal finance nerd, so feel free to talk to me about that. But having that padding can empower you to make these sorts of decisions. Any of us living paycheck to paycheck or even close to that, being able to go through this process is a luxury, and it's not one that all of us can afford. I acknowledge that.
29:32:660 So the question was, do you have any thoughts or feelings on exit interviews? Yes, I do. I think exit interviews are becoming a more common practice. I had one in my last interview at my last company that kind of inspired this talk, and I definitely gave some honest feedback.
30:18:420 I think it's important to walk the line between, again, not completely burning bridges to the ground, but also letting your concerns be noted, especially in my case where there were concerns that I had voiced to a manager previously and then I had to restate that this is part of the reason.
30:48:660 So, if you have a background of having tried to voice them before, I think that's an especially good time to voice it in an exit interview. That's a great question; just to restate, how surprised should your employer be when you're choosing to leave? Should it be part of a series of conversations that they're kind of getting the picture of things, or do you keep your cards close to your chest?
31:40:660 I'd say in general, that's a personal decision. But I think part of trying to work to make things better includes giving feedback and trying to voice concerns early and often. In my experience, particularly, it was definitely a series of conversations with my manager and talking through things—what potential outcomes for change were or if there weren't any.
32:34:600 So when it was time for me to say, 'Hey, I'm giving my two weeks,' it was okay. We kind of knew this was coming, again I acknowledge that that comes from a place of privilege that not everyone will want to show their hand in that way because of maintaining job security.
32:55:260 So I think there are ways that you can voice your concerns and talk through things to make a plan of action without saying, 'Hey, if this doesn't change, I'm leaving.' Thank you.
33:29:220 So again, to restate that, some people are hesitant to voice concerns because of possible retaliation. What are my thoughts on that? Hopefully, you work for a company that has anti-retaliation policies in place. I think that's pretty common these days.
34:03:420 That said, that's not going to fully protect us, and it’s not always going to make us feel entirely safe. I look back to thinking about that actionable, specific, and kind feedback. Or you can look back at Stephanie's conversation about non-violent communication—some really good thoughts about how you can voice things without it being an attack, without it being something that someone would feel inclined to retaliate against.
34:51:639 Doing lots of 'I feel' statements can help ensure that it comes from your personal experience and not saying that something else is specifically bad. So the question there was, is it ever a good idea to tell your manager, bluntly, 'Hey, I'm thinking about leaving'? And I'm interviewing other places; this is where I am now.
35:53:180 I'd say yes, it can be. Again, I think sometimes having those earlier conversations that sort of build up to that so hopefully it's not a huge surprise. But having it all depends on the relationship you have with your manager and what the policies are in place.
36:58:940 I know that the manager I had at my last role, I felt comfortable, and I did tell her when I started looking elsewhere. That was done to prepare her and make sure she was well informed about where I was. However, it also was not used as a bargaining chip of, 'Hey, you better change this or otherwise.'
37:58:400 So, I think if you're coming from a place of kindness, informing her and really emphasizing your concerns that haven't been addressed, then I am open to it. But again, it’s all about your individual relationship. I hope that the managers in this audience are doing what they can to be open and respectful of anyone trying to voice that.
39:07:140 Alright, well that's unfortunately all the time we have. But again, if anyone would like to continue this conversation, please come and find me at any point during the conference. Thank you all so much for your active participation. I really appreciate it.
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