Hi Realists! 👋

Welcome to Cup of Ambition, Volume 11!

In this edition, you’ll get the scoop on:

‼️‼️ 9-to-5 Dilemma: When Your Job Search Feels Like Defeat

📌  Should You Email the CEO?

🆘 Interview Prepping in 2024

💗 2024 EmpowerHERR Recap

9-to-5 Dilemma.

“Well, I’m coming up on a year of unemployment and I still haven’t found a job. To say I am defeated, depressed, humiliated, angry, depleted, and utterly kicked in the gut is an understatement.

I’ve applied to more than 1,500 jobs, but I’ve only had 8 phone interviews and 2 interviews, both of which turned me down. I used to think I was pretty good at my job— I got bonuses, I was invited to participate in new projects and launches, and I generally enjoyed what I was doing. Now, I’m pretty sure no one is interested in even talking to me.

To say that I’ve lost my confidence is an understatement. This whole process has rocked me to my core and most days it’s a struggle to even get out of bed and look for jobs.

I’m not sure if you can help me or give me some kind of encouragement, but I’ll take anything I can get right now.”

-Down Bad.

_____________________________________________________

Dear Down Bad,

First, let me say this: You are not alone. The feelings you're carrying are valid. Losing confidence after a year of relentless job searching is understandable, but here’s something I need you to hear—you are still good at your job. That hasn’t changed, even if the broken, effed up process has made you question it.

When it feels like you've lost control, it's easy to start doubting your value, especially when the silence after 1,500 applications feels deafening. I’m not going to sugarcoat it—this job market is tough. But it’s not a reflection of you. It’s a reflection of the process, a system designed to filter, scan, and often overlook talented people.

Being unemployed is not a character flaw. Unemployment is not your forever state. This is a bleak, dreary stop on a longer journey.

Now, let’s get tactical.

1. Focus on your wins: This isn't about resume bullet points, it’s about reminding yourself of who you are and what you bring to the table. Write down your biggest achievements, the ones that lit you up and showed your impact. You got bonuses for a reason. You were chosen for projects for a reason. Let’s bring that front and center.

2. Change your strategy: Applying to 1,500 jobs shows grit, but let’s redirect that energy. Instead of sending out mass applications, focus on relationship-building and running clear lanes.

Pick an industry, job title, company size, or other criteria and run that lane full speed. Tailor your outreach and experiences to what matters to decision makers in that space. Once you’ve run that lane, pick another. Be intentional and strategic about where you’re focusing instead of a one-size-fits-all approach.

Who can you talk to in your network? What are the key companies you’re genuinely interested in? Start creating intentional connections with decision-makers in those spaces.

3. Be your best advocate: I know this process has taken a toll on your self-confidence, but I need you to advocate for yourself like you would for a friend. Speak up about your value. Write it down, say it out loud, get used to hearing your wins. You are your best hype person, even if you feel like you can barely muster a whisper.

You’re in a valley right now, but this isn’t the end. The right opportunity is out there, and it’s going to come from a place where you’re not just another application. You’re a person who’s still standing despite the hits—and that kind of resilience is worth gold.

This isn’t about toxic positivity or telling you to suck it up, it’s about survival of your wellbeing. One step forward a day is closer to the goal, just keep swimming.

Please, I Beg You… Don’t Email the CEO.

I’ve seen articles like this one making the rounds, encouraging job seekers to bypass traditional channels and DM executives directly. Sure, this approach can work for some, but let’s take a beat before we all jump on the DM train.

First, I’m a big fan of being bold in your job search. If you've built a solid connection or meaningful interaction with a leader, then sending a direct message with intention can absolutely be powerful. But sending a cold DM just because you found the CEO on LinkedIn? That can come across as a bit… presumptuous.

During my time in recruiting, I saw this play out time and again. People would message leaders saying, "Hey, I’ve applied to your company—let’s set up a time to meet." What they didn’t realize was that these messages often landed on deaf ears. Many leaders were uncomfortable with unsolicited requests, especially when there was no prior relationship or reason to engage beyond the cold application. In some cases, it even hurt the applicant’s chances because it felt like they were bypassing the process. The managers would come to me and ask “What am I supposed to do with this?” Instead of making them stand out, it made them seem more focused on jumping the line than building a genuine connection.

So, when can a message be effective?

A DM can be incredibly effective when it’s the right person, at the right time, with the right message. Here’s what that looks like:

1. Warm up the connection: If you’ve been following the company, interacting with their posts, or have mutual connections, you're in a stronger position to send a meaningful message. Take the time to build rapport. Comment on their posts, engage in thoughtful discussions, and get on their radar before you hit send on a direct message.

2. Craft a message with value: Instead of, "I applied to this role—can we meet?" focus on how you can add value. Mention why you’re genuinely interested in the company, highlight a relevant connection or insight, and position yourself as someone who can solve a problem for them. Example: "I saw your recent post about [X challenge]. I’m really excited about how my experience in [Y solution] could help your team overcome that. Would love to connect if you have time."

3. When to reach out: A well-timed message can make all the difference. If you’re responding to a company announcement, a shared industry challenge, or a major project they’re working on, your message is more likely to resonate. Timing matters—avoid sending a DM just because you applied. Instead, align your outreach with a moment that shows you’re paying attention and thinking strategically.

Sliding into DMs won’t replace the need for a strong personal brand, a tailored resume, and relationships built on trust. But if done thoughtfully, reaching out to a decision-maker can open doors—if you bring value to the conversation.

Remember, in this market MOST people are sending the same message: “Hi, I applied for this job. Can you help me?” If you’re going to take the plunge and cold outreach network, don’t lead with an ask, be thoughtful, and make it personal.

So, before you hit ‘send,’ ask yourself: Is this the right move for me, my industry, and my target role? And how can I make sure my message stands out as thoughtful and intentional, not just another attempt to bypass the process?

The Right Way to Prep for an Interview

(Hint: It’s Not Spending 6 Hours Researching the Company)

I often ask clients to walk me through their interview preparation process. A lot of times they’ll say something like, “first, I spend about 3-4 hours researching the company, reviewing annual reports, making notes on their values and history, researching the leadership team, reading reviews…” When I ask about how long they spend prepping answers and tailoring responses to critical factors of the role, most people “just kinda wing it.”

While understanding the company is important, interview prep is not about spending hours diving into every page of their website or memorizing their last five years of annual reports. That’s not going to make or break your interview.

The real goal of interview prep? To clearly communicate how your experience aligns with the role and show up as the solution to their needs.

You should be spending the most time pre-interview on the self-work, less time on the company research.

1. Know Your Story 

Before you jump into company research, get clear on your story. What are your top three career achievements that align with this role? How do they demonstrate your impact and the value you bring? Be ready to explain how your past experiences have prepared you to take on this position.

2. Align Your Experience with the Role 

Don’t just skim the job description. Break it down. Highlight the key responsibilities and required skills, then connect them to your own work history. How have you handled similar tasks? What successes can you share that demonstrate your ability to excel in this role? Interviewers want to see that you understand the role and can hit the ground running.

3. Focus on Value, Not Company Trivia 

Yes, you should know some key facts about the company—its mission, products, recent news—but what they really want to hear is how you can solve their problems. Instead of rattling off facts about the company’s history, use that information to connect back to your experience: "I noticed your recent expansion into X. I’ve led initiatives in Y, which could really support that growth."

4. Prep for the Questions That Matter 

Anticipate the tough questions. Know how to answer behavioral questions using the PAR (Problem, Action, Result) method or BLUF (Bottom Line Up Front). Practice telling impact stories that highlight how you’ve contributed to your previous employers' success and how you can bring that same value to their team.

5. Have Questions That Show You’re Thinking Long-Term 

Finally, don’t just ask questions for the sake of asking. Show that you’re thinking about how you can contribute to the company’s future. Questions like, “How does success look in this role six months from now?” or “What challenges is the team facing, and how can someone in this role address them?” demonstrate that you’re already thinking strategically.

Bottom line: Interview prep isn’t about burying yourself in research. It’s about showing up prepared to articulate your value and align it with what the company needs. Focus on what you bring to the table, and let your story do the heavy lifting.

2024 EmpowerHERR Women’s Conference Recap

I had the absolute BEST time at EmpowerHERR last weekend! I met so many incredible women who were all there to make an investment in their wellbeing (shout out to all the new newsletter subscribers that I met!).

I hosted a Brunch and Learn session focused on breaking up with brag shame and how to build a career brand that’s too good to ignore. When I opened it up for questions, I heard from women in all phases of their life and career.

“I keep starting over in new roles because where I go doesn’t pay me what I know I should be making.”

“Am I allowed to ask questions in an interview? I was always taught to be thankful to be invited into the room.”

“How do I even build my brand when I’m new to Real Estate and I’m still unsure of what I’m even doing?”

“I’ve had the same resume since… I can’t remember when. Where do I start?”

Often times we feel like we’re the only one in these career bumps, setbacks, inequities, and challenges. There’s just something about coming together in a room and hearing other people say that they feel it too, they’re unsure and unsteady too, or they’ve never stopped to repair their view of themselves and their brand.

In an earlier session, I asked a panel of breast cancer survivors what advice they would give to their younger selves. The responses from women who have faced death and kept going were perspective shifting. One response stuck with me and I keep thinking about it…

“Be present, not perfect.”

Man did that hit me. How often in your life are you so focused on making sure the details are perfect, that we’re perfect, the timing is perfect, the circumstances are perfect… and we lose sight of just being present?

One woman shared how she waited until she was 50 before finally acknowledging and honoring what she loves… teaching dance. She built an offer too good to refuse, took it to local community organizations, and was offered a role with the Cincinnati YMCA. And she finally feels like she’s being present with who she is and what she loves.

If you’re waiting for the perfect time, perfect job, perfect credentials/experience… the time will never come. Do it anyways, do it scared.

I walked away with a stronger sense of community and a renewed sense of my purpose. I met wonderful new women, many of which are already on the books for coffee, and I just love that. ☕

Dollyism.

Don’t Be a Stranger!

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