Do I Stay or Do I Go?

I'm at a loss what to do and would love some perspective if anyone has any similar experience. I can't decide if I should leave my job or not. The pay and the freedom are really fantastic. However, I just had my annual review and my boss totally blindsided me with his perception of my contribution to the company.

Now, I understood the feedback and I can take criticism and agreed that I completely recognize that I do have things to work on in terms of balancing all of the components of my job. I work in-house for a growing vacation rental company. I was employee #3 and started out by helping with reservations, operations, and doing what I could in terms of marketing when there was still time left. I cover a lot of areas and we continued to grow as a new company. I adapted to everything they threw at me. I thought I was see as a valuable asset with my wide variety of skills and roles I held here. I now am more focused less on day to day guest operations but I still fulfill duties in marketing as a one-person team, do back-end operations, and now they said I am supposed to take on project management tasks. My boss stated that due to one very large project going on for 10 months when he wanted it done a long time ago that he wasn't seeing my value in the company and doesn't know what I do all day if I didn't manage to get this project done. (The project was huge and ever-evolving with his specific requests. There is no software that exists currently to fulfill everything we are looking for). I understand I should have been more clear that's why it was dragging out. But here we are. I brought in $300k in revenue with ads I ran.

I self teach everything because my boss has never actually held a job in digital marketing. I feel like I have to explain my own job every time I see him and that I'm just flat out not going to learn anything with this mindset and having no one else to learn from. Am I just taking this review too personally?

I'll add that he ended the review with still wanting to pay me more. They are having me structure my own commission rate and want it to exceed my pay from last year. Does he value me or not?! It's driving me nuts. I feel extremely confused.

It sounds like your boss isn't very good at feedback in a timely manner. I find that a good boss provides that feedback as it arises, not just during an annual review. Your boss may be good at other things but overall people tend to leave bosses, not companies. Ask yourself if others at the company have the same mentality or they are more open to positive and negative feedback throughout the year? Freedom in a job is a big plus but what is the overall culture? If you align with that culture I wouldn't jump ship just over 1 bad review. He may have also not seen it as that bad if it ended with you getting a raise! Remember, you are your own worst critic. I would start by telling your boss you understand his concerns but would like feedback on a more regular basis so you can course-correct before it's too late. Hope this helps!
I really appreciate you taking the time to reply. I definitely agree that I should not be blindsided in a review and wish it had been brought to my attention earlier. I have been here for 4 years so I am definitely not trying to jump ship due to impulsivity and I can be especially hard on myself.. so thank you for reminding me we are often our own worst critics. I will definitely make it known that I would like more regular feedback instead of him just piling it up and waiting for this one day out of the year.. Thank you again for your response!
I’d say there are challenges here on both sides. You admit you didn’t communicate well about the project but your boss also didn’t communicate his feedback on time.All in all though, it sounds like you’re more upset and entertaining leaving due to that. But one bad review isn’t a reason to leave on its own. Is your boss a terrible boss? If so that’s a separate thing to consider and could be cause for leaving. But otherwise you sound like you enjoy the other parts of your role and are well compensated. Also, relationships with bosses evolve and adapt over time based on mutual feedback. If your boss is open to changing that’s very helpful but he’s not just going to guess this on his own, you have to communicate your requirements to him too as his team member.In short, it sounds like this is one bad review with things to learn on both sides, not an immediate reason to leave it all and go.
Thank you for responding :) That is very true, I think we both made mistakes in not communicating to each other when it was needed. He is not terrible, but just a difficult person to work with. I feel like he tries to act like I am not an authority figure on anything even though he has less experience in the digital marketing realm, which is where most of my tasks are falling right now. I feel like I can healthily give feedback without him just saying "just get it done". Which is frustrating but I've dealt with it for 4 years now. You are correct in that I also need to step up and communicate it more even if just to have these updates in writing.
Knowing you value the pay and freedom your job provides, my inclination would be to run a "pilot" over the next few months to see if you can get your current situation to a more tenable place.You could quit instead. But I'd recommend starting here because (a) you like two very important facts of your job and (b) I see this as a two-way communication failure as much as a one-way management failure.In particular, I'd suggest approaching your boss and saying something like:--> Frame the concern: "Candidly I was surprised at the content of our annual review. I believed I'd been focusing on the highest-value things for the company over the last year so I was concerned to hear that wasn't your take away."--> Articulate your view of the problem / situation analysis: "I think part of the problem is that my role has several components and we may be weighting the importance of these components differently."--> Convey you are solutions-oriented: "I'm viewing my job as X% guest operations, X% marketing, and X% project management. I'm weighting toward Y because you'd mentioned a top priority for the business is Z and I view this as a crucial lever." (Then wait to see how your boss responds - maybe you'll hear you're not prioritizing correctly! But where you should hold the line is on your ultimate capacity. You can not do three things at 100%; you need to make your boss understands that increasing investment in one thing also means decreasing it in another.)--> Communicate you understand and are working on your weaknesses: "I realize there have also been some things on my end I need to improve on, including communicating status updates and blockers. Are there other things I should work on to make sure I crush it this year?"If your boss is on board with your approach after this conversation, then it's on you to continue updating your boss as your priorities and projects develop. Consider sending them a weekly written status update on your projects and priorities in addition to live conversations; some people have a harder time holding verbal updates in their head. And then set a period of time. Maybe it's a quarter, four months, six months.... But commit to reevaluating how the year is going then and determining whether it's worth continued investment. If you're seeing improvement in your own happiness, great! If not, maybe it's time to start looking outside your company for your next role. But this way you'll know you've made an honest effort to make it work.
Thank you for your response. I really appreciate your thorough insight and recommendations. I really resonate with the comment you make about not being able to do three things at 100% because I definitely start to feel pulled in many different directions and sacrifice quality. I take pride in my work so ultimately this leaves me feeling subpar in many areas rather than really strong in one and that is something I have long been struggling with. I also really like your recommendation of status updates to have some written documentation on these projects. He often has a knack for forgetting things and shifting what he thinks happened in his head. I also think this is great to hold me accountable for not letting anything slip through the cracks. I plan to utilize your framework here in my follow up from the review, thank you! I was initially using this as one more reason to leave (there have been others in terms of feeling stagnated being a team of one) but I like the idea of giving it a try since good pay and flexibility are not always easy to come by.
Did you have problems with your boss before this review? If so, that points to a bigger problem and perhaps a reason to think about leaving, but if you felt OK before this, maybe the review just hit a little too hard. I agree it could be helpful to ask your boss for feedback more regularly. Perhaps you could schedule a follow-up conversation with him and express your concerns about the review and figure out a way to work better together going forward (including more regular check-ins/feedback). It does seem like if he gave you a raise, he sees the value you bring to the company.
I have historically had thoughts of leaving mostly because I feel like I might be stagnating in terms of being able to advance in my skills and learn more. Having him question everything I do was just one more piece to support that fact. It's been hard covering all areas as a one-woman team. I definitely plan to ask for feedback more regularly to avoid this again in the future, though. Thank you so much for replying!
Hi @Katyy, When deciding about quitting, consider a few things:- Role -- what % of your day to day work or projects aligns with your workstyle, strengths, and natural tendencies?- Industry -- how aligned do you feel with the product/service that your company produces? do you feel that their mission is important & interesting?- Environment -- does the culture align with your personality and values?- Give yourself a 1-10 on each of these to try to assess the current state of where you're at and what to do about it.Additional resources for you to look at:-Short quiz to decide on ""should I stay or should I go"" --> minute webinar on deciding if/when to quit --> post about how you're feeling about your current role & what to do about it-->, I'm Rachel, a Career Coach (, and I offer a ton of free videos and blogs on my website here -, and also a free initial career coaching call here--
Thank you for all of these great resources!
This one is easy, every week give him a week in review email. clearly he is very disorganized and as in most startups tossing stuff at you without regard for what is already on the plate. So, definitely acknowledge you heard his feedback but also give him some, tell him what you need from him. Deadlines- time to process and deliver, and space to ask questions. If you cannot get this from him with some consistency and in the fashion that you need it then its a bigger problem and time to look. Tell him you are currently confused and need him to streamline or provide workflows for specific things if he wants it done his way. If you have freedom to deliver based upon his saying here go do this then show him how strategic you are. You get to decide if you take or give direction that way. Good luck!
I think the weekly review is a great idea. Great point that I have freedom to deliver and work on streamlining our process and communication. :)
Sounds like you're growth mindset oriented and open to feedback and change, AND, having worked at a few startups since early days, it's really common for the employee to not be a fit at a later stage in company - you just aren't an energetic match anymore. If you had inclinations to leave before, that's a hint, ask yourself what was that about? What was out of alignment? What would feel really good right now? Happy to help and I offer free coaching discovery calls if this resonates for you. Wishing you all hte best, Katyy!