A professional decision-making nerd's 3 keys to take you from wanting to advocate for yourself to actually doing it
Her book is required reading at Stanford Business School. Now she's sharing some of her best advice with "Ask, Save, Earn"
Hi, my friend.
Meet Abby Davisson.
She calls herself a “professional decision-making nerd,” but she’s far more than that. She’s an author, a speaker, an advisor and a successful businesswoman, and she is on a mission to “help ambitious people stop agonizing over big decisions and start making them confidently.”
I didn’t know Abby, but I reached out to her after stumbling across a note she posted about pursuing a refund for something she had forgotten to cancel. (Who hasn’t done that before?) Once we connected, I knew she had so much wisdom to share.
Here’s our email interview, lightly edited…
Matt Schulz: First, could you tell me a little about yourself and your Substack? I also saw on your website that you've co-authored a book. I'd love to hear more about that, too.
Abby Davisson: After two decades of trying to change the world from inside big organizations – including running Gap Inc.’s corporate foundation – I decided it was time to repot my career.
I was great at helping organizations figure out their strategies, but I realized I wanted to help individuals navigate their biggest decisions, too. Years earlier when I was in grad school at Stanford, I'd taken a life-changing course taught by labor economist Myra Strober. That class stuck with me for over a decade as I climbed the career ladder, got married, and grew my family.
Eventually, Myra and I teamed up and developed a framework for tackling the trickiest decisions we all face – the ones where career ambitions and personal relationships collide. We turned that into a book: Money and Love: An Intelligent Roadmap for Life's Biggest Decisions. It became a top business book and is now required reading at Stanford's Graduate School of Business, which still feels surreal to me. The book is for people who want career success and personal fulfillment.
Now I've basically turned into a professional decision-making nerd. As an author, speaker, and advisor, I help people find the sweet spot between what they want professionally and what matters personally.
My Substack is where I geek out about this stuff regularly, sharing insights that actually move the needle on well-being. I'm obsessed with being intentional about everything (within reason, because nobody has time for that level of perfectionism). You can check it out at Practically Deliberate with Abby Davisson.
The short version? I help ambitious people stop agonizing over big decisions and start making them confidently.
MS: You said, "As an author, speaker, and advisor, I help people find the sweet spot between what they want professionally and what matters personally." What is the first step that people should take when beginning that process? And what do you think is the biggest mistake that people make in trying to do that for themselves?
AD: The first step is the same as in our 5Cs framework: Clarify what matters most to you. This isn't just about career goals — it's about understanding your core values, recognizing what life season you're in, and getting honest about what you actually want versus what you think you should want.
The biggest mistake? Letting other people's values masquerade as your own. We absorb expectations from parents, peers, partners, and society so completely that we mistake them for our personal preferences. I've fallen into this trap myself; it's surprisingly easy to chase someone else's definition of success while convincing yourself it's what you want.
As Aristotle said, "Knowing yourself is the beginning of all wisdom." Everything else flows from that foundational clarity.
MS: You've recently shared that you went through the process of trying to get a refund for something that you forgot to cancel. This is such a relatable thing, since I think most everyone has forgotten to cancel a membership at one time or another. Could you tell me what you did to try and get the refund and -- most importantly -- did you get it?
AD: Yes, I got the refund, but it took three tries and way too much time!
Here's what happened: [An online platform for legal services] jacked up my registered agent service by 60% without much notice. Instead of canceling immediately, I decided to do a full subscription audit first. Big mistake – I forgot to put it on my calendar (oops), and then I got hit with the higher charge.
I called to cancel and ask for a refund. The first agent tried to negotiate, then used scare tactics to imply that cancelling could put my business in "bad legal standing." When that didn't work, I asked for a supervisor who finally agreed to refund me after 30 minutes.
Plot twist: It turned out I only got a partial refund and the service was still active. I had to call again, this time using their "escalations" line. The third agent was actually helpful and processed the full refund in 10 minutes.
Total time invested: about an hour. The kicker? The refund amount was less than what I typically charge clients per hour.
The whole experience soured me on [the company]. I've found a better, cheaper alternative and won't be using them for future legal services. Sometimes the hassle of getting your money back teaches you more about a company than their marketing ever could.
MS: Are you someone who is generally comfortable doing things like asking for refunds, negotiating over things and advocating for yourself? If so, do you feel it comes naturally or is something you've had to learn. If not, how do you get past the discomfort when making those asks?
AD: I've gotten better at it over time, but I definitely had a head start.
My parents modeled this behavior. They taught me to speak up for myself. There's actually fascinating research by sociologist Annette Lareau showing that middle-class parents (especially white ones) actively teach their kids to question authority figures such as teachers and doctors and negotiate with adults in positions of power. That gave me a foundation many don't get. (For more on this, I recommend Lareau’s book Unequal Childhoods: Class, Race, and Family Life.)
Throughout my career, I built on that by negotiating with internal and external business partners alongside advocating for raises and promotions (both for myself and my team). Each success made the next ask easier.
Now that I'm self-employed, every dollar matters even more. When it's your own money at stake, you find the motivation pretty quickly. There's nothing like seeing your bank account balance to encourage you to pick up the phone and fight for what you're owed.
MS: In your book, you talk about decision-making and ambition. There are millions of Americans who want to do things like advocate for themselves, ask for raises, get credit card fees and waived and other such things, but they struggle mightily when it comes time to actually making the ask. What tips would you have to help people move from the decision to taking action?
AD: The gap between wanting to advocate for yourself and actually doing it is where most people get stuck, and I can absolutely relate.
We (especially women) have been trained from childhood to "be nice" and avoid conflict, but here's the truth: asking for what you want isn't conflict – it's being a smart self-advocate. Here are some tips that have helped me:
Start ridiculously small. I'm that person who always asks for a specific table at restaurants (much to my husband's embarrassment). But you know what? It works most of the time, and those tiny victories build your confidence muscle. When you've successfully negotiated for the booth by the window, asking for a raise feels less terrifying.
Do your homework before the big asks. Know exactly what you're requesting and arm yourself with information. When I asked for raises, I didn't just say "I deserve more money" – I came with benchmark data. Preparation is the antidote to that panic where your brain goes blank.
Flip the script in your head. You're not begging. You're presenting a business case. The absolute worst outcome is they say no, and you're right back where you started. But they might say yes, and that changes everything.
Here's what really convinced me to try: The person across from you handles these conversations constantly. Your manager has a budget for raises. Credit card companies have fee waiver protocols built into their system. You're not asking them to break rules. You're asking them to do their job.
The decision is just step one. Taking action is what actually moves the needle. My best tip? Treat yourself to some ice cream with the money you saved. That way, the victory is extra sweet (literally).
MS: How has the growth of AI tools like ChatGPT and Perplexity changed how people make decisions and their ability to feel more confident in advocating for themselves?
AD: The jury's still out on whether AI tools have fundamentally changed how people make decisions or advocate for themselves; these tools are simply too new for us to know.
When our hardcover launched in January 2023, our publisher ran ads showing someone typing into a Google-like search bar ("Should I move in with my partner?") with the tagline "Don't leave the big questions to a search engine." By our paperback release in April 2025, that same ad would have seemed quaint.
I'm a fan of using AI strategically, but success depends on asking the right questions. One powerful application: practicing difficult conversations before they happen. Need to ask for a raise or promotion? Have the AI play devil's advocate so you can anticipate pushback and refine your approach. This kind of low-stakes rehearsal builds the confidence that comes from feeling prepared when it really counts.
The key insight remains timeless: confidence grows through practice, whether that's with AI, a mirror, or a trusted friend.
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One of my favorite things to do is talk to interesting people about cool things they’ve done and what other people can learn from them.
Cases in point…
Have you done something awesome that you’d like to share because you think it could help others improve their financial lives? Then I’d like to talk to you.
Message me, email me or just leave a note in the comments below, and we’ll connect.
Until next time!
Matt