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The Friend Zone: Not Just a Problem for Dudebros.

Phil Bennett Posted by Phil Bennett in Uncategorized 7 min read

Getting ‘Friend Zoned’ is a fear of all douchebag alpha male dudebros. But, as a manager how do you balance being a friend with being a colleague?

The thing that I’m worst at is working how close I should get to my colleagues. How much I should let them into the world of Phil. Should I become friends with them? Or simply treat them as people I work with?

I have got this VERY wrong in the past. So for come context let me tell you three stories.

Story 1: Business Partners For Life.

After a long period of freelancing, I started working with a talented designer. I would step in and build out his project when he needed a developer, and he would provide me with design support when a client needed something more than development work from me.

After a period of sending each other invoices that generally ended up cancelling each other out, we sat down and decided on starting our own Web Design and Development agency. With our combined skills, we could conquer the world.

We were very wrong. Our confidence in our own skills was valid, we built some fantastic projects in this period. He was a great designer, I was a great developer. However, we both colossally sucked at running a business. It’s bloody hard, and we had no idea what we were doing.

Failing Hard.

We didn’t understand the importance of cash flow and that fundamental failure crippled the business. We ended up bouncing from invoice to invoice to pay our costs.

Before starting the business, and while running it, we became excellent friends. This person was loyal, kind and fun. All the thing you want in a friend.

As things got worse and more personally and financially painful, it was evident that he wanted to push through every challenge with dog-headed determination. But I wanted out, I couldn’t take it anymore.

But I knew that walking away from the project would completely fuck him over and I couldn’t do that to a Friend. So I persisted and worked my buttocks off to try and push through the problems.

And I burnt out. Badly. I was so stressed I couldn’t sleep without a drink. My bank account was empty I was so financially broken that I couldn’t really afford any food that wasn’t beige; noddles, bread, and cheap cheese.

I got sick, and I just couldn’t continue. Eventually, I had no other option but to walk away and get a fulltime job. The time that I broke the news to my business partner is still burnt into my memory. It was heartbreaking.

But I should have done it months earlier, for everyone’s sake. But I couldn’t, I couldn’t put priorities above that of my friend.

They say never go into business with Friends or Family. I now know why.

Story 2: It’s a family affair.

The company I joined after my business failure was a family run business, run by a fascinatingly talented mother and son duo. I loved working here, I learnt so much. One of the best (and possibly worse) things about the company was its culture.

The owners of the company were incredibly passionate about their company, to the extent it really did feel like a family, not just a family business. This generated significant loyalty from employees while also creating a lot of unnecessary stress.

But the passion showed by my direct lead (the son) was truly inspiring, and I genuinely felt a little bit like a member of the family, maybe a distant cousin. I would, without hesitation, classify this person as a friend.

Life Changes.

Something else happened while I was working at this company, I met the love of my life, my current partner, and soon to be wife!

Then a few months later she had to move to Berlin, this is where the trouble started. She asked me to move to Berlin with her. Even though I was 100% sure that it would be the right idea, my loyalty to the company stopped me from making that decision immediately. I delayed handing in my notice for a few months because I couldn’t deal with the anxiety and stress of going through that process.

With a 3 month notice period added to my dithering, it meant I wouldn’t move to Berlin for 6 months. At this point, I had known my partner for about the same amount of time, 50% of the first year of a relationship being long distance was painful, and I almost lost her in the process.

We made it through, and I’m delighted that it eventually worked out, but once again, I had put someone else before myself and very nearly lost everything in the process.

Story 3: Cold, Clinical, Alone.

It turns out moving to Berlin was a fantastic idea. I’m so much happier here than I have been at any point in my life. I have no idea exactly why but it’s a combination of people, city, and work. All this together that blends to create a lot of awesomeness.

When I moved, I had initially been freelancing. However, after moving to a new city working on your own is a really lonely experience. I decided it was time to get back to ‘proper’ work, for a little security and some people to talk to.

I joined a great development company. But this time I thought ‘twice bitten, thrice shy’ and I kept a regulated emotional distance from my colleagues. I made a promise to myself that I would never again become a friend to my colleagues. Protecting my self, but at the same time being able to be more disciplined in my approach to team management, focusing less on not upsetting or hurting my friends and more on the task at hand.


Sounds horrible, doesn’t it? It was, it took me so much longer to integrate with my team, gaining respect was incredibly hard. However great I did at managing our deliveries without the team actually liking me it was so much harder for them to see the good in what I was doing.

A number of the team were resentful that I had been placed in a management role above them. “Who the fuck is this telling us what to do”. I isolated myself within the company, didn’t have allies, and I didn’t have friends to protect me from all the crappy things that happen day to day in the workplace. This made me miserable and stressed.

The only thing I had was the knowledge that I could get stuff delivered, which lead to me doing a lot of things myself that I should have been letting the team do. I picked up a lot more work than I really should and worked too many hours producing stuff fast, but not at a quality level anyone was happy about.

I eventually let this guard down and acted in my more rational, human, fashion. Things got a lot better from there on in, and I managed to develop a well-performing team with a culture of trust and respect. But I still really regret telling members of the group the above stories and informing then that I could never see them as friends, only colleagues. Yeah… I actually said that.

Hopefully, now, after I’ve left this company, I can repair this damage. I still see some of the team and have no other reason other than friendship, thinly disguised as mentorship.


So, how do you balance the benefits of close personal relationships? How do you make sure you’re not fucking yourself and putting other people before yourself?

I’m still not 100% sure if I have got this right, I think it’s probably my most significant opportunity area for self-improvement. However, I’ve started to allow myself to classify my work colleagues as friends, but now I follow a few rules that will enable me to know when to put myself first and when to put the team first.

  • Keep a clean boundary between personal life and work life, don’t let too much of one seep into the other. For example, don’t work from home unless you have to, but if you need to make sure you have a precisely defined area for doing so.
  • When making tough personal choices, how your colleagues feel should never be part of the decision process.
  • Do socialize with your teammates, work is better when everyone gets along, and it’s ok to bond and become friends.
  • Share some things, Keep something secret. Show that you’re human and exist outside of work, but keep somethings private, so you have places and experiences to go that are 100% work free.
  • Try to understand other people’s emotional needs in this area. Don’t cut people off that want to be your friend, they will only feel snubbed. But additionally, don’t try and drag that one teammate out to every social event when it’s evident aren’t interested.
  • I think the most crucial part is making a clear distinction between work decisions and life decisions. You should never make life decisions influenced by work emotions.