Wayfair CEO: If you want to quit your job for your side hustle, ask yourself these 2 questions first
Quitting your day job to turn a side hustle into your full-time focus requires a leap of faith. You shouldn’t take that risk without first asking yourself a couple of key questions, according to Niraj Shah.
Shah, who co-founded home goods e-commerce company Wayfair in 2002 and serves as its CEO, believes budding entrepreneurs should be cautious when considering leaving the relative security of a full-time job for the uncertainty of running a business, he said on a recent episode of the “How I Built This” podcast.
“Often, if you don’t pursue something you want, you’ll have regrets,” Shah said. “But obviously if you do something reckless you could have different regrets.”
The idea of becoming your own boss and potentially building a successful, sustainable business can be tempting. It’s also a major commitment with no guarantee of success. Shah’s advice: Create a path to what he calls a “no-regret decision,” where “even if it doesn’t work, you’ll be happy you tried it.”
To do that, ask yourself two key questions to determine your level of conviction and financial readiness, Shah recommended.
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The first question: “Have you been able to progress [your business] to a point where you feel like it’s worth the risk and the effort of making it your full-time vocation?”
Think about your current level of confidence in the business itself — not just what you believe it can become, but where it actually stands now. Consider the specific goals of your business — from revenue targets to the number of customers or clients you want to be able to serve — and be realistic about how close you are to achieving them.
If you know what the business needs to do to survive and thrive, and you’re confident that “the odds of it working is high enough” to hit those goals with your full-time focus, then that’s an important first step toward taking the leap, Shah said.
Producing “recurring revenue” and a growing customer base are potential “green light” metrics that might suggest that your business could grow further with the right strategy and your full-time attention, podcast host Guy Raz suggested.
The second question is more personal and pragmatic, Shah said: “Are you in a position financially where you can afford to take that risk?” Billionaire serial entrepreneur Mark Cuban has worded a similar concept even more bluntly. “Save your money first. Don’t just leave [your job] unless you know what the hell you’re doing,” Cuban told Wired in October 2023.
“We hear all of these stories about all of these people who quit their jobs, started a company and made all of this money,” Cuban said. “What you don’t hear are the stories of the people who quit their jobs, started a company and failed miserably, and are now working at a job they hate.”
Some financial planners recommend putting aside enough money to cover your personal and business expenses for up to 12 months before quitting your job to run your own business full-time. Cuban suggested saving “at least six months” of living costs.
If you can’t ensure that you and your family would survive your business’ worst rough patch, you probably aren’t ready to quit your job yet, said Shah. You could, however, find alternative forms of financial preparedness beyond your personal savings — like asking friends and family for a loan or investment to give yourself more financial flexibility, he said.
“If you say you’re very convicted, then I would try to think through the money piece and figure out if there’s a path that makes it [worthwhile],” Shah said.
Alternatively, consider finding a creative “in between” option: If your employer doesn’t want to lose you, for example, you could negotiate reduced hours at your day job so you have more time for your side hustle, said Shah. Or, Raz suggested, hire a part-time employee to help you grow the side business.
Just be careful, Shah noted: Such arrangements could reduce your pay or cost you money, and damage your ability to financially protect yourself and your future business.
“I wouldn’t give up the job too quickly, for sure,” Shah said, adding: ”[But] is there something different than an all or nothing?”
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8 ‘joyful’ phrases people with high emotional intelligence use when making small talk
Over the last 10 years, I’ve hosted over 770 dinners, inviting everyone from Fortune 500 executives to strangers who just need a table to belong to.
My work and mission has always been to help people build community and feel a stronger sense of gratitude. I love watching new relationships form, whether it’s a professional contact or a new friendship.
A pattern I’ve noticed is that the people with the highest emotional intelligence at our events don’t care about coming off like the smartest person in the room. Their biggest priority is making their conversation partner feel seen and understood.
Here are eight joyful phrases people with high emotional intelligence use to turn small talk into genuine connections.
1. ‘It sounds like this is really important to you.’
This is an invitation to go beyond the surface. It demonstrates that you are paying attention to not just the words the other person is saying, but the feelings behind them. When you do that, you show yourself to be both observant and trustworthy.
2. ‘Your eyes light up when you talk about this.’
People rarely know how they come across, and this is an opportunity to tell them. When you mirror a non-verbal cue back to someone, whether it’s a genuine smile or an imperceptible shift in their posture, it’s not only a great compliment, but it can also help your conversation partner clarify where their passions lie.
3. ‘I love how you worded that question. It’s so unexpected.’
People with high emotional intelligence value curiosity. This statement shows that you aren’t just looking for simple, agreed upon answers, and that you want to know more about how they think.
In organizing these dinners, I’ve found that seeing how someone asks questions is actually a great way to get a better understanding of who they are and what drives them.
4. ‘I’ve never looked at it that way.’
In a similar vein, don’t be afraid to say “I don’t know” or “I hadn’t considered that.” These responses signal that you’re open to being challenged.
People with high emotional intelligence don’t always need to be right. They believe that life is more interesting when you leave yourself open to collaboration and discovery. This sense of humility makes them magnetic to be around.
5. ‘What made you smile today?’
Instead of “How was your day?” which can lead to vague recaps that grind conversations to a halt, this question gives the other person a chance to recall a specific moment of joy. It’s a small shift that inspires gratitude and deeper reflection. It is also a simple way to stay present.
6. ‘Who is someone on your team that’s doing something worth celebrating?’
This one is inspired by my friend Michael O’Brien’s work. He is an organizational expert and executive coach who developed a framework called Appreciative Enquiry, which is all about flipping negativity bias.
We’re so wired to be on the lookout for problems, but when you ask people to articulate what’s actually working, you can help them see what is possible.
This phrase is great when you’re in an office or networking context. It can help build a work culture that is driven by recognition, rather than criticism.
7. ‘Can we slow that part down? I don’t want to miss it.’
We live in a world that is often obsessed with instant gratification, but people with high emotional intelligence know how to slow down, and are generous with their time.
This phrase shows that you care enough to pause and lean in. This is one time when interrupting can actually be a positive thing for a new relationship.
8. ‘Tell me more…’
My friend and mentor Felipe Gomez, one of the most emotionally intelligent people I know, uses this phrase with me all the time. I’ll share some half-baked ideas, and he’ll simply say: “Tell me more.”
It allows me to think more expansively and go in any weird or whimsical direction I want without fear of judgment.
All of these phrases can help turn ordinary exchanges into genuine moments of intimacy and trust. However, if you’re in a new social situation and you start to draw a blank, don’t worry about trying to say the “right” thing. Just find a way to show the person you’re with that they matter to you.
Chris Schembra is the founder of the 7:47 Gratitude Experience, a consultancy that helps Fortune 500 companies and global leaders build stronger cultures of empathy, trust and belonging. A Wall Street Journal bestselling author and international keynote speaker, Chris writes about gratitude as a strategy for resilience, leadership and business growth.
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The top advice on aging from older Americans are all centered around these 7 themes
The well of advice for how to be healthier and live longer never runs dry. Those tips range from getting in enough exercise to eating a plant-based diet. One common piece of guidance urges us to form healthy, lifelong friendships.
To get some of this highly coveted wisdom from the older population in the U.S., Pew Research Center asked 2,582 Americans ages 65 and older a vital question: “Based on your own experiences, what advice would you give to younger people to help them prepare for getting older?”
“Respondents answered this question in their own words. We then coded their responses into categories based on the themes they mentioned, up to three per person,” the report states.
The topic that most of the older Americans gave advice on was health. Participants shared tips on how to eat, how often to exercise and the significance of staying up-to-date with medical appointments.
Centenarians that CNBC Make It has spoken to in the past have stressed the importance of eating mostly plant-based diets of whole foods like fruits and vegetables. Plenty of healthy adults over the age of 90 also mentioned the power of walking and moving your body as often as possible for longevity.
“I try to walk every day, without excuse,” Malcom Idelson told Make It in 2023 when he was 94. “I look forward to it. I’m often a little down and I say, ‘Let me get out and walk,’ and I feel so much better.”
Another factor that seniors found significant to highlight was finances. “While many older adults simply stressed the necessity of saving money, some went into more detail about investment strategies,” according to the report.
Here’s a full list of the themes that stood out of the aging advice from older Americans:
- Health (49%)
- Finances (37%)
- Mindset/outlook on life (24%)
- Relationships (11%)
- Activities (8%)
- Work (8%)
- Faith/religion (7%)
One of the top three topics was also having the right mindset or outlook on life. Nearly a quarter of seniors polled suggest that young people practice gratitude and enjoy life as much as they can.
When asked what her secret was for living a long, happy life, Roslyn Menaker told The Guardian, “I wear beautiful hats and go on daily walks – now in my wheelchair.” The publication interviewed her in 2023 when she was 103 years old.
“What else is important?” Menaker added. “Happiness, joy, appreciation. A positive outlook. Kindness and generosity. Try not to worry.”
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Trump CFPB aims to nix laws that ban medical debt on credit reports—it’s ‘salt in the wound’
The administration of President Donald Trump is taking aim at state laws that ban the inclusion of medical debt on consumers’ credit reports.
In late October, the Consumer Financial Protection Bureau released what’s known as an interpretive rule, stating that laws prohibiting medical debt reporting in 15 states are preempted by the Fair Credit Reporting Act.
Though the move is not legally binding, it marks an abrupt about-face from CFPB guidance during former President Joe Biden’s administration, which allowed states to make their own credit rules as long as they weren’t “inconsistent” with the federal law. A state requiring each credit agency to provide consumers with two free credit reports per year, for instance, would not be at odds with the FCRA, which requires one.
Consumer credit advocates are sounding the alarm. Millions of Americans are already facing the possibility of rising health-care premiums, a reality that could force more people into medical debt, says Chi Chi Wu, a senior attorney at the National Consumer Law Center.
Should medical debt protections fall, “now we’re going to make it even worse by ruining your credit record,” Wu says. “It’s just insult to injury. It’s rubbing salt in the wound.”
What’s at stake
Medical debt is a major source of financial insecurity among U.S. consumers. Americans owed about $220 billion in medical debt, according to a 2024 analysis from the Kaiser Family Foundation, with around 14 million people owing a debt of more than $1,000 and 3 million people owing more than $10,000.
The three major credit bureaus stopped reporting medical debts below $500 in April 2023. For the 15 states that have taken things a step further by banning any medical debt on credit reports, the rationale is simple, say Wu: Adding the data to credit reports is unnecessarily punitive.
The CFPB declined to comment on the reasoning behind the guidance. But the previous iteration of the agency spelled out why it says medical debt reporting hurts consumers.
“People who get sick shouldn’t have their financial future upended,” former CFPB Director Rohit Chopra said earlier this year. Reporting the debt, he continued, “has allowed debt collectors to abuse the credit reporting system to coerce people into paying medical bills they may not even owe.”
Essentially, allowing medical debt to appear on credit reports — whose related scores determine whether consumers can access credit or buy a home — puts the burden on consumers to navigate debt that is often sudden and difficult to understand.
For proponents of including medical debt on credit reports, “the argument is that the credit report is more accurate because there’s more information, and you don’t want to lend to someone who has a lot of medical debt,” Wu says.
But an April 2025 study from the National Bureau of Economic Research found that removing medical data from credit reports was “unlikely to affect credit outcomes.” That’s generally because people who have high levels of medical debt often rack up other kinds of debt to pay for treatment, Wu says.
“If you really are financially struggling from your medical debts, if you started off with an even halfway decent credit score, the first thing that happens is your credit card balances run up,” she says.
In other words, credit issuers likely have all the information they need to determine your creditworthiness, simply by looking at your credit card usage, which makes up a huge part of your score. Adding medical debt to credit reports amounts to kicking consumers when they’re down, says Wu.
‘It’s up to judges, not the CFPB’
Though the CFPB’s interpretive rule is perhaps the first step on the administration’s part to unravel medical debt reporting bans, the guidance itself isn’t legally binding. Rather, those laws would have to be challenged in court, says Brad Lipton, a former general counsel for the CFPB whose name appears on the Biden-era guidance.
“It’s ultimately up to judges, not the CFPB,” he says. The recent guidance, just like the one it contradicts, are merely pieces of evidence for a judge to consider.
In the meantime, the state bans “haven’t been super controversial,” he says. The reason, he says, is that credit reporting of medical debt is not a big driver of payment of medical bills.
“If someone doesn’t pay their medical debt, it’s usually because they simply don’t have the money,” he says. “The government and the system can torture them all they want, but you’re just not going to get much money out of it. It’s water from a stone.”
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28-year-old engineer laid off by Amazon in 2023 on how she bounced back: ‘Don’t sit by yourself and just keep overthinking’
Shreya Bhosale felt deja vu when Amazon announced last week it was laying off 14,000 corporate workers.
She knew exactly what so many people were suddenly going through. Bhosale, 28, is a tech worker in Seattle and was among the 18,000 Amazon staffers laid off in January 2023.
Bhosale tells CNBC Make It that two years ago, she’d heard rumors of potential layoffs swirling in news reports. By the time she received notice that she’d been let go, she says it was “a complete shock” and “disappointing” to learn the news via email.
“It was just out of nowhere, and it definitely took a toll on my emotional health,” Bhosale says. “It disrupted my sleep. I had a lot of self-doubt. There was difficulty in eating [and] constant anxiety.”
Adding to her stress, Bhosale was hired to Amazon as an engineer just out of grad school as an international student from India, and her layoff put her work visa and ability to stay in the U.S. in jeopardy.
Bhosale says today’s job market is a lot more challenging today than when she was laid off. Workers are fighting for a shrinking pool of job openings, AI is seemingly threatening jobs and long-term unemployment is inching up.
That said, she says she learned four big lessons from her own layoff that might help people going through it today.
4 ways laid-off Amazon worker bounced back
First, Bhosale says she wish she didn’t internalize the shame of losing her job. She says she’s noticed people are becoming more open about being laid off these days, but just a few years ago, there was still a heavy stigma around it.
It took her time to accept that the layoff wasn’t a reflection of her abilities, but rather a decision made by the business. Now, “people are very empathetic towards each other. People are reaching out and helping in any way they can,” she says.
Second, Bhosale recommends resisting the urge to withdraw, and instead stay in touch with other people, whether they’re friends or potential networking connections.
“Reach out to people,” Bhosale says. “Even if you are not feeling good today, just pick up your phone and call your friend and say, “Hey. This is what’s happening. I feel really sad.′ Just talk. Don’t sit by yourself and just keep overthinking in the situation. I didn’t find that helpful.”
Check online or on social media for communities intended to help laid-off workers find job leads, get referrals, that offer job resume or job interviewing help, and more.
Next, as much as you’re financially able to, Bhosale recommends taking time to deal with the shock of your layoff so you don’t burn out in your next job search.
Bhosale says she learned this lesson the hard way.
“Take some time to heal. Don’t just push yourself to find another job,” Bhosale says, adding that because of her visa situation, she pushed herself to find her next position within six weeks of her layoff, which led to burnout that affected her next job.
“Even when I started my new role, I was always afraid of, ‘What if I do something wrong? Will they lay me off again?’” Bhosale says the lingering anxiety stuck with her for a year until she processed the layoff and that she would be able to find her way out of another situation if it happened.
Finally, Bhosale recommends people start upskilling in their own time, like through LinkedIn courses, especially to incorporate AI into their work. “There are so many new technologies, and companies are looking to work with people who have that knowledge.”
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