cover art of Changes Big and small episode titled Overcoming the Challenges of Making Friends at Work

You would be disappointed if the person says no, but you would also be disappointed if you didn’t ask. So it’s what side of disappointment would you want to be as far as friendships or any relationship?

Best friends at work

Both @shikachica and I have had best friends at work. In Shika’s case, she was roommates with a best friend from work. In my case, I lived across the hall from a best friend at work and we shared a car. Best friends at work may not be the only best friend, but based on proximity, time together, common interests, etc., you can build a very close, strong friendship with someone from work. However, in both our cases, when we didn’t see the person as much, those friendships waned; we’re still friends with those former work best friends but the relationship is not as close.

In my case, I’ve worked in Canada, India, Sudan, Japan, and the Czech Republic. As I moved from country to country, I often joined a new school together with some other newbies. We would all be hungry for friends in our new environment, and that was an excellent breeding ground for forging strong, close friendships.

Maintaining Relationships 

It is much easier to maintain relationships at a distance now than it was in the past considering all the new tools that we have for remote communication. However, it takes more intention and deliberate practice. When we plan to meet online, it’s much easier to put off a meeting, to delay it, to get caught up in work, and think we can reschedule social calls. Even though it is easier to stay in touch than before in terms of tools, it can be hard to interrupt our work pattern, to put away our work for a while to socialize with a work friend. The barrier to rescheduling is much lower for in-person meetings and so that makes it even harder to create and maintain close relationships.

What’s required here is a mindset shift. Why don’t we treat online social calls like we do in-person meetings? I know for myself, I feel guilty for taking time to meet people at work when I could be “working”. This is despite my knowledge of how important social relationships are at work. I’ve read the research about the improvements in engagement and in mental health. Yet, I don’t feel completely comfortable taking work time to socialize, and when I do that, I tend to clock additional time at work to make up the time lost in socializing. :grimacing??

Career Friendships Remotely and as a Solopreneur

If you are a solopreneur or work remotely, it can take more effort to create friends at work. One of the ways that we deepen friendships is by spending time together. Being in the same place makes it easier to create a friendship. So what can we do when we work remotely or when we work alone?

While I have created some friendships at work, it is with people that I have met face-to-face on a meetup where we were able to see each other, where we were able to spend time with each other. And it’s difficult to maintain those relationships. We don’t come across each other spontaneously. We have to get into each other’s calendars. We’ve got to schedule a Zoom call or some sort of occasion for us to chat. And then we have to commit to that chat and avoid any feelings of guilt.

A Strategy for Connecting with Friends in Person

Shika mentioned a new technique that that’s she’s been using, to not rely on Zoom if meeting someone I know in her city. Instead, she finds an activity that they both enjoy and schedules to do that activity together. This adds excitement and accountability since she is doing something that she wants and enjoys doing while also meeting with a friend. In those cases, Zoom is a backup method for a meeting rather than the main one. When friends are not in the same town, it’s more complicated, especially when you have to contend with time differences.

 As a self-employed person, Shika makes friends either at networking events or through training for certifications. She manages to talk to some of those friends each week, which helps with the loneliness of being an entrepreneur. While many people focus on the freedom of being an entrepreneur, it’s also lonely. This makes it important to manage your mental health, and that means finding ways to connect and socialize with others. Shika finds it important to have someone that can hold space for her. Through community events, she’s been able to meet people with common interests. However, she has had to go outside of her comfort zone to find friendships. You don’t have to find someone who’s also an entrepreneur but it has to be someone that you can talk to.

Professional/Career Connections outside of Work

When I first joined Twitter, I used to regularly join conversations, education streams around particular topics. In that way, I built some light friendships, people who I would watch out for their responses, who I would reply to and who would reply to me. When I went to a conference, I would look for them and say hello. As I moved away from education and decreased my participation in social media, those relationships disappeared.

 I think professional conferences, professional networking events, we can still kind of consider that making friends at work. Maybe the person is not in your same company or in the same space as you, but those still count as career friendships and can be really helpful for providing that support, for helping you stay engaged, for helping you work through things that you’re thinking about, providing perspective, all of those things that friends at work do. For example, just last week I struck up a conversation with a professional friend. We were both teachers in Japan even though we were not teaching at the same school. We’ve met each other at many conferences, and she has been on the podcast. I shared something with her on Instagram and she communicated back and now we’ve planned a Zoom meeting together. She shared that it’s really nice to talk with somebody who is thinking about some of the same things that she’s thinking about and so we scheduled a chat.

I think that it’s helpful to have people who can relate to some of the things that you are going through, who are interested in some of the same topics and some of the same conversation. It’s a very different conversation when you have engagement and excitement from somebody on a similar journey to you and somebody interested in your journey as opposed to somebody who’s trying to be a good friend but is not so keen on whatever you’re talking about. 

Simplifying Professional Friendships

 The biggest way of finding a friendship is focusing on what support do you desire at the end of the day for a relationship. A lot of people focus so much on what they don’t have. We’ve discussed many of the challenges of creating friendships in this episode. But no one talks about focusing on what you personally desire and can change.

When you’re thinking about making friends, your desire could be talking about a specific hardship you’re going through. In that relationship, the purpose and the lesson there is to help you through that. What if we allowed ourselves a lighter approach to friendship. We’d be able to trust people more through this new medium that we’re going through right now, whether that’s meeting people at work or meeting someone through training or a conference. Work friends may come and go. Some of them may be there to support you while you’re going through transition or. you might support them in that way. We can be grateful for those relationships. They have value even if they have a more constrained duration.

In a previous episode, I talked to Ellen and Jeff White, who talked about doing an audit of the people that you spend time with. We all have limited time so we have to decide who we’re going to spend additional time with. And so if you’ve got friends at work, from college, from the gym and other areas of life, they’re not all going to take the same amount of time. After all, we have a limited amount of time. You’re going to have to decide who are the people we only meet in particular places, for example, at work, and who do we meet during our “free” time. My work friends, even though they’re really good friends and we support each other, maybe that happens during the week. And maybe the people in my city, that happens on the weekend. 


My invitation to you is for you to do an audit of the friendships that you’ve made over your career, at work. Are those satisfactory for you? Do you need to change something about them? And if you are missing having a friend at work, do an exploration, do a test to see how could you create some of those connections. Is there somebody that seems amenable to being a friend that you could reach out to more regularly for a DM? Are there people that you could reach out to have a more open and general chat with every once in a while? Could you explore and see who might be open to the kind of friendship, who else is looking for that kind of friendship that you want? Are you comfortable telling someone that you want to be their friend or do you want to explore friendship with more subtlety?

Using Appreciation to Build Friendship

Shika shared an approach that has helped her. She uses appreciation to let people know that she appreciated their time together. Some phrases that she might use individually or in combination include:

  • I appreciate our time together.
  • Thank you so much for having the Zoom call with me.
  • Thank you so much for going for a walk with me.
  • I really needed that.
  • There’s just so much stuff that you said that just really resonated with me. 

Appreciation is a great way of creating that step of letting the person know that you do see them as a friend. When you feel comfortable, you can then say “I’m so grateful to have a friend like you”. This approach is a great way of building vulnerability when you start a friendship at work or at an event, building that appreciation for someone and vocalizing it.

Inviting Friendship

 If you are interested in building a friendship with someone at work, invite the person to meet, to talk, to schedule something regularly, and see how they respond. You don’t have to be pushy, but you have to at least let your interest be known in establishing some sort of regular opportunity to connect and to create some bonds. 

 Shika shared her approach:

When I do a Zoom call with someone and it’s like our first time chatting, I’m like, you know, I really had fun doing this. Are you available in the future for us to do another Zoom call? And then this is kind of the point when you can tune in and see are they actually interested in chatting or not?

This shows an approach to letting your interest in friendship be known. It’s almost like on a date, essentially. It’s the same approach as checking if someone is interested in a second date.

Try not to put a lot of pressure and build disappointment. You would be disappointed if the person says no, but you would also be disappointed if you didn’t ask. So it’s what side of disappointment would you want to be as far as friendships or any relationship? That way can allow you to be more in the flow of the experience. You don’t have to tie your worth to the other person’s response.

Don’t be fearful of disappointment and rejection and just know that it’s an opportunity. Don’t be so afraid of making new friendships when you do your audits. Consider who is in alignment of continuing and growing with you. 

 I did a survey on Instagram to ask people how close to a best friend they think that their closest friend at work is. The response didn’t surprise me. Maybe it is a generational thing, I’m not sure, but I do think it’s true that most people do not have a best friend at work, even though Gallup says that this is a great indicator of people’s engagement in work. 

Have Fun with Friendships

My takeaway from my conversation with Shika today, and something that I’m going to do, is to play around with approaches to building friends at work and have fun with it. If you had a great conversation with somebody, then as Shika shared, you could say “I really enjoyed our chat. I’m available on Thursdays. If you want to do this again, send me an invite. I’d love to.” It could be as low-key as that, where you could be really open and non-pushy, to “I’d love to meet you again next Thursday. Are you available then?”, where you put the person right on the spot. 

It depends on what’s your character, how you like to show up and relate in the world. So you can decide what works for you and play around with it. I think a lot of people are looking for connections. It’s unlikely to just be you who is feeling that way. So what you have to do is find your people, and you’re not going to do that unless you put yourself out there. Oh my goodness. It really does sound like dating advice. 

 Shika noted that the more you strengthen your friendships, really making sure you have really intentional friendships, then the more that you’ll be able to find that intention in your current and future intimate relationship. Making a friend at work doesn’t have to be a high-pressure activity. Explore what works and what feels good. Try to be clear in your communication and make your interest clear. Follow through on any meetings that you set up and match your actions to your interest and intention.

Connect with Us

You can connect with Shika on Instagram and with Damianne on the Changes BIG and small website, Facebook, Instagram, Twitter, YouTube. You’re also invited to join the Changes BIG and small Facebook community.

Listen now


[03:14] Maintaining Relationships 
[06:17] Career Friendships Remotely and as a Solopreneur
[16:05] Simplifying Professional Friendships
[18:49] Invitation/Challenge
[19:52] Using Appreciation to Build Friendship

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1 comment on “Overcoming the Challenges of Making Friends at Work

  1. I agree with every factor that you have pointed out. Thank you for sharing your beautiful thoughts on this. Check this out –> Friends here… There…. Everywhere!!!

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