( ENSPIRE Business ) Hawk Collaborates With TurboTax & Their Experts for Business Program
Jereshia Hawk is a trailblazing entrepreneur and mother who took a leap of faith from engineering to building a multi-7-figure coaching business. Her story starts when she began building a careful bridge before transitioning career paths. Once a solid plan was in place, she left her corporate job to pursue her own business. The growth was astoundingly fast; by her fifth year in business, she made $1M in profit. Although all her career aspirations were fulfilled, Hawk began to realize that money wasn’t the main driver of business growth. However, it did bring stability and enabled her to create opportunities for others. Slowly but surely, she was redefining what success meant to her, earning profits while also aligning her business with her values and goals beyond the industry.
Hawk soon decided to take a break and plan out her sabbatical. Most business owners don’t take a sabbatical until they burn out or are forced to take a break. In 2019, she was inspired by a couple she met in Bali to take a sabbatical during the seventh year of her business. Hawk’s prior strategy was to take several months to prepare and test the department of her business to ensure they could handle it well while she was away. During her sabbatical, there was an amicable divorce, the death of her father, and self-discovery. She soon realigned her priorities, and she de-scaled her business, putting it on the back burner to support her personal needs, life, and fulfillment. Hawk placed significance on her profits based on what she wanted in her life: a happy family, great relationships, good health, hobbies for pure enjoyment, all while her business supports these goals rather than dictates them.
Hawk offers her coaching-based services for any side gig and business. All services are designed with intention, with every piece of advice and refinement tailored specifically to the owner and the business model. Coaching is more than strategy; it supports both your financial goals and your life. Three prime services she offers are the Cashflow projection calculator, Market Like A CEO™, the course, and Work With Me 1:1. Firstly, the Cashflow projection calculator is a tool for business owners who want to see their business plan through numbers, revenue needed, clients required, and month-by-month cash flow timing.
Next, The Market Like A CEO™ explores the discernment and delivery of a business by showcasing it to new and current clients through messaging that explains why your business matters and sells your perspective. Lastly, the Work With Me 1:1 is a consultation where business owners discuss the business plateaus they are experiencing and how to refine how things operate from the inside, using Hawk’s resources to help sustain and deliver more profit, all while maintaining freedom and reducing dependency on you, the owner. Currently, Hawk is paying it forward by collaborating with TurboTax and their Experts for Business Program. This program helps entrepreneurs understand the financial side of running a side gig and business.
Your transition from a $150k engineering career to a multi-7-figure business is a blueprint for many. Using your engineering background, what specific ‘stress test’ should a professional run on their ‘bridge’ before they decide to quit their 9-to-5?
Entrepreneurship is often romanticized right now. You see revenue screenshots. Big launches. Stories about someone quitting their job in what feels like an overnight decision of faith. But the way I approached my transition was less about leaping and more about building a bridge, giving myself optionality and choices rather than it feeling like an all-or-nothing decision. For me, that meant being very intentional about replacing my corporate salary before leaving my career. I want to confirm that my business can support long-term financial stability. So instead of treating my job like something I needed to escape from, I allowed it to fund the development of my new business. It gave me options. It gave me time to learn.
The biggest stress test I ran was revenue consistency. I want to generate consistent revenue for 12 to 18 months, not just one or two lucky launches. I was looking for a trend line of increasing predictability, not just spikes. Because spikes are exciting, but they don’t build stability.
I was also pressure-testing something deeper: myself. Entrepreneurship requires a different level of discipline and self-management. I wanted to see if I could stay committed even when I didn’t see immediate results. Could I keep showing up? Could I keep refining my approach? Could I stay focused without a boss or a corporate structure holding me accountable?
And then there was the sales side of the business. I needed to know if I could:
- Articulate my perspective clearly in my marketing
- Show up publicly and be willing to be seen
- Lead sales conversations confidently
- Support prospects in making buying decisions
I also had to pressure test my mindset around pricing. Could I say my prices out loud without hesitation? Did I believe in the value of what I was selling? Was I confident I could deliver results for the clients who trusted me? Those are the kinds of tests that actually tell you if the bridge is strong enough. For me, the goal wasn’t to feed off a moment of momentum. The goal was to build a foundation where the business had predictable revenue, strong sales skills, and the personal discipline required to sustain it long term. After 18 months, bringing in $150k in revenue and being consistent with my sales activities, I knew I was ready to cross that bridge and give my business my full attention.
In your experience coaching side-hustlers, what is the most common ‘logic trap’ or flaw they fall into when trying to cross over into full-time entrepreneurship?
In my experience coaching side hustlers, the most common logic trap they fall into is believing that being great at the work automatically translates into building a great business. Most people starting a side hustle already have real experience doing the thing they want to sell. They might be excellent at delivering a service, teaching a skill, or executing a strategy. They’re comfortable being head down and doing the work. But what they often underestimate is that business doesn’t pay you simply based on how good you are at the job. It pays you based on how clearly you can articulate the value of what you do, how effectively you can sell it, and how much demand exists for the solution you provide.
The real hurdle is the shift from an employee mindset to an entrepreneurial one. As an employee, your job is to execute. You’re rewarded for being reliable, skilled, and consistent in your role. As an entrepreneur, however, your responsibility expands beyond delivery. You have to actively generate demand for your work. That means learning how to communicate your perspective, articulate the transformation you provide, and show up publicly so people understand who you are, what you do, and how you help.
Many side hustlers are incredibly capable at delivering their services, but they have to overcome the discomfort of promoting themselves and making their work visible. They have to learn how to show up in their marketing, share their thinking, and lead conversations that help prospects make buying decisions. Because if the market doesn’t clearly understand the value of what you do, doesn’t understand your perspective on the work, which differentiates you from others, it doesn’t matter how talented you are behind the scenes. Otherwise, the risk they run is becoming the best kept secret, incredibly talented, highly capable, but largely invisible to the very people who need their work the most.
In 2019, you chose to descale your business. Walk us through the ‘identity friction’ you felt: how did you reconcile the internal need for a sabbatical with the external industry pressure to ‘keep scaling’?
Externally, my business was doing incredibly well. I wasn’t trying to escape a broken business. I was confronting the reality that even with millions being made every year, healthy profit, a lean team, clients I loved, and spaciousness in my calendar, I still felt deeply disconnected from myself. My personal life was unraveling in ways my business success could no longer distract me from, and I had to face a hard truth: I was self-soothing, but I was not self-caring. My business had become a coping mechanism, I wore the title of “workaholic” with pride, and the industry pressure to keep scaling made it very easy to confuse constant growth with alignment.
The deeper reconciliation came when I stopped measuring success by how much more I could produce and started asking, “How much is enough?”
That question forced me to reexamine my owner’s intent, my lifestyle, and the kind of life I was actually trying to build. I loved my business, but I wanted to love my life, outside of work, more. I realized I didn’t want to keep scaling just because the market rewards that story or simply because I could. I wanted to build from a deeper meaning, significance,e instead of survival. So the sabbatical was not me walking away from ambition. It was I who chose a more honest definition of success. And that required letting go of an identity that was overly attached to productivity, resilience, and proving. Slowing down felt terrifying, but on the other side of that decision, I found that giving myself permission to pause did not ruin my life or my business. It helped me return home to myself.
You’ve described your sabbatical as a ‘strategic test.’ What was the most surprising ‘weak link’ that surfaced in your absence, and how did fixing it shift your business from a ‘hustle’ to your current ‘Sustainability and Significance’ model?
The most surprising weak link that surfaced during my sabbatical planning wasn’t actually an operational issue. It was an identity attachment I didn’t realize I still had around sales and revenue generation. Before the sabbatical, I had already engineered most parts of the business to function without me. Client delivery was curriculum-based. Program coaches were trained in our frameworks. Marketing systems were documented. Operations were lean and structured. From a structural standpoint, the company was already very stable.
Then life forced the real experiment before I was ready. A family member passed away the week before a launch. I flew back home to Michigan. I was offline, I was grieving, I was completely unavailable. And my team ran the entire launch without me, qualified leads, nurtured conversations, closed sales, all through DM. No calls. No check-ins. No me. It was our largest cash-collected month ever in business.
And instead of feeling relieved? I felt disoriented. Because somewhere along the way, I had quietly attached my worth in the business, my identity, with being the one who made the money happen. Hustle was me being the nucleus of every transaction, every result, every revenue-generating decision.
My energy was the fuel source, which meant the business was only as sustainable as I was, and I wasn’t built to run at that pace forever. The sabbatical didn’t just stress test the business. It stress tested me. And the weak link it exposed wasn’t in my operations; it was in how tightly I was holding on to a version of myself that the business had already outgrown.
Through your work with TurboTax, you advocate for cash flow mastery. How does having a ‘data-backed’ projection calculator empower a CEO to stay objective when personal life events or market plateaus create emotional turbulence?
When life gets hard, and it will, you don’t want to be making financial decisions from a place of fear or grief or panic. You want data to be the thing that steadies you.
That’s really what a cash flow projection tool does. It removes the emotion from the equation, not because emotions don’t matter, but because your feelings about money and the actual math of your money are two very different conversations. And when you’re in the middle of a market shift, a personal loss, a slow month, or any kind of turbulence, those two conversations will absolutely collide if you don’t have something concrete to anchor you.
Knowing your numbers isn’t just a financial skill. It’s an emotional regulation strategy. CEOs who lead from data don’t make better decisions because they’re less human. They make better decisions because they’ve already answered the financial questions before the emotional pressure hits.
Your Market Like A CEO™ course emphasizes ‘perspective over information.’ In an era of AI-generated content, how can a leader cultivate the ‘discernment’ necessary to ensure their brand voice remains original and evolves alongside their personal growth?
Here’s what I know to be true: AI can replicate information all day long. What it cannot replicate is your lived experience, your discernment, and the specific way your worldview shapes how you see a problem and solve it. We are in an era where information is everywhere, and it’s free. Your most qualified buyers are not searching for more information. They are searching for someone whose thinking they trust. Someone whose lens on the world matches the level they’re trying to operate at. That’s a completely different thing to sell, and it requires a completely different way of showing up.
The discernment piece is really about self-awareness. It’s about knowing what you actually believe, not just what the industry has trained you to say. And honestly? Most experienced business owners have developed really rich, nuanced perspectives. They just haven’t learned to say them out loud yet. They’ve been so focused on explaining what they do that they’ve never fully claimed how they think.
AI can generate content. It cannot generate conviction. It cannot generate the specific tension you hold between two competing truths. It cannot generate the things you learned by living through something and the real experiences you gained. That’s yours. And that’s what your most aligned clients are actually buying.
So the way you stay original isn’t by trying to out-create the algorithm. It’s by going deeper into yourself. It’s by asking, regularly, “Has my thinking evolved and does my messaging reflect that publicly?”
Jereshia Hawk’s coaching services are all about having a strategic partner who understands where you are, emotionally and strategically, with your business. To help you make decisions that lead to profit, sustainability, and align with your personal goals. There is no cookie-cutter roadmap; Hawk will help you develop a personal map tailored to your lifestyle. This includes honing your focus and streamlining operations with intention. In other ways, Hawk shares her wisdom and stories as an entrepreneur through the Jereshia Said Podcast. Many behind-the-scenes minutiae of running a significant business in the online world, all while gaining valuable insights that will help other business owners make money. To explore more of Jereshia Hawk’s services and strategies, visit https://www.jereshiahawk.com/.
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