From Hedgerows to High Growth: Turning Obstacles into Your Strategic Advantage
When the Path Suddenly Changes
Unexpected obstacles are a certainty in leadership and life. The real question isn’t if they’ll appear, it’s how you’ll respond. Will you leap over them, run around them, blast through them, or pause to form a committee? Will you hand them off to your team, or simply hope they vanish on their own?
I’ve even spent late nights at a coffee shop, working until closing time to push past challenges. But here’s the truth: obstacles rarely disappear on their own.
On D-Day, the Allied forces stormed the beaches of Normandy and secured a foothold in France. Victory seemed within reach, until the very next day, when they encountered the hedgerows. These thick, earthen walls had been part of the French countryside for centuries, but despite nearly a year of planning for the invasion, they had surprisingly gone unaccounted for. For the Sherman tanks, they were nearly impossible to cross.
Yet the Allies didn’t quit. Their mission was clear: liberation, freedom, and the survival of their brothers in arms. They adapted, developed new tactics, and pressed forward. Because they refused to let an obstacle define the outcome, history was changed.
All of the Above
In both my personal life and my business career, I’ve tried nearly every approach to overcoming obstacles. Lately, that’s meant more late nights at the local coffee shop, tackling extra tasks, and earlier mornings to make sure I still get my workout in.
Right now, I’m in the sixth year of 40 Strategy and the second year of 40 Accounting. We’re not just aiming for incremental growth, we’re preparing for a quantum leap forward. And at nearly every stage, that means facing new challenges head-on.
Obstacles have appeared in the form of evaluating our people, processes, systems, and partners. Some have been expected, others less so.
Take our upcoming 40 Strategy Growth Workshop™, our very first, happening in Phoenix on November 3 and 4. Securing the speakers was faster than I ever imagined, we quickly assembled an exceptional lineup. Now, the focus has shifted to filling the seats so we can help more leaders strengthen their own people, processes, and systems, and position their businesses for the next level.
But one workshop isn’t the end goal. We’re aiming for ten workshops per year, impacting 400 business owners annually. In each session, we’ll build tailored strategic plans to help participants scale their businesses and increase the value they can extract from them. We connect them in one-on-one sessions with experts to solve their specific challenges.
That requires a new skill set: selling to people we haven’t yet met. So, I’m investing in the best talent, people who can elevate our marketing, strengthen our outbound sales, and create a workshop experience that delivers for businesses from $400K to $40M in revenue. My vision is to have these events booked six months to a year in advance, with sessions hosted in destination cities across the country.
More importantly, I am dedicated to helping thousands of businesses win in the most competitive environment that they will ever experience, 40 business owners at a time.
Meanwhile, at 40 Accounting, growth is moving so quickly that we’re already hiring a new CPA tax accountant. We’re searching for someone who isn’t just highly skilled but also carries an entrepreneurial mindset, someone who will grow with us while delivering exceptional value to our clients.
Key Takeaways for Leaders Facing Obstacles
Clarify the mission. A clear purpose fuels determination when the plan changes.
Adapt quickly. The faster you adjust, the less momentum you lose.
Invent solutions. Sometimes you can’t force a problem to fit old methods, you need new ones.
Stay committed to the outcome. Persistence is often the deciding factor in success.
Draw strength from your team. Unity in purpose transforms pressure into progress.
Your “hedgerows” might not be made of dirt and brush, but how you face them could define your leadership legacy.
(….end)
Jason Sherwood, Founder & Creative Director, Phase 23
40 Strategy Growth Workshop - Nov 2nd & 3rd - Phoenix,AZ
Jason Sherwood is the founder and creative director of Phase 23, a branding and design studio that specializes in strategic brand development, interactive design, and packaging. With deep experience across both global brands and scrappy startups, Jason is known for helping courageous companies build bold, resonant, and impactful identities that stand the test of time.
A seasoned creative and entrepreneur, Jason combines the strategic discipline of brand architecture with the emotional intelligence of storytelling. He previously co-founded a consumer product startup where he developed the brand from the ground up, an experience that shaped his empathetic and practical approach to working with early-stage companies. He understands firsthand the tension between founder identity and company voice, and he helps business owners clarify that distinction while creating a brand that truly connects with customers.
Jason’s philosophy is that branding goes far beyond logos or color palettes. It’s about crafting a consistent experience, aligning internal culture with external perception, and building long-term trust with the right audience. His work is grounded in strategy, rooted in archetypes and audience psychology, and built to scale. Whether guiding clients through customer personas or brand positioning, he ensures their visual and verbal identity reflects who they are and how they want to grow.
In addition to leading Phase 23, Jason is a sought-after speaker on brand strategy and customer resonance. He has worked with renowned names like Nike and Brand Jordan, and he brings that same level of thoughtfulness to emerging businesses looking to find their voice and scale their impact.
Interested in connecting with experts and high achievers like yourself?
Reply or email kyle.pfeiffer@40accounting.com
Breaking Down the One Big Beautiful Bill Act - One Week at a Time
Tax Tip of the Week
Speaking of being innovative, the One Big Beautiful Bill Act, finally reinstates the full immediate expensing of U.S. R&D costs (Section 174A), allowing businesses to fully deduct domestic research expenses in the year incurred, and even amend prior-year returns for small businesses to claim catch-up deductions, greatly improving cash flow for innovators.
This is great news; but there is also some complexity to file these returns. If you are interested in connecting with one of our R&D tax credit partners, let us know.
Stay tuned each Saturday for more strategies breaking down the One Big Beautiful Bill Act, one topic at a time.
Contact us at accounting@40accounting.com or your local tax preparer, if you have any questions.
- Wake up 5AM during the weekdays
- Started walks up to 15 minutes through Friday
- 5 thank you notes
- No carbs till noon
- Bonus: Tracking at 308 push-ups per day (been increasing starting at 1 since last December)
