How to Build a Business That Works Around Your Life With Holly Haynes
What if you could grow your business and get your life back at the same time?
That’s the exact question we explored in this episode of The Lazy Entrepreneur Podcast, featuring business strategist and podcast host Holly Haynes — a woman who left corporate America to design a life centered on freedom, purpose, and profitability.
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After 22 years in corporate strategy, Holly started her business at 41 and built it into a thriving company that now helps other entrepreneurs grow and scale — without chasing trends, working 24/7, or sacrificing what matters most.
If you’ve ever felt stuck in hustle mode, constantly creating new offers or content but still craving peace and time freedom, this conversation will give you a roadmap to reset how you run your business — and your life.
From Corporate Strategy to Freedom Lifestyle
Holly’s story isn’t your typical “quit-your-job-and-follow-your-dreams” narrative. She had a secure corporate career and deep experience in business strategy. But despite the success, she felt like something was missing — freedom.
“I didn’t start my business until I was 41,” Holly says. “I wanted to take everything I learned from Fortune 500 companies and make it simple and practical for small business owners who want flexibility, not burnout.”
Today, she helps entrepreneurs grow consistent, high-paying clients while building lives they actually enjoy. Her signature message?
You can scale your business without sacrificing your sanity.
Why You Should Stop Annual Planning (and What to Do Instead)
When most business owners think of goal setting, they wait until December or January to plan the year ahead. Holly says that’s one of the biggest mistakes entrepreneurs make.
“I don’t wait until the end of the year. I do what I call a quarterly lookback analysis — every 90 days.”
Her process is simple but powerful. Every quarter, she reviews her Business Scorecard, which is basically a spreadsheet with a mix of data-driven and reflective questions like:
Where did our sales come from?
Which marketing channels performed best?
Did we get a good ROI on what we invested in?
How is the team doing?
What felt fun and fulfilling — and what didn’t?
This combination of metrics and mindset creates a 360° view of your business. It’s not just about numbers — it’s about alignment.
When you track progress quarterly instead of once a year, you catch problems sooner, pivot faster, and take the pressure off.
“If I try something and it doesn’t work, I’m not tied to it for 12 months,” she says. “I just adjust next quarter.”
This shift alone can save you from decision fatigue — and turn your business planning from stressful to strategic.
Plan Your Business Around Your Life — Not the Other Way Around
Holly believes most entrepreneurs build their calendars backward. They fill their schedule with work, meetings, launches, and tasks — then try to squeeze in family, self-care, and fun around it.
She does the opposite.
Every quarter, she starts by asking:
What season of life am I in right now?
What do I want my next few months to feel like?
What personal priorities matter most — family trips, rest, hobbies, time off?
Then she layers her business goals around her life.
“Think of it like a puzzle,” she says. “Put your life priorities down first. Then your business goals fit in around them.”
This approach doesn’t just make her business more joyful — it keeps her motivated and creative. She’s not chasing constant growth for the sake of growth; she’s building a business that supports her lifestyle.
Where High-Paying Clients Really Come From
Every entrepreneur wants consistent, high-paying clients — but Holly says most people are looking in the wrong places.
“High-ticket clients come from relationships,” she says. “Not from someone seeing your reel one time.”
That doesn’t mean you should ignore social media. It means your real connections matter more than algorithms.
Holly teaches entrepreneurs to build depth behind the visibility. A viral post might get attention, but meaningful conversations, referrals, and testimonials build trust — and trust leads to sales.
“Someone’s not going to hand you $10,000 unless they trust you,” she explains. “They need to see your face, hear your voice, and feel like they know you.”
That’s why her business thrives on personal connection — through podcasting, emails, and long-form storytelling that lets people see the human behind the brand.
The Power of Sharing Your Story
Many business owners underestimate how powerful their personal story is. But according to Holly, your life experience is your competitive advantage.
She often reminds her clients that people don’t just buy products — they buy relatability.
“Most of my clients know I have twin daughters, that they’re in middle school, that they just got braces. None of that has to do with my programs, but people relate to it.”
The takeaway? Share your real life. You don’t need to reveal everything — just enough to make people feel like they know you.
That’s how you stand out in a digital world that’s flooded with polished, impersonal content.
Why Relationships Will Always Outperform Algorithms
Holly and I talked about something deeply relevant in today’s business climate — what some call the trust recession.
In a world where AI, automation, and online noise dominate, people crave authenticity and connection.
“Everyone can create content now,” she says. “But what can’t be replaced is relationship. Collaboration. Empathy. Real connection.”
That’s why Holly teaches entrepreneurs to focus less on trends and more on relationships that build long-term loyalty.
Whether it’s nurturing your clients, networking with peers, or connecting with your audience — the human element will always win.
A Stress-Free Way to Start the New Year
Most entrepreneurs treat January like a sprint. New goals. New launches. New everything.
Not Holly.
“I’ve taken all the pressure off the start of the year,” she says. “January is my recharge month.”
She uses that time to rest, reflect, and realign her energy. Her calendar for January is blocked off — no big projects, no launches, just intentional space to recharge.
This rhythm follows what she calls seasonal alignment:
Winter → Rest, recharge, reflection
Spring → Growth and learning
Summer & Fall → Execution and momentum
“The calendar is made up,” Holly laughs. “Make up your own version that fits your life.”
It’s a refreshing reminder that success doesn’t have to be linear or frantic. You can grow and rest — at the same time.
Systems, Support, and Letting Go
As Holly scaled her business, one of her hardest lessons was letting go of control — especially over her inbox.
“For the longest time, I thought nobody could answer emails better than me,” she admits. “But once I delegated part of it, I realized it saved me hours every week.”
Her advice for entrepreneurs who struggle to delegate?
Start small. Hire for a project or season, not a full-time role right away. Build trust gradually.
She also recommends the book “Who Not How”, which helped her reframe delegation as a growth tool, not a risk.
“It’s impossible for one person to do everything,” she says. “Even successful people have great teams behind them.”
How to Take Tiny Steps Toward Freedom
When asked how she built a business that now allows her to take weeks — even months — off, Holly’s answer was simple: baby steps.
She didn’t leap from corporate to freedom overnight. She started small:
No meetings on Mondays.
Then no meetings on Fridays.
Then taking one week off every quarter.
Eventually, building systems that let her take an entire month off — without stress.
“You don’t need to overhaul everything,” she says. “Just take one small intentional step at a time. They add up.”
That’s the spirit of sustainable success — progress without pressure.
Holly’s Final Wisdom: Learn from Every Step
At the end of our conversation, I asked Holly a reflective question passed down from my last guest:
“Is there anything you’ve done in your life that, if you had to do it again, you wouldn’t?”
Her answer was beautiful:
“My gut answer is no. Everything happens for a reason. Even the things that didn’t go as planned taught me something that led me to where I am today.”
It’s the perfect message for entrepreneurs who are hard on themselves — a reminder that every challenge, mistake, or slow season is part of your growth story.
Where to Find Holly Haynes
You can connect with Holly on her website at hollymariehaynes.com and listen to her podcast Crush the Rush, which has over 600 episodes of strategy, productivity, and mindset tips for women in business.
