On Fear, Courage & Making The Ask

Fear of negotiating

Every one is scared of something. And what’s nerve wracking for some may be a piece of cake for others. (Like public speaking. Apparently it’s one of the most common fears…but I LOVE it.)

My biggest non-business fear is snakes. Growing up, kids would taunt me by getting books from the library with snake pictures and surprising me with them. Eeeeeps! Even years later, despite what I suppose amounts to brief exposure therapy during the grade school reptile show, I’m petrified. 

But it’s no big deal. I live in a big city, don’t vacation in exotic locations, and as long as I keep my wits (and map) about me while visiting zoos, the chances of me needing to confront this fear are minimal.

The same can’t be said for business related fears.

I’m willing to hazard a guess that not far behind public speaking on a work-related list of fears is asking for things…a.k.a. negotiating.  And sure, it’s possible to avoid it all-together, even as an entrepreneur…as long as you’re ok with ‘meh’ results and quite literally just taking what you can get, instead of what you need/want/deserve.

But if you’re like me, you want business to grow. You want to sign new clients, work with the best service providers, and still have time and energy left at the end of the day. So – let’s put on our big guy/gal boots, and figure out how to shake off this fear.

How to overcome fear of ‘the ask’

Here are my 3 go-to strategies for getting rid of the resistance and getting my butt into gear.

Ask yourself: “What happens if I don’t ask? Where will I be 1 year from now if I don’t ask?”

At some point, if you’re thinking of asking for something that scares you, there will be the temptation to rationalize it away. Maybe you don’t reeeealllly need it? Maybe things won’t be thaaaat bad without it? The benefit of asking can’t possibly outweigh the panic/pain of asking…can it?

These could all be valid – but make sure that you’re not really just wimping out by considering what life will be like if the status quo stays. Will you be fulfilled sitting exactly where you are a year from now? What if your same-month business results next year are flat?

If you’re less than thrilled at that thought – buck up. Time to ask.

Get real about it: “What’s the worst that can happen?”

Oh! The possibilities! Of the top of my head: the sky could crash down, a giant wave could come up from behind and sweep you away, you could spontaneously combust, there could be laughing/pointing/mocking…or – and stick with me on this – they could say no.


One tiny word, two teensy letters. And that’s probably the worst it will be.

We’ve heard ‘no’ lots of times before in our lives and have survived.

If you’re still worried, get some practice by asking for little things – unrelated to your business perhaps – that aren’t too risky. Quick! Think of something that you can practice with today- and take action.

Plan to succeed: Put your best foot forward – prepare.

Here we go! You know that moving through your fear and making the ask will be a good thing – it’ll move your business farther ahead. And you know that the world won’t end if you ask…the worst that can happen it probably a no. If you need to shore up your courage further, know that how you ask for something can increase your chances of success.

Key here is taking your time. The bigger the ask, the longer you can spend on preparation. Figure out exactly what you need, identify the right client, vendor or contact to ask, and then make sure that the way you’re asking aligns with how they’ll be most receptive and open to giving that ‘yes!’.

So – what are you scared of right now? How important is it for you to shake off that status quo? What are you going to do tomorrow to start breaking down that fear of getting a ‘no’?