Back in the day Perfect Manifesto was used more as a place I would use to document and keep accountable on a wide range of goals.

One of those big ambitions was to improve my assertiveness, this article I wrote way back when – How not to be a pushover discusses this problem.

As I look over this post, I want to revisit the subject matter, discussing my assertiveness journey and the improvements made over the last four years.

So let’s begin…

The year is 2017…

A time when Britain triggered proceedings to leave the European Union, actor Warren Beatty got crucified for announcing the wrong winner at the Oscars, and you could go out in public without being judged.

For me it was a monumental year – I started a new high-pressured job, content with the knowledge that towards the end of the year I would get to experience the joy of becoming a father.

With my life taking so many positive steps forward, there was more demand on my time, so in reflection I can understand why becoming more assertive became more important, so that these pressures didn’t get on top of me.

Or as I kept eloquently saying – to not be a pushover.

Now let’s summarise what my original problems were:

  • I take on too much responsibility because I can’t say no.
  • In my attempts to impress, I come off as being unable to make tough decisions, trying to make everyone happy.
  • People know I am a pushover and take advantage.
  • I encounter situations I am not happy about, but don’t do anything about it.
  • Friends and family make bad decisions because I am scared to offend.
Self-confidence? Image from Pixabay

If you’ve had issues with your own assertiveness, some of these may seem similar.  The first step to addressing these issues was accepting that I was a pushover, a noble approach to be honest and accountable.

This was followed by a few tasks to establish how to be more assertive:

  1. Have assertive role models
  2. Read literature on assertiveness
  3. Create assertive rules
  4. Make an assertive decision everyday

What I was trying to do was follow a SMART approach, by writing these ideas down as a ‘to do list’ turned an objective that was woolly and quite difficult to measure into something I could work towards.

Of the four the biggest game change was:

Make an assertive decision everyday

To Powerhouse…

Assertive literature has it’s uses in understanding the theory behind making a decision.  It enables you to understand how you can respond when you are put in a difficult situation.

But it is worthless without practice.

With assertiveness, you also need to reach that breaking point where you know you can’t take anymore, when you think to yourself “No more Mr. Nice Guy, I’m going to focus on my own self-interests”.

That moment came when a colleague thought they were making a complement about me:

“I like James, he’ll do anything you ask”

This actually offended me – did they like me because I was a genuinely good person whose company they enjoyed?  Or was it because I did whatever they asked?

This was the turning point in my assertiveness, when people came to me with all their tasks I started pushing back – I would question what the urgency and need was, say I had other priorities and sometimes outright say ‘No’.

How did that impact my relationships?

Well I noticed some people I thought I was friends with, weren’t quite as friendly, I stopped getting people asking me about things every day and getting me to pass on all their donkey work.

But what I did feel was a lot more respect in my experience and knowledge.  This led me to go work in another team, where I was able to lead and influence how the space was ran.

A good book to help you understand influence, persuasion and negotiation…

The best book in my assertiveness journey is Never Split the Difference by Chris Voss, a former FBI hostage negotiator.

The book was written with a salesperson in mind, but I’ve found the techniques really educational to help with my confidence when dealing with others.

I intend to discuss some of the lessons in further detail in a future post, but I will direct you to the “How am I supposed to do that?…” approach, something I have found really useful for managing demands on my time.

When pushed to do something, I attempt to make my requestor have to work hard to give me the unwanted task, by pushing back with a question:

“I have X and Y still to do, how am I supposed to do that?…”


My assertiveness journey is far from over.  You’ll have to excuse the artistic license applied on this post, but I would say I am nowhere near being a “Powerhouse.”

As was set in my objectives all those years ago, to keep getting better you need to make an assertive decision every day.

This means challenging the very nature of the world that surrounds you.

Good luck!

Thanks for reading, what things do you do to assert yourself – at work and home?

James @Perfect Manifesto.


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8 thoughts on “From Pushover to Powerhouse: How To Be More Assertive

  1. Sounds like this is going well for you James. I wouldn’t say I was a pushover but i do struggle saying no, I just want to help and please people even if it means taking on more than I can handle.

    Liked by 1 person

    1. Thanks for the comment. Saying no is something I’ve found outright saying ‘no’ to people difficult, though have found during my response into questions helpful, as if I’m too busy they’ll either take that into consideration, or change their mind.


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