How to Be a Good Friend to Someone in Work Transition

Work is hard. If it was easy, we'd call it something else. Life can also be hard. For ourselves, and for others. We spend lots of time at work - certainly more time than we spend at home or with our partners. Life happens outside of work, and there is also a lot of life that happens inside of our working environments. With all of this time spent and emotions felt, invariably, at times, things are going to get tough.

That's why it is incredibly important to know how to be supportive to the important people in your life who are currently going through a tough work transition - because hey - you might need some support later down the road too.

Of course, every relationship is different, every person is incredibly different. It would be impossible to write an article about supporting people who are going through a tough work transition that would pertain to each and every type of transition, or to each and every type of relationship. So instead, I am going to write with broad strokes a couple tips that should act as a good barometer of how to support someone who is going through a tough time when it comes to work.

One caveat: this article will be most helpful to those looking to support friends and family members that they do not currently work with. This is an important distinction, as when both friends work at the same company, it can become easy to make a bad situation worse the more that both parties focus on it. I recommend that if you both work at the same company, that you take my advice with a grain of salt and seek the help of a trained HR professional or employee assistance program instead.

How To Support Someone Going Through a Transition at Work


Step One: Realize that not everyone feels the same way about work that you do.

Each person’s dreams, desires, and motivations when it comes to the world of work are going to be different. So before you launch into a conversation about what they could do to improve their situation, try and figure out where they might be coming from.

Step 1: Realize that not everyone sees work the same way you do.

This seems like such a stupid thing to write, such a "duh, I knew that," moment. But it's actually really important. Let me explain why.

Here's the deal - not everyone sees work the same way you do. We all have different values, different things that motivate us, different things that make us get up with a sense of appreciation and excitement in the morning. Conversely, we all have different things we hate, different things that make us feel discouraged at work, and different things that make us feel trapped, depressed, or down about our work or our life. Before you can be a good friend to someone who is going through a tough time at work, figure out where they might be coming from. Are they in their late fifties, and ready to retire, but afraid of what that means monetarily and feeling stuck in a job they hate? Or are they young, relatively inexperienced, but with tons of passion and a real desire to grind it out and succeed, but feeling stymied by their lack of credentials? For both people, what they do for work and how they do it is incredibly important to their sense of meaning and identity, but how that meaning manifests itself in their actions and in their feelings about it is going to be incredibly different. Each person's challenges, dreams, and desires are going to be different. So, before you launch in to a long conversation with them about their feelings or attempt to do something nice for them, really try and figure out what they might be feeling and where they are in their unique work journey. It's probably different from yours. This will be a crucial step of reflection and empathy that will make the difference between your support lifting them up or making them feel even more discouraged and alone.


Step Two: Be Ready to Discuss Things About Work that are Not So Rosy and Cozy.

Your friend needs to be able to discuss their feelings about difficult things in an environment where they feel accepted, loved, and free from judgement. Prove that you can listen to hard stuff with grace and you’re already halfway through your journey to be a good emotional support.

Step Two: Be Comfortable With Discussing Things About Work that Are Not So Rosy and Cozy

This feels like an odd thing to write on LinkedIn, a site that is all about the "hey, look at me being awesome and killing at life" part of work. This site encourages us to share our wins, our promotions, our awards, our launches, and our accomplishments with the world. And that is awesome! But let's just call a spade a spade and say that we all know it's not the only side of the work story. Sometimes I wish LinkedIn would let us share work horror stories, bad-boss melodramas, or gripe about corporate events where we are simply forced to just drink the kool-aid and suck it up! That would feel a bit more authentic to me, and also to a lot of people I know. But that would be off-brand, and it's never going to happen, so I digress.

The fact of the matter, is that sometimes our work life, just like any other parts of our life, can really suck, feel incredibly difficult, or be incredibly confusing and stressful. People have bad breakups, bad marriages, bad travel experiences, bad days, and unfortunate events all the time that make them sad, make them confused, make them feel overwhelmed, or make them just plain pissed. It's a part of being human. Work is no different. And even the best jobs, marriages, travel experiences, days, and events have their own challenges and weak-spots within them. Again - just a part of life. The difference is for basically all parts of our private life, we have everyday safe spaces in our society to gripe, complain, commiserate, or let off steam about them - except for when it comes to work.

I don't know why we don't have the same number of real-talk safe-spaces to discuss the unique challenges in our life as they relate to work in America, but it is true. Perhaps it is our protestant roots, or the fact that as a society we celebrate hard work, value achievement, and fear the idea of missing out so much. Even more esoteric of an idea, but still a valid one, is that perhaps this intolerance for dissatisfaction at work is part of being in a capitalist society that rewards individual gains and is always full of winners and losers in equal measure, so if you're currently on the losing end - then, whatever we say! Figure it out! We don't want to hear about it!

All reasoning aside, if you truly want to be a good friend to someone who is going through a work transition, you need to be comfortable with discussing the parts of work that can be less-than-enjoyable. The difficult office relationships, the discouragement of job-seeking, the fear of retirement, the stress of overwork, and on, and on. Whatever your friend is going through, if you truly want to help them, you need to be ready and willing to listen to, and give advice on, the things about work that are difficult - horrible even - for them. And you need to be able to do so in a way that is accepting, loving, and free of judgement.

There's definitely a sort-of "la-la-la-i-can't-hear-you" thing we get when we start talking about things that are difficult for us at work. I get it - no one has time these days for anything - especially when it comes to other people's problems. But your friends and family are different, and you should treat them different. With more compassion and a willingness to listen and really give thought to how you support them during this time. It can be difficult for people who are going through a work transition. The lack of time they get to talk about these feelings or challenges can make them feel uniquely wrong and alone, and even more discouraged because they feel like people either a.) don't care about what they are going through or b.) care, but really don't want to talk about it. If you can be the type of friend who can prove that you do care, and that you do want to talk about it with them, and that you will support them - then you are already halfway there on your way to being a good support during their time of transition.

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Step Three: Offer Ideas and Advice

Caveat: the solution you propose needs to be realistic, attainable, and individualized.

Step Three: Be Able to Really Listen Without Judgement, then Try to Offer Something Truly Constructive, Positive, or Useful When the Moment Feels Right. Caveat: the Solution You Propose Needs to Be Realistic, Attainable, and Individualized

Once you've started really listening to your friend or family member, they'll begin to go deeper with what they share with you. Be prepared for some heady stuff. Don't feel like you have to process it all at once or know exactly what to say all the time. You don't. They are just letting off steam. There might be a lot built up, because most people won't talk with them about it. And remember that a rushed response is worse than a considered silence when dealing in emotional territory. When someone goes quiet, it just means they are thinking, and that they care about what they are going to say. It also helps the speaker gather their thoughts. There is nothing wrong about long pauses. Think about how what you are about to say will be perceived as well. Don't be afraid of emotions, and let your friend be themselves when you talk. It also goes without saying that you should avoid all attempts to control, criticize, judge, or offer platitudes. And when the moment feels right, that's when you can give some considered advice.

This advice needs to be based on real things you have actually thought about for your friend, not just a rushed platitude. When thinking of ideas to bounce off of your friend, make sure your solutions are:

1.) Realistic.

2.) Attainable

3.) Individualized.

You want your ideas to be realistic because they need to be things that person would actually be able to do and implement. They need to be attainable because they need to be goals and targets that could be implemented and executed with a reasonable amount of time and money. Your ideas need to be individualized because the things you suggest need to be relevant to your friend's lifestyle, interests, experience, and means. Also, notice how there are no "Should's" anywhere in this article yet? Yeah, that's for a reason. No one wants to hear what you think they "should" do when it comes to their work or job. Remove that word from your vocabulary, and remain vigilant while talking with your friend to ensure that your words sound empowering, not condescending.

For the truly important people in your life, make lists or write down some ideas ahead of time (before you talk to them or see them next) full of ideas or thoughts you had about how they could make this whole situation a little bit better for themselves. Do a big brain-dump, then edit out things that don't seem right later. You'll walk away with some good ideas to percolate on. Sometimes people just need to hear ideas from someone else that's not in their head to give them a whole new perspective on things. This forethought will really make a difference, because it will show up in the kinds of things you say, as well as how you say it. Don't be surprised if after making a list or writing a journal entry about your friend's situation and sharing your ideas with them the next time you talk, that they say something like, "Well, I never thought of that. Thanks! That's actually something I could do. I will think about it." That feeling is pure gold. Even if they find that they don't pursue that exact course of action, it starts opening their mind to a new train of thought that can help them get un-stuck.

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Step Four: Avoid Going Down a Negative Rabbit Hole.

You’re going to be talking about challenges, so make sure you are offering solutions.

Step Four: Avoid Going Down a Negative Rabbit-Hole Where You Only Talk About Problems. Talk About The Problems, But Bring it Back to Future-Based Solutions.

With all this talk about problems and general dissatisfaction, it would be incredibly easy to start taking a long-winded trip down to negative-land with your friend. You want to be extra careful that in your effort to help them process and problem-solve their work difficulties that you don't end up making them (or yourself for that matter!) feel worse about it. Stay focused on solutions and the future whenever possible, instead of thinking about the past, or on problems. The future is a fun place to play - it hasn't been written yet, and your friend can work toward their future every day. Be careful to not spend much time on the past. Regret is not a fun theme-park ride. Riding the roller-coaster of regret is like the worst roller-coaster ride ever: you know exactly when each twist is coming, each time you go down it the feeling is more painful, and once you step on the ride of regret, you can't get off. Ah! No thanks! Conversely, the future is a very fun carnival ride. We don't know what's ahead, but we can strap in, take a deep breath, and always choose to be optimistic about what we might see around the corner. Be aware that during the transition period that your friend is going through, they will probably be a little less chipper about things than they usually are, and you might have to help them see that bright future with your positive talk. It's very normal when going through a work transition to feel extra insecure, negative, hopeless, even trapped. Be ready for these feelings from your friend, and they won't surprise you. In fact, expect them, and arm yourself at the ready with a lot of positivity to back it up. Make sure that when your friend starts going down to a negative place, or hopping on to the roller-coaster ride of regret, that you take their hand and bring them to the fun ride of the future!


Step Five: Give Lots of Compliments

What we hear about ourselves from others forms the backbone of what we believe about ourselves, and who we believe we can become. Point out to your friend the things that make them unique and you’ll build their confidence as they figure out what is next.

Step Five: Tell Your Friend Regularly What Makes Them Great, Unique, and Special

When a friend is going through a work transition, they are going to feel unsure about themselves as well as what's next. Make sure that in ways big and small you look to say things that build them up. Make your "Bob-the-Builder-Upper" comments be something simple, authentic, and specific. Don't say things that are un-true, just to compliment them, as people see right through that and it's just not the right way to be a friend. But something as simple as; "Wow, I love your outfit today! You're so creative with how you put things together, it's a real skill," could be a game-changer in lifting their spirits. Are they incredibly regular with their daily walk routine? Compliment their discipline. Are they a whiz in the kitchen before family dinner? Tell them how awesome it is that they spend time focusing on nourishing others. I think that these little compliments we hear about ourselves from those we love most form the backbone of who we believe we are and who we believe we can be. When you compliment someone on a skill or a trait or something else special, I believe you are giving them a rung on a ladder to step on as they climb toward their next chapter. Compliments sound small but they can really make a big difference.


Step Six: Check in Regularly

You can’t give compliments, offer advice, or be a listening ear if you don’t call your friend or see them. So reach out and stay in touch.

Step Six: Check in Regularly

You can't give compliments or advice if you don't talk with your friend or see them. Another thing to note about people when they are going through a tough time at work: they tend to self-isolate. Think about it: does a wounded animal lick their wounds in public? No. They go back to their dark, warm, den and do some serious self-care. Or brooding. Or both. Your friend is probably not going to reach out to you. Sorry. It's just the way most humans tick. So you might have to be the one calling, texting, or emailing for a little bit until they get out of this funk and into the next chapter of feeling good. Don't take it personally.

The best ways to get in touch are high-touch avenues. You're not really doing your friend any good if you are just texting randomly or messaging them on Facebook every once in awhile. Sorry. So make plans to get together, stop by their apartment and ask if they want to get a beer if you know where they live, or pick up the god-damn phone and actually place a call. Once you've done that and are regularly seeing them, then texts and Facebook messages are a nice add-on, but that kind of interaction is the frosting - not the cake. Make it a point to call or see your friend once a week, and make these visits high-quality time where you are not looking at your phone or are otherwise mentally half-in, half-out. You gotta be fully present.

(Note: For people who live across the country and cannot see each other face-to-face, I would say a Skype/Facetime call, or a really long two-hour phone call is the equivalent to an in-person visit. )


Step Seven: Don’t Ask What You Can Do- Just Do Something.

When you ask “What Can I Do?” it puts the responsibility back on your friend, and not on you to actually do the nice thing. So just do something nice. Without asking.

Step Seven: Don't Ask What You Can Do. Just Do Something

It's human nature to ask, "What can I do to help?" when you see someone suffering. But the thing is, for the suffering person, that's another thing on their to-do list: oh great, now I have to think of what I would want done, and tell someone else what they can do and when they could do it for me to make me feel better? No thanks, is what they are thinking. When you ask "What can I do?" it takes the responsibility off your shoulders, the giver, and places it back on theirs. Not cool. Also, a lot of times, people who are going through a tough time at work can't even articulate what it is you could do for them. The fact is, when you are struggling, you don't know what would help, other than people just being nice to you.

So don't ask what you can do. Just do the damn thing something instead. Make a list of things you think you could do that would be nice, and then just do it. The best kinds of gifts are the ones that show up un-asked for and un-announced. Take them out to dinner, drop off a pie, send them a gift you know they would love, or think of something you could do that would take the weight off their shoulders. One of the nicest things my boyfriend did for me when I was looking for a job was to show up one day with a Starbucks gift card so I could take people out for coffee meetings or spend all weekend at the coffeeshop working on my resume without dipping into my funds. Simple, personalized, sweet, and un-asked for. Those are the best kinds of gifts, and they truly do make a difference.

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Step Eight: Share Your Own Challenges to Even Out the Vulnerability Dynamics.

Your friend is going to be baring their soul to you, but they don’t want to feel alone in their own work challenges. Share your own stories of how you have (or are trying to) overcome challenges at work to inspire them and build trust.

Step Eight: Share Your Own Challenges As Well As What You Are Doing to Combat Them in Order to Succeed

Another great way to support your friend is to talk about current challenges you are facing. People who need emotional support are often in the awkward spot of wanting to share how they feel or what they are struggling with, but they also don't want to feel like they are the only ones who are struggling. Make your friend feel less alone by talking about something different yet similar that you yourself are going through. A key part of building intimate relationships is that both parties are able to be equally vulnerable with each other. By this point in your support journey, your friend has probably bared their sole to you about the things they are struggling with when it comes to work. Even out the vulnerability dynamics by sharing something equally distressing for yourself. This works best if you are both relatively close to each other, and if you have something appropriate to share. By talking candidly in this way, you build trust and intimacy, while also making your friend feel less alone in their troubles. You've heard of the phrase 'Misery loves company' right? Sometimes all someone else who is struggling wants to hear is that someone else is struggling too. It's like a soothing balm for their wounded souls. And finally, by sharing with your friend the ways you are trying to solve your own problems, you give them a little bit of inspiration in how they could look at solving their own. You might find that through this process you both benefit. Outward accountability, and talking about our goals and dreams with others is a sure-fire way to work towards them with more focus and passion. You might get a lot more out of this process than you bargained for!

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Step Nine: Rinse, Repeat, and Refer.

Share the power of your network and refer your friend to the people, places, and things that can help them find their next groove in life. And if you think they need more support than you alone can offer - refer them to a trained professional or counselor who can also be a support.

Step Nine: Rinse, Repeat, and Refer

We've covered a lot of steps so far. I promised I would write in broad strokes and keep this simple, so I only have two more tips about helping others in work transitions. In addition to all of the above, one of my final tips is this: rinse, repeat, and refer.

Keep listening, keep talking, keep checking in, keep doing nice things, keep complimenting, and keep talking about your own challenges. And then refer, refer, refer. Recommend that your friend meet with people in your network to get ideas about work and future opportunities, so long as these meetings are mutually beneficial to all parties. Refer them to books, movies, podcasts, resources, job listings as you come across that they might find useful or inspirational. Refer them to the people, places, and things that you think they would like or learn from. This is the part where LinkedIn can really come in handy and be a helpful tool during the transition process. Introduce your friend via InMail to some of your connections, comment on posts and @mention your friend if they would also find the content helpful and appropriate, copy links to jobs posted on LinkedIn, and send the opportunity to them over private email, the list goes on. Give them a recommendation on their LinkedIn profile, and vouch for them on certain skills that they know they have in spades. Our networks are incredibly powerful things that introduce people to hidden opportunities, so make sure that you use yours to benefit others - and not just yourself - too. Outside of LinkedIn, you can share interesting developments, trends, articles, or events that they would enjoy learning from, and share any resources that have helped you in the past. There is no limit to what we can share with others.

The final part of the referral step here is also to recognize when your assistance might not be enough. There is only so much support one friend can give, and if you feel that your friend needs more emotional support than you have time or training to offer, always refer them to trained counselors, therapists, support groups, healers, or spiritual leaders who can give them the further counsel they may need during their work transition journey. Again, this is sensitive and complicated territory, so I will leave how to do this part of the process for a different post where we can really focus on how to steer those you love to support groups and counseling.


Step Ten: Do Fun Things With Your Friend

Take your friend’s mind off of things by planning fun get-togethers and making sure to not talk about work while you do them!

Step Ten: Do Fun Things with Your Friend Outside of Work. Tip: These Outings Should Have Nothing to Do with Work! (Use the illustration above as inspiration.)

Finally, and most importantly: make time to do fun things with your friend outside of work that have nothing to do with work. I firmly believe that the key to happy and meaningful life fueled with purpose is to have strong friendships, hobbies, and passions that exist far outside of your title or industry. I'm not saying everyone should feel like this at all, but it is a strategy that so far has held up and proven to work for me. Personally, I find that I am most grateful for my outside passions, interests, and times with friends and family when work times are a little tougher - another good reason to pursue your hobbies and keep your connections strong. Think of it like having bad-job insurance!

Having things to look forward to outside of the M-F has a huge boost on our mood and overall happiness. Not to mention they are just plain fun! So help take your friend's mind off of things by making plans to see a movie, go on a walk, craft together, or just drink wine and watch the Bachelorette and dance around the living room to Miranda Lambert. It doesn't have to be complicated or a big to-do, (in fact, it shouldn't, because a friend who is kind of down is not going to be all into planning major brunches mode), so just show up, bring a glass of wine and a listening ear, and try to have a little bit of fun.

If we didn't have the winter we wouldn't be so aware of the beauty and relief of spring. So lean into the suck of how work can be hard sometimes and be there for your friend while they move through this chapter and figure out what's next. All things change, and so I hope that in time if you have a friend who is struggling with things at work, that they find new opportunities and solutions that make their heart happy again.

Deep peace,


// Image Credits: Illustrations from the 'Taste Buds' Series by Phillip Tseng, a Designer and Illustrator in living and working in San Diego, California. Find more of his work here: