3 Ways to Negotiate Your Salary When the Odds Are Against You

“I want to make more money, but there’s no use in asking for a raise at my current job. There are too many reasons I’ll get a no,” said Jessica*, a marketing assistant and member of the Work Bigger community.

Jessica’s underpaid in her current role, and she hasn’t asked for more because the following roadblocks are stacked up against her.

  • I’d need to discuss the raise with a top executive, and I’ve never gotten my way when asking for other things in the past with him. He’s extremely difficult and unpleasant.
  • I received a raise recently. And though it’s still way below market, asking for a significant jump feels like a joke.
  • I’m leaving the company soon-ish, so why even try and stir the pot?
  • It’s not the right time because budgets are reviewed at the end of the year.
  • Asking isn’t encouraged in our company culture.
  • I don’t know how to negotiate.

Feel familiar? That moment when we wish for something different but the roadblocks are significant.

How do we tackle this? And should we tackle it?

There’s a 100 percent chance you won’t earn more money if you don’t ask; but if you do ask, your odds are better no matter what.

Read below to learn three ways to negotiate for more money and overcome BIG roadblocks in your work when the odds are against you.

Sort the Challenges: BIG vs. Workable

Not all roadblocks are created equal. Some of the roadblocks on your list may feel extra challenging while others may be easier to solve.

For example, the first issue, having to negotiate with a difficult top executive, may be on your “biggest challenges” list. Negotiating can be nerve-wracking, and it can also be demotivating if you feel there’s no way to bring the other team on your side.

On the contrary, more manageable roadblocks may include challenges that when left to stand on their own, aren’t as overwhelming. With some work, you can find and implement a solution.

Check in with your gut when reviewing your lists. Which roadblocks feel extremely daunting or intimidating?

Then look at the issues on their own – one by one versus in a group. Are there any issues that feel easier to tackle? Where are the low-hanging fruit?

There won’t be a solution for everything, but if you try to find the solution in some things, your perception may shift.

Similarly, be fully aware and keep a pulse on the more challenging roadblocks (e.g. a horrible boss, budget, recently received a raise.) You can think of ways to tackle these in your strategy, and in the case you can’t, you’ll ask anyway having greater awareness of your circumstances.

Develop a Strategy

Preparation is key. Before you make the ask, get clear on the following:


What’s your ideal number? Be honest, and aim high. What would make you really happy? Forget about what’s “realistic” for the moment; instead, focus on what feels great given your experience and the market rate.

Always ask for higher than your target number. For example, if you want to make $65K, ask for $70K or $75K (given you have a strong rationale and data to back up this ask). It’s unlikely you’ll get a YES right away, so you need to create a buffer to get as close as possible to your target number.

Your Bottom Line

What’s the lowest you’re willing to accept? In Jessica’s case, it may be her current salary. She may get a straight no and not have other options lined up, in which case she’d have to accept the offer (see Plan B below). Either way, get clear on your boundaries, and don’t share your bottom line with anyone.


Why are you asking for this raise? What have you done to earn it? This is where you should spend a lot of time preparing your story and using any data to drive your point home. To make this even stronger, go back to the reasons you’ll get a no. What’s your comeback for each challenge? 

For example, if you recently received a raise, and the jump to your target number is so much higher, how can you provide proof that you’re worth the significant jump? If the timing isn’t right because of budget planning, when is the right time? And what can you do in the meantime so that once budget planning hits, your raise is baked into that new budget.

Prepare to tackle any objections through questioning and collaboration. Here’s a thorough step-by-step negotiation strategy guide – our “How to Negotiate without Losing Friends, Fans or Job Offers” framework –  to help you prepare for the conversation. CLICK HERE to download.

Work on Plan B

If you’re a long-time reader of this site, then you know the workplace is changing. Having a side hustle is typical. So if your company isn’t giving you that raise, and you’re not feeling valued, what’s your plan B?

Are you looking to find a new 9 to 5, or are you working on a side hustle. If this 9 to 5 isn’t forever because you’re going to be an entrepreneur someday, start working on that now. What do you need to do to get your business moving?

There isn’t only one way to bring in an income (e.g. your boss saying YES to your raise). There are several side-hustle options today that can (1) offer you the opportunity to gain a new skill-set so you can more confidently advocate for more money at work, (2) lead you to a better job or (3) lead you to running your own business.

The goal is to  consistently increase your revenue, whether your 9 to 5 says yes or no to your ask. Set yourself up for success sooner than later, and never put a hold on your earnings.

In Conclusion: Make More Money Even When the Odds Are Against You

“The only way I was going to determine my own future was to do it myself.”– Ina Garten on starting her own business.

We’re not in control of everything, but we do have some control in how we respond to roadblocks and problems. There’s a solution for everything. We just have to look for it. Download your full negotiation strategy guide here so you’re fully prepared to make the ask.

Then tell us in the comments, what’s the greatest insight you’ve taken from this article? And, what’s one thing you can do to increase your chances of getting a YES during your next negotiation?

*name has been changed