Michelle, 42, and Ryan, 43, love their three young kids. And spend a lot of money to show it. 

“I don’t say, ‘We don’t have the money, we can’t afford it.’ I don’t say those things,” Michelle told self-made millionaire Ramit Sethi on a recent two-part episode of his “I Will Teach You to be Rich” podcast. Their last names were not used.

Ryan earns nearly $140,000 a year as the sole financial provider, and the couple has a net worth of around $970,000. But they’re stressed about their day-to-day finances and constantly dip into their savings to cover their regular expenses. 

“It’s a sinking ship,” Ryan said. “It can’t continue this way because we will run out of money.”

Their fixed costs, including their mortgage, insurance, transportation and other necessities, total more than their monthly income. Plus, their spending has gotten out of control on what the couple calls “little things,” that just add up. Sometimes it’s necessary purchases like a carbon monoxide detector, but often it’s more discretionary like a beach canopy. They spend nearly $2,000 a month at Target and Amazon alone.

“You are losing money every single month,” Sethi told them. “You’re broke.”

Here’s why the couple feels stuck in their situation, and Sethi’s advice to help them to move forward.

When Sethi asked about their spending problems, Michelle and Ryan kept referring back to Target and Amazon purchases. 

In addition to necessities like groceries and diapers, the couple also rack up $15 to $30 impulse buys, such as kids’ sunglasses, soccer equipment and bike tires, that ultimately add up. “It really is death by 1,000 paper cuts on the Amazon front,” Michelle said.

Sethi wasn’t sold, however. Making a more conscious effort to cut out unnecessary spending can help, but the couple needs to look at the bigger picture, he said. 

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It’s not just that they make a lot of spontaneous purchases, but that they have no systems in place to help them make better decisions. When Sethi asked the couple where they could cut, Michelle was skeptical that she could significantly reduce those bills because many of those expenses felt necessary.

“This is what happens when you let your spending get out of control,” Sethi said. “It becomes incredibly difficult to downsize because the human mind convinces you that everything you have accumulated is absolutely necessary.”

He recommended looking at their big discretionary spending areas, like dining out and shopping at Target, and gradually cutting their spending by 50% over six weeks until they’ve stabilized. From there, they will hopefully be able to see things more clearly.

It’ll take an adjustment to start telling their kids “no,” but it will help their children develop a better relationship with money as they grow up, too, Sethi said.

Sethi doesn’t often tell people they’re saving too much money. But with Ryan and Michelle, it’s part of the problem.

Michelle takes pride in the way she built up her savings and investments by sticking to good habits throughout her 20s. Ryan wasn’t as prudent with his cash, Michelle said, but bought their house on his own before they got together. 

Overall, that has helped the couple amass around $585,000 in assets, including their home and nearly $468,000 in retirement savings and other investments. 

“In retirement we’re set, and right now we’re screwed,” Michelle said.

At the time of the podcast’s recording, the couple was allocating 14% of their take-home pay toward retirement and other post-tax investments. While that’s a great strategy to build up investments, especially while they’re fairly young, it doesn’t work with the rest of their monthly spending.

“When it comes to your spending, you’re spending way too much,” Sethi told them. “And when it comes to your investments, you already have enough if you were to literally stop today.”

The couple realized cutting back those monthly investments will give them the cash flow they need to cover their necessities and feel confident in splurging on things that are important to them but have gone neglected, like date nights. 

“The biggest breakthrough happened when they finally realized that they actually have control over their spending,” Sethi said. “It’s a nice cherry on top that they are over-investing so they can reallocate their cash.”

Check out part one and part two of Sethi’s conversation with Michelle and Ryan.

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To live a meaningful, fulfilling life, you have to accept that it’ll eventually come to an end, says Shoshana Ungerleider.

Over the years of caring for ill hospital patients, Ungerleider — a doctor who specializes in internal medicine — has observed regrets among people near the end of their lives, she tells CNBC Make It.

“Being proximate to the end of your life really allows you — pushes you — to be present because that’s all you have,” says Ungerleider, 44, host of the upcoming “Before We Go” podcast and founder of the nonprofit End Well Foundation. “That is true for all of us. Throughout our lives, this present moment is all we have.”

Here are five regrets she says people often express:

• I didn’t spend enough time with the people I love.
• I worked too much and missed out on life.
• I let fear control my decisions and didn’t take risks.
• I wish I’d been braver in the face of uncertainty or opportunity.
• I focused too much on the future and lost touch with the present.

Ungerleider’s advice for getting ahead of those regrets is simple: Remind yourself that your time is limited and unpredictable, and regularly ask yourself some big, important questions. How do I want to spend my time? What matters most to me in my life?

She particularly encourages young people, who often haven’t yet faced significant health challenges — in themselves or their loved ones — to think of that reflection as “really integral to living for a long, healthy life — with good quality of life.”

“As a doctor, I’d recommend eating a balanced diet, and exercising regularly, and avoiding things like smoking and high-risk activities. Reflecting on mortality should really be on that list,” she says, adding, “Reflecting on our own mortality throughout life, whether you’re 20, 50, 80, whatever, allows us to live better every day with more meaning and purpose in our lives.”

The mere acknowledgment that you’re going to die is a helpful way to find meaning in “the little things that bring us joy,” author Alua Arthur told “The Happiness Lab” podcast in a July episode.

“Grounding in my mortality means that at some point I won’t have access to all these senses anymore,” said Arthur, who’s also the founder of Going With Grace, a Los Angeles-based end-of-life planning and support organization. “And so, how cool is it that I can feel cold on my hands? How cool is it that I have plates for me to eat off of?”

Ungerleider’s observations are similar to those of Siddhartha Mukherjee, an oncologist and Pulitzer Prize-winning author, and Bronnie Ware, an author and former palliative care worker.

On their deathbeds, people often wish they’d expressed more love and forgiveness to people they care about, Mukherjee said in a commencement speech at the University of Pennsylvania in May. “Waiting [to express yourself] merely delays the inevitable,” he noted.

In Ware’s 2011 book “The Top Five Regrets of the Dying,” she wrote that the most common regret she heard was “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

“Many did not realise [sic] until the end that happiness is a choice. They had stayed stuck in old patterns and habits,” she wrote in a blog post. “Life is a choice. It is YOUR life. Choose consciously, choose wisely, choose honestly. Choose happiness.”

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Some people think asking questions — to friends, peers or bosses — can make you look weak or insecure.

But the simple act can actually help you garner influence and even get the people around you to change their minds, says communication expert Matt Abrahams — if you know the right questions to ask.

“Asking a question puts you in a position of power,” Abrahams, a Stanford University lecturer, tells CNBC Make It. “I can actually raise my status and lower your status when I ask a challenging question.”

Asking good questions “demonstrates you care, it demonstrates empathy, it demonstrates you’re willing to learn and, in some cases, admit you don’t know everything,” he adds. “Those are all valuable tools and assets to have when you’re trying to grow your career or deepen relationships.”

Effective leaders often balance their credibility with humility, a willingness to learn and connect well with their colleagues, experts say. But not every question will help you get ahead. You need to know how, when and why you’re asking the question for it to help make you more influential, says Abrahams.

Here’s how to ask the right questions, at work, home and in your social life, to get ahead and strengthen relationships, he says.

Good questions contain three elements, says Abrahams:

• They’re concise, so the listener doesn’t get distracted
• They build on what the other person has said — furthering the conversation, rather than paraphrasing or summarizing
• They revolve around a focused idea, or the conversation topic’s “bottom line”

“It can have multiple purposes,” but it should be quick, clear and focused enough so people understand the point of I’m trying to make,” Abrahams says.

You should consider your intention or goal before asking any question, he adds. Do you want show you’re listening and understanding, or that you’re very interested in the subject at hand? Maybe you want to subtly help the other person understand another perspective, or simply move the conversation along.

One of the worst intentions, Abrahams notes: trying to get participation points in workplace meetings. Your questions always need to be thoughtful, he says — if you aren’t helping clarify a point or furthering a conversation, your colleagues may just roll their eyes at you.

Asking good questions, especially to persuade, influence or change someone’s mind, takes practice. Start small, and try approaching your casual interactions like interviews, where you’re trying to learn more about the other person or conversational subject, recommends Abrahams.

If your questions often ramble, and you want to become more concise, he suggests turning to artificial intelligence: Ask a chatbot like ChatGPT for shorter ways to phrase specific questions, then analyze the results. You can also ask real people for feedback — after a big meeting or serious work conversation, find a trusted colleague and ask them what they thought of the questions you posed.

Above all else, always listen to other people before asking them anything, Abrahams says.

“Anytime you are listening, you’re doing yourself a service. You are showing the other person you’re here,” Abrahams says. Then, your question is more likely to feel like you’re “inviting the other person to collaborate, and solving the problem [together] helps you foster that relationship in the long-term.”

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First dates can feel like verbal land mines. You want to appear engaged but not nosey, and reveal enough about yourself without oversharing.

If you’re too concentrated on saying the right thing it can distract from the purpose of the date itself: getting to know the person across from you.

Aside from finances, most conversations are fair game, says Blaine Anderson, an Austin, Texas-based dating coach and founder of Dating by Blaine.

“There aren’t topics that are totally off limits,” she says.

Even typically taboo subjects can be addressed on a first date, and perhaps should be, if a potential mate’s opinion on them is a deal breaker.

“Politics can be a sensitive topic, but if you’re really passionate about politics and would only date someone who shares your viewpoints, then you’re probably better off bringing them up on a first date rather than waiting,” she says.

There are a few conversations that might sidetrack you from the goal of forming connection, though.

Here are three questions not to ask on a first date.

It’s tempting to inquire about a person’s last serious relationship or how they’re finding the current dating landscape, but questions like this are, to put it plainly, just not “fun,” Anderson says, something that a first date should be.

“The only category of questions I’d advise singles to avoid outright on early dates is around dating history,” she says. “There’s no need to bring exes into your first dates. Stay present, and focus on the here and now.”

One of the primary goals of a date is to flirt, which can only really happen if both parties are comfortable.

“Be playful, and ask questions that will make your date smile,” Anderson says. Prying about an ex is unlikely to do that.

Instead of nailing down the details of a second date while still on the first, take some time to think about whether you want to continue to get to know someone, says Grace Lee, a New York City-based dating coach and founder of A Good First Date.

“Planning for the second date is a form of courtship, a form of testing that mutual interest,” she says. “That’s why I like to leave the first date open. I like leaving that planning process intact. Now, one person has to take a little bit of a risk.”

Plus, she says, putting someone on the spot rarely encourages an honest answer.

“If you ask someone if they want to go on a second date, 99% of the time they’ll say, ‘yes’ because it’s so awkward not to say yes,” she says.

If you want to make it clear that you would like a second date, bring the conversation back to a restaurant or experience you both discussed.

“You can say, ‘We should totally check that out sometime,’” Lee says. “You’re alluding to something in the future, but you’re not asking them to do it.”

It’s generally a good sign if you don’t want the date to end, but that doesn’t mean you shouldn’t let it, Lee says.

“The problem with the seven-hour first date is you have this false sense of really being intimate without knowing if over time they will be consistent,” she says.

If you both feel a strong connection, you can continue to explore it on subsequent dates.

“As good as it feels, even if you’re on the most amazing date I’d encourage people to stop after the second round of drinks,” Lee says. “Leave wanting more. If the magic is there, it will lead to a second date.”

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You’ve probably worked with someone who’s always the loudest in meetings, talks over you and your co-workers, or takes more credit for projects than they deserve.

That’s the exact kind of anti-collaborative person who Sarah Paiji Yoo tries to steer clear from when hiring new employees.

“I like to lead as an open and collaborative leader. And I think that is a must-have for every team member that we bring on,” Paiji Yoo, the CEO and co-founder of eco-friendly cleaning product startup Blueland, tells CNBC Make It.

Anti-collaborative people can make for a particularly frustrating kind of colleague — even if they’re great at their job, on paper — often contributing to low morale, stunted productivity and broken workplace relationships.

“We like to hire people who aren’t coming in and saying, ’I’m the expert in this and thus, I should be able to make the final call,” says Paiji Yoo, 40. “Folks who understand that a different set of inputs, a lot of times, lead to a better outcome.”

Collaborative people don’t just appear friendlier in the workplace, according to Heidi K. Gardner, a leadership expert and distinguished fellow at Harvard Law School. They have a “major competitive edge” over their colleagues, because they typically “deliver higher quality results, get promoted faster, are [get] more noticed by senior management,” Gardner wrote for Make It last year.

“Being a collaborator isn’t easy. But the primary goal is simple: bringing people together to solve problems and learn something new,” Gardner added. “The mindset I always have is, ‘That person thinks differently from me. They know something different that I don’t, and I can learn a lot from them.’”

In 2019, Paiji Yoo co-founded Blueland and appeared on ABC’s “Shark Tank” to pitch the television show’s investors.

She and one of her early employees, Syed Naqvi — now Blueland’s chief innovation officer — launched their company in 2019. They appeared on ABC’s “Shark Tank” later that year, and secured an investment deal with Kevin O’Leary: $270,000 in exchange for 3% of the company and a royalty deal of 50 cents per product sold until O’Leary made his money back.

By 2022, Blueland had a total of $35 million in investor funding, over $100 million in lifetime sales and profitability. Paiji Yoo, who declined to share additional financial information, pointed to her company’s ongoing relationship with O’Leary — whose television persona is decidedly prickly — as an example of positive collaboration.

“He is always just a text or call away. We’re touching base by text or call, typically at least once a month. [In the] early days, it was like every week or every two weeks,” she says. “He’s been very engaged and very hands on with the business.”

The trick is to avoid coming across as transactional, says Paiji Yoo. Sending curt Slack messages or emails, or only talking to colleagues when they want something, can send a message to your co-workers that you aren’t interested in collaborating or building relationships.

“I think it’s more important than ever to come into work relationships with an open mind and assuming good intent,” she adds. “It’s [key] for innovation.”

She’s right, says Stanford University lecturer and communication expert Matt Abrahams: You’ll gain more workplace influence by finding allies and being helpful to the people around you.

“Check in with people and really listen when people say things to you,” Abrahams told Make It in March. “I’m not saying be manipulative. Buy [and respond] to the things you care about. Those are the things that, I think, can make a difference.”

Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank.”

Correction: This story has been updated to reflect that Syed Naqvi was one of Blueland’s early employees, and is currently its chief innovation officer.

Want to master your money this fall? Sign up for CNBC’s new online course. We’ll teach you practical strategies to hack your budget, reduce your debt, and grow your wealth. Start today to feel more confident and successful. Use code EARLYBIRD for an introductory discount of 30% off, now extended through September 30, 2024, for the back-to-school season.