If you’ve ever tried to support someone who feels stuck in their career, you’ll know it can be a delicate situation to navigate. You want to help, but you don’t want to say the wrong thing. You want to encourage them, but you don’t want to overstep. It’s easy to fall into the trap of saying something well-intentioned that ends up doing more harm than good.

It can also be frustrating (I wrote about this being one of my biggest frustrations in my post - Your Career is Your Responsibility), because you want to see your friends and family happy and successful. So when they are stuck, and seemingly going around and around it is tempting to step in and try to solve all their problems. 

But this isn’t so easy. When it comes to change, you have to be ready, it’s a process and it can’t be forced. 

So, how do you navigate these conversations with care? Here’s a guide from my experience, on what to say - and what not to say - when someone you care about is struggling with their career.

What Not to Say

Let’s start with the common phrases that, while often well-meaning, can unintentionally discourage someone who’s feeling stuck:

1. “Why don’t you just quit?”
   While this may seem like a logical solution, it can come across as dismissive of the complexity of their situation. They may feel trapped by financial obligations (which many people never talk about), fear of the unknown, or uncertainty about what to do next.
2. “You should be grateful - you have a job.”
   This phrase can invalidate their feelings. Just because they have a job doesn’t mean they’re fulfilled or happy, this statement also reinforces the “societal group-thing” mentality. I am a firm believer that gratitude, ambition and a fulfilling career can coexist. 
3. “Have you tried [insert your idea here]?”
   Throwing out solutions too quickly can make them feel like their struggles are being minimised. It also shifts the focus to your ideas rather than helping them process their own thoughts.
4. “You’ll figure it out.”
   While this may seem reassuring, it can come across as vague or dismissive. They may not feel equipped to figure it out on their own, which is why they’re feeling stuck in the first place.

What to Say Instead

Now that we’ve covered what not to say, let’s talk about how you can express understanding and empathy in a way that truly supports them:

1. “I’m here to listen whenever you want to talk about it.”
   Sometimes, they just need to vent. Letting them know you’re available to listen - without judgment or unsolicited advice - can be a huge relief. 
2. “That sounds really frustrating. How are you feeling about it?”
   This shows empathy while giving them the space to share their emotions. It also shifts the focus back to them rather than jumping in with solutions. 
3. “What would a better work situation look like for you?”
   This question encourages them to think about what they do want instead of focusing solely on what’s not working. It’s a gentle nudge toward clarity without being pushy.
4. “How can I best support you right now?”
   Rather than assuming what they need, this question lets them tell you how you can help - whether it’s listening, brainstorming, or just giving them space.

Asking open questions (ones that don’t have a “yes/no” answer) is the key to success here. It prompts reflection and a space for them to share. 

Practical Ways to Support Them

Words are important, but actions can also speak volumes. Here are some practical ways to support their career exploration without taking over:

1. Share resources thoughtfully
   If you come across an article, podcast, or book that feels relevant, share it - but frame it as something they might find helpful, not a solution they must try. For example:
   “I came across this really great tool that is a great place to start if you want more from your career called The Career Clarity Compass, it might be helpful”
2. Tap into your network
   If they’re exploring new opportunities, you can offer to connect them with people in your network. Just make sure to ask first: “Would it be helpful if I introduced you to someone I know in that field?”
3. Encourage small steps
   Big career decisions can feel overwhelming. Encourage them to start small, like attending a networking event, updating their LinkedIn profile, or exploring a new skill through an online course.
4. Be patient
   Change takes time, and progress might not happen as quickly as you’d like. Be patient and resist the urge to “check in” too frequently, it’s their process, not yours.

When to Step Back

As much as you want to help, it’s important to remember that their career journey is theirs to navigate. If you find yourself becoming overly invested or frustrated by their lack of action, it might be time to step back.

Offer your support, but let them take the lead. They need to feel empowered to make their own decisions, even if that means stumbling along the way.

Final Thoughts

Supporting someone who feels stuck in their career is less about solving their problems and more about being a steady, empathetic presence in their corner. The right words and actions can make a huge difference, but so can knowing when to step back and give them the space they need.

Sometimes, the best way to help someone grow is to trust that they’ll figure it out, in their own time, and on their own terms.

Always with love,
Elsa x