Saying Yes and No with Confidence: Unveiling the Tipping Point in Our Careers

Experts on social media often lecture women on setting boundaries in the workplace. We hear it from our therapists, our partners, our friends. We should say “no” more often, but the advice never comes with a script or playbook for how or when to say no. On the opposite end of the advice spectrum, we hear from a seemingly equal amount of experts that we should always say “yes” (or at least that we’ll be more interesting if we do); to new experiences, job responsibilities, and events. They tell us to network relentlessly, saying “yes” to small talk and after-work hours. They tell us that if we don’t say “yes,” we ruin our career prospects.

So, which is it? Do we say “yes,” “no,” or some mix? Knowing when to say “yes” or “no” is one of the most important distinctions women can make central to their career success.

The All or Nothing Mentality

My first post-college job laid me off. That is not exactly how a graduate with copious student loans wants to start a career. I was stuck, lost, and looking for direction. Rejections came flooding into my inbox, but I also did a fair amount of rejection. 

During this time, a time I would later speak about in a TEDx Talk, I came across the movie “Yes Man.” In the film, a man who says “no” to new things has his life changed by starting to say “yes” to every experience. As you can imagine, hilarity and some bad luck ensue. However, he also finds his dream partner and job. This is an example of the all-or-nothing mentality, but it spoke to me instantly, and I decided to do something similar with my life.

yes woman

Saying Yes to Everything

Let’s look at my circumstances at that time: no mortgage, no spouse, no children, no job, no direction. At that point, saying “yes” would benefit me far more than saying “no.” In the next two years, I worked on a landscaping and masonry crew, as a Capitol Hill intern, in a tutoring center, as an NFL analyst, and as a wealth management researcher. I said “yes” to everything. 

The wealth management job led me to financial analysis at DoD firms. NFL work introduced me to incredible people and opportunities. It also led me to more yeses, like attending Boston University to start my Master’s in Computer Science (even though I had no CS background). I won hackathons and awards. I tried everything and entered every contest. I wanted to make some sort of life for myself.

Burned Out With No Boundaries in the Workplace

At some point along the way, work overtook my life. My son was born, and I spent more time away from him than with him. The drive to never be a “failure” again overtook my life. 

I spoke at every event and took on work far beyond my job descriptions (with zero rewards in some instances). It should have been no surprise when I burned out. My anxiety was through the roof. I didn’t know what made me happy anymore. 

But I had an emergency fund for the first time in my life! I could relax, right? Now I had the spouse, mortgage, and child. Much more responsibility, so I thought I still needed to say yes to everything to avoid losing it all. I said yes to an Executive MBA program and justified it with “just in case I get laid off.” I was acting from a place of scarcity, but there was no scarcity anymore. I needed to build boundaries but kept thinking, “What IF.”

The Privilege of Setting Boundaries in the Workplace

That was my tipping point. Being financially secure is a privilege, and it has afforded me the ability to say no. But some of us can’t afford to say no right now. And that does not make us any less badass. But the career/life goal is to get to a place where we CAN say no. That’s better than any title. That’s freedom. Whether we can say no to working for someone else, no to late hours, or no to 100-hour weeks, we can quit jobs when it becomes toxic. Single moms can’t say no. BIPOC women often can’t say no. It’s a privilege to be able to say no.

saying no at work

Learning How to Say No

How do you do it when you get to a place where you CAN say no? I began treating asks like I was a company. What’s the ROI? And not just in terms of money but value brought to my life. Did taking on X provide more value than I spent in labor? Was that value tangible or intangible? Did saying yes mean I was compensated with PR, job offers, consulting offers, or something else? 

I’m incentivized to say yes at work with a paycheck and health insurance, but am I saying yes to promotable work and no to work that I can delegate or automate? I worked at a job where I was constantly the ‘notes girl.’ I never got promoted, even though they told me my note-taking was helpful for the teams. I could never get out of that label. If someone asks you to take notes, remember that’s not promotable work and send them a link to an AI note-taking app. Tell them that you will be focusing on value-add work.
If you’ve been conditioned to say yes, either by others or yourself, it’s a tough habit to break. The temptation to respond immediately to Slack messages and jump on requests is strong. Carve time out in your day to respond to people, and let them know up-front that you respond to messages at set times, say 11 a.m. and 4 p.m.

The Concept of “Yes, And…”

Practice the concept of “Yes, and…” It’s a tactic rooted in improv that has great implications for prioritization and time management. 

For example, A big boss comes to you and asks if you can deliver an airplane in two weeks. You internally freak out. There’s no way! Hit them with the “Yes, and… I will make it out of paper clips.” Or, a more serious answer “Yes, and it will be a blueprint, and I’ll need to shelf the hovercraft project. Shall I get started?” That way, you aren’t jumping right into saying, “No, you’re insane.” You’re telling them that you’d love to help them, but there are conditions, and you’re forcing them to do the prioritization exercise. 

The Importance of Prioritization

I like to keep a kanban-style board for my and my team’s tasks. We prioritize them each week. If an urgent ask comes in from above that throws off our schedule, I show the asker the board and ask them to work with the owners of the other initiatives to figure out which one should drop to accommodate. Nine times out of 10, it turns out that their request is not so urgent, and we put it on the calendar for later in the month. If it is urgent, they must own it, and the slippage on the now de-prioritized item. Our workload has stayed pretty much the same, but we look great because we ‘technically’ said yes.

There are other times when you just have to say no. A plain, flat-out no. This doesn’t mean being rude and just saying no and walking away. I often get invited to after-work events, and sometimes they don’t work for my schedule. “I can’t make it this time due to childcare, but if you schedule future events during working hours, I’d be happy to attend!”

own your time

Own Your Time

Owning my time is extremely important to me. It is MY time. MY time with my family, MY time with myself, MY time to breathe, read, drink wine, or whatever else it is that sets my soul on fire. It’s finite. It’s going to end someday. And I want to be PRESENT for all of it. The skinned knees, grass-stained clothes, and chocolate hands, running through the sprinkler. The joy of life tends to fade if we let others manage our time by acquiescing to every little request to please everyone else. The people who truly love you will be happy when you are PRESENT.


Life (and the internet) are filled with self-proclaimed gurus who will give you contradictory advice about nearly everything. They’re trying to sell themselves with bold talking points, but the truth is, there’s no one-size-fits-all approach, especially when it comes to saying “yes” or “no.”

Seek out mentors who have walked a mile in similar shoes, and remember that most of the folks giving advice can only speak from their own lived experience. You’re bound to get whiplash if you follow every self-proclaimed ‘expert’ online, so curate your feed to align with your situation and values. In the end, the most important “yes” will be the one you give yourself to be true to your values and dreams.


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Jess Sahagian

Jess Sahagian

CTO & Co-Founder of Appraisely

Jess leads the Engineering Program Management team at WHOOP, a Boston-based health and wellness company. She is also the Co-Founder and CTO of real estate startup Appraisely, a recent Executive MBA graduate, and a Mom to an active, mischievous, and joyful toddler. With a passion for the space where tech meets humanity, Jess has built her career and life on a foundation of psychological safety and being an unapologetic hypewoman for her colleagues, family, and friends. A frequent speaker on topics ranging from neurodiversity at work, to remote/distributed team culture, to product + engineering best practices, Jess is a champion of work that works for all, and being a voice for the underserved.