Should I stay or should I go? How to decide when it’s time to switch jobs

I’ve been giving this a lot of thought. The topic is somehow almost taboo. It comes up a lot in the hundreds of conversations and email exchanges I have with some of the most excellent top notch professionals figuring out what to do with their lives and how to go about it.

There seems to be a lot of stigma around leaving a job, particularly when at the surface everything seems to be acceptable. There’s always a little cloud hanging over it. On top of that, on the other side of the coin, founders or managers often take it personally when an apparently loyal employee decides to move on. But let’s face it, there are many good reasons to go. Some reasons can be avoided, others can be fixed. But sometimes, the reality is, there are situations that can’t be fixed or don’t need fixing. The important thing is to reflect well on the reasons and the takeaways. So stop beating around the bush and face reality.

NOTE: I firmly believe that at work people should neither be selfish nor selfless. No matter how committed, passionate and driven you are to make things happen, ultimately, you should feel like you’re doing things for the right reason: for you!

I. Misalignment with the direction the company is going. This could mean that you don’t feel comfortable with a number of things. For instance, you don’t agree with the growth strategy, product roadmap, team structure or restructure, resource allocation, culture, etc. It could also be that you once believed and were inspired by the company vision, but you have either lost faith, or believe that the direction the company is heading in is actually mismatched with the actual vision it’s pitching. These is actually not uncommon. Oftentimes, companies have to pivot and therefore their visions evolve. You either evolve with it or you fall back. Or it might be that the vision that leadership is pitching doesn’t look anything like what’s happening under the hood.

If you’re not the type to let the current take you where it may, you will first try to drive change within the company, try to fix what’s broken (according to you) and realign it. This is great, especially if the company needs help getting on the right track.

But there comes time when it’s clear that you cannot change things. It’s ok to accept that. It’s healthy.

In fact, if there’s a clear rift between you and where the company is going, it’s best to step aside. If you stay on, you will be unhappy, you’re likely to make your colleagues unhappy, you won’t bring much benefit to the company. Most importantly, you’ll stifle your own growth and potential somewhere else. It’s a natural time to go!

II. This next one comes close to the first: a falling out with leadership. This could happen for a number of reasons. For instance:

  • Reporting to someone who you don’t identify as a clear leader. Essentially, you don’t think your manager is inspiring or qualified to lead the team.
  • You feel like you have entirely different and even opposing principles. This is a biggie. Having entirely conflicting principles with your managers, will wipe out any motivation. There’s no way you’ll be able to drive the company forward with a conflict like that. And you’ll spiral into a fixation on all of the disagreements.
  • You feel that your growth is stifled because you’re reporting to a micromanager.

Again, I firmly believe in talking things through, especially if you feel strongly about the company. It’s important to feel like you’ve at least made an effort to reconcile important differences. But if things don’t change or if you’re trying to change the unchangeable, best to accept it and move forward.

III. Losing responsibilities or losing your place. It’s important for people to feel fulfilled professionally, no matter what the role is. If you join a company that later experiences internal changes, pivots to a different business model, etc., sometimes your role will also evolve. This can work both in your favor or against you. If these changes begin to shave away your responsibilities and leave you with a role you wouldn’t have wanted in the first place, it’s time to speak up. The organization will either be able to react and redirect you into the right role, or it will mean that things have evolved to the point of “it’s time to move on.”

Reality is such. Accept it, own it, and be proactive to move forward elsewhere.

IV. You’re feeling undervalued or underpaid. This could mean not getting any recognition for your work internally, either in the day to day feedback, in the quarterly, bi-anual or anual reviews or…well, in your pay check. In all scenarios, if you feel like you are undervalued, you should make that clear. Just be profesional about it and ask for specific feedback.

If you feel like you should get a raise, bring that up as well. Keep in mind that asking for a salary review doesn’t mean you should or will get one. Perhaps the company values your position in a specific salary range and cannot raise you further in the role you have. You can either try to grow within and justify getting a raise, or you can seek to grow somewhere else. Be pragmatic.

V. You’ve come to a crossroads as they say. Professionally, you feel like you need new challenges, because you too, as a professional can have experience a pivot or grow into a new phase in your life. This might be taking on new responsibilities, learning new technologies, or changing departments entirely.

When you feel like it’s time to tackle something new and you’re starting to feel bored, you’d better act on it. If not, it will eat away at your day-to-day motivation and eventually, it will impact the quality of your work.

That’s very easy to pick up on externally as well. While at first there was no one but time to blame for the situation, if you start slacking off because you’re bored and do nothing about it, that’s on you. Avoid reaching that point.

If you feel there is room for this growth within your company, by all means, raise your hand, organize some meetings, share your interests. When a company gives a loyal (and high performer) employee a chance to evolve within, there’s a good chance it will work in everyone’s favor. It’s like a small re-birth if you will; an injection of energy, a new beginning, without losing the knowledge s(he)’s already acquired.

But that’s not always possible. There’s not always room for growth within a company. Maybe the timing is wrong or maybe, after some consideration, the company doesn’t think you’d be the right fit for the new role you’d like to step into. That’s fine also. You’ve got a right to evolve, and so does the company. Business is business. The most important thing is that you do something about it.

VI. Lack of confidence in the company’s future. If you’ve lost confidence in the future of the company, if you feel like there’s too much instability for you to handle or there are financial issues, consider looking for a new home. This is very subjective of course. I’m not suggesting you leave because there are financial issues. If everyone left every time there was a storm, no company would survive! Thank god for the people that keep pushing forward.

I’m suggesting you leave if you have lost confidence and feel insecure about staying on. Asking someone to push forward until the end is totally fine, if their drive is stronger than their fears. If they can assume the financial risks involved. But not everyone has that luxury. If you feel uncomfortable, it’s best to get away and redirect your energy.

VII. Sometimes it’s as simple as, it’s just time to move forward. It’s a hard one to explain, but don’t tell me you haven’t been there. There’s no violent separation or a struggle, there are no regrets or complaints. It doesn’t mean you’re unhappy.

It just simply feels like you’ve given your best and you and the company have come to a place where both need something new.

The company might need fresh ideas. And you might need a change of scenery, a new product, someone else to learn from. Basically, this is a reason the generally can’t be avoided, it comes naturally. You’ll probably notice yourself casually looking at job adverts, visualizing yourself working on new problems, getting a bit of that excitement and anxiety thinking about pitching yourself for the role at an interview. Don’t eat yourself up for it, go for it!

VIII. Y0u’re ready to start your own gig. This doesn’t mean you’ll be good at it. But you’ve got the bug, you’ve put your mind to it and you’ve even been working on the idea evenings and weekends. If that time has truly come, where your desire to start your own company is stronger than anything else, do yourself and your company a favor and leave. Once your heart is in a different place, it’s not good for you nor for the company. It’s like sitting on two chairs, you can’t get away with it for too long.

In conclusion…

From what I’ve found, the day to day takes over and we don’t reflect on these triggers until things get out of hand. There’s a kind of underlining guilt about leaving, when you’ve been so committed in the past. Or a tendency to blame someone or hold a grudge. In the end, why stay somewhere where you’re clearly not giving your best or getting the most back. It’s better to be doing what you feel driven to do. Everyone wins! There shouldn’t be any stigma about it. There’s nothing I hate more than people who complain, but do nothing about it when they actually can.

I think it makes much more sense to approach things in a purely practical way. No hard feelings. Think about what you can give as a professional, what you want to achieve and how you can get there. Be open about it. Put all the cards on the table. And then do what it takes to get there, inside your company or elsewhere.

If you’ve done your homework and you’re still having trouble coming to a conclusion, by all means, get in touch — hello@bliss.ventures. Bliss.ventures works specifically with digital startup talent. We definitely don’t have all the answers, but we can help you think through the factors and possibly offer some options.


For founders…

If you’re a founder, this goes for you as well. Be pragmatic, get the most out of the talent you have. It’s the most important part of your business, by far. Of course, yes, you should always think about retaining talent, but only when it makes sense for the company to retain it. That’s not always the case. Retention as a metric alone is totally useless (another interesting topic for a future post). Don’t ignore the problems. Face them. Adjust. Optimize.