From Printers to People: How One Conversation Changed a Career

In a world where careers often unfold by default, I discovered my calling in financial planning for business owners during a simple lunch with my dad. 

That conversation sparked a career devoted to helping families, entrepreneurs, and business owners navigate money with purpose and clarity.

“I realized I needed to be doing something that had a more positive influence on the world than selling printers.” ~ Josh Ackerman, Certified Financial Planner™

The Spark That Started it All

My path into values-based financial planning began with dissatisfaction. 

I was working in corporate sales and realized I wanted to build something meaningful. My father, who had spent his career in financial services, reminded me that true fulfillment comes from helping others succeed.

By that Friday afternoon, I had closed one last deal and signed up for my first Certified Financial Planner course. What began as curiosity became a lifelong commitment to succession planning and long-term relationships with family-owned businesses.

Why Fit Matters More Than Sales

In financial services, chemistry and trust are everything. I’ve learned that if a client and I don’t connect, the best outcome is to part amicably.

“If you and I don’t connect, the worst thing I could do is convince you to work with me anyway.”

That belief has shaped how I approach every relationship at Context Financial. I focus on transparency, building trust, and ensuring my clients always feel understood.

Financial Planning is a Verb, Not a Product

For me, financial planning for entrepreneurs isn’t about selling a one-time plan. It’s about the ongoing planning process.

Building Trust Through Process

True planning evolves as life does. It requires ongoing communication and adaptation, especially during moments of change such as retirement, business succession, or family transitions.

Speaking Financial

I often say, “I speak financial.” My mission is to translate complex financial language into something everyone can understand.

According to the first-ever S&P Global FinLit Survey, only 57% of U.S. adults are financially literate, underscoring the need for this translation.

Two Mindsets: Scarcity and Abundance

I help clients identify their emotional relationship with money. 

By balancing fear and optimism, they learn to create both security and growth. This balance is one of the key ingredients in sustainable succession planning..

The Human Side of Numbers

I often tell people that financial planning for business owners is “the most liberal arts career ever created.” It blends math, psychology, and communication to help people align money with meaning.

As an educator at the University of Kentucky, I’ve had the privilege of helping shape the next generation of advisors through the Certified Financial Planner program. My teaching philosophy mirrors how I work with clients: relationships first, numbers second.

A recent CFP Board study found that 93% of advisors say their work provides personal fulfillment because it improves clients’ lives; a truth I embody daily.

Moving from Transaction to Transformation

What began as a career pivot from printers to people has grown into a mission to guide family business transitions and personal wealth planning with empathy, clarity, and trust.

Success, for me, isn’t measured in assets. It’s measured in confidence. My goal is simple: to help every client see the full picture of their financial future and prepare emotionally for what’s next.

If you’re a business owner thinking about your next chapter, start early. Begin by discussing your business exit strategy, goals, and life after the transition.

Ready to explore your next step? Contact us today.

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A slightly different format this week. I’ve been reading investment articles, and I thought I’d highlight the parts that interested me. Here is a striking chart from a great article I got from Blackrock. The important lesson here is that very few of our clients actually have the classic 60/40 portfolio. And this chart kind of explains why.  With interest rates down around zero for the next year or two, the yield on bonds isn’t going to be anything to brag about. Our Yield model, which would benefit greatly from 14% yield in Treasury bonds, is heavy in dividend paying stocks.

There is still a place for bonds in the portfolio. They are a useful “insurance policy” when the market gets flustered.

This is a blog I’ve wanted to have for a while now. The chart above shows average returns for various asset classes over a period of time. As you can see, the longer the time frame, the smaller the columns get. This means the range of returns narrows.

Here’s where it matters to us. Part of our job is helping clients make decisions about how to invest their money in order to reach their goals. An early conversation about investing will often include a discussion about “the market” and the potential direction of a particular part of that market. This conversation is heavily influenced by the left side of the chart. That’s where the financial press finds stories. If there is volatility in the returns, that means there may be a way to turn that into a story, “Stock A has unexpectedly gone down, or up. Stock B has done the opposite!” That’s where the drama comes from.

The Story

Charles and Lisa had been clients for years. We had an exemplary advisor/client relationship: open, clear, and regular communication, and mutual trust. We had long maintained a plan that everyone had confidence in when we suggested taking part in a new exercise.  

As trusted stewards of others’ money, we prioritize regularly participating in professional development opportunities. We had recently completed a refresher on the Financial Life Planning program. Our relationship with Charles and Lisa pre-dated this approach, so although we felt we knew them thoroughly, we knew that going back to basics could only strengthen their financial plan. They agreed.

Handing down the family farm is about more than transferring assets—it’s about protecting a legacy, honoring hard work, and keeping the land in the family for generations to come.

But let’s be honest: planning that handoff can feel overwhelming.

Who takes over? How do you keep things fair without creating tension? What if no one in the family wants to run the farm? These are real questions that deserve thoughtful answers.

Here’s how to start making sense of it all.

It’s Not Just a Business—It’s Personal

When a family business is passed on, emotions always come into play. That’s especially true with a farm. The land holds memories. The work is personal. And for many families, the idea of “just selling it” feels like letting go of a piece of their identity.

So when it comes time to plan the transition, it’s not just about who gets what. It’s about how you make those decisions—and how you talk about them.

Fair Doesn’t Always Mean Equal

One of the most common challenges in family transitions? Trying to split everything equally among children who played very different roles in the business.

Estate planning expert Justin Schumacher puts it simply:

“Equal isn’t always fair.”

If one child has been working on the farm for years and another hasn’t been involved at all, should they really receive the same share? Giving each child exactly the same piece of the pie might seem like the easiest route, but it can cause long-term tension—or even risk the business itself.

Instead, focus on fairness:

• Who has been active in the business?

• Who wants to keep it going?

• Who would rather receive value in other ways?

Answering these questions—openly and honestly—helps set clearer expectations and avoid future conflict.

3 Simple Steps for a Smoother Transition

If you’re beginning to think about passing down the farm, here are three steps to help things go more smoothly:

1. Get Clear on Everyone’s Role
Take stock of who’s involved in the day-to-day work—and who isn’t. This helps shape your transition plan based on actual involvement, not assumptions.

2. Talk About It Early and Often
Don’t wait until a crisis forces the conversation. Sit down with your family, share your intentions, and invite feedback. When people feel heard, they’re more likely to understand—even if they don’t agree.

3. Bring in Outside Help
Sometimes, having an outside advisor in the room makes all the difference. They can offer objective guidance, keep things from getting too emotional, and help you think through scenarios you may not have considered.

What If No One in the Family Wants to Take Over?

It happens more often than you think. Farming is hard work, and not every child wants to continue it. If no one in the family is interested, you still have good options.

Local buyers are often eager to expand, especially those with operations already nearby. Working with professionals to value the farm and prepare for a sale can help you get a fair deal—and feel good about how the legacy moves forward.

Closing Thoughts: Protect the Legacy Without Creating Conflict

There’s no one-size-fits-all approach to handing down a family farm. Every family is different. Every business is different. But the goal is the same: to make decisions that honor your life’s work and protect relationships in the process.

With a little planning—and a lot of communication—you can set the stage for a smooth transition that respects both the business and the people behind it.

Want more insights like this? Check out the episode “Smart Strategies for Passing Down the Family Farm” with Justin Schuhmacher for deeper perspective and practical tips.

Thinking About Selling Your Business? Start Here.

Selling your business is a big deal.

You’ve put in the time, effort, and energy to build something from the ground up. And now you’re thinking about stepping away. That decision can bring a mix of excitement, nerves, and a lot of questions.

But here’s what most business owners don’t hear enough: selling isn’t just about the numbers. It’s about making sure your personal goals, financial life, and emotional readiness all line up.

If you’re starting to think about an exit, these are the four areas you don’t want to skip:

1. Get Clear on What You Really Want

Before you talk to buyers or even think about a number, take a step back and ask yourself:

“What do I want this next chapter of life to look like?”

Maybe you’re ready to retire completely. Maybe you want to stay involved in some way. Or maybe you’re looking for the time and space to start something new. Whatever it is, getting clear on your goals makes every other decision easier—from how to price the business to what kind of buyer you’re looking for.

We’ve seen too many owners get to the finish line and realize they weren’t ready to walk away. Being honest upfront helps you avoid regret later.

2. Clean Up the Financials

Buyers want clarity. They want to understand what they’re getting. That’s why organized, easy-to-read financials are such a big deal.

That includes standard income and expense reports—but also a clear breakdown of owner perks or discretionary spending.

When your books tell a clear story, buyers feel more confident. And that often means quicker deals with fewer surprises.

If it’s been a while since you cleaned things up, now’s the time to sit down with your CPA and go through everything.

3. Don’t Skip the Emotional Prep

This part often gets overlooked—but it matters just as much as the financial side.

Selling a business is emotional. You’ve likely tied part of your identity to the company. You’ve put years into it. So it’s completely normal to feel a bit uncertain—or even resistant—when the sale becomes real.

Take time to picture what life looks like after the sale. Who will you spend your time with? What will you do with your days? The clearer that picture gets, the more confident you’ll feel about making the leap.

And make sure you’ve got people in your corner—a trusted advisor, a CPA, or even a peer who’s been through it before. That support can make a big difference when things feel heavy.

4. Start Thinking Like a Buyer

What would you want to know if you were buying your business?

Buyers often come with questions about customer retention, recurring revenue, key employees, and future growth potential. The more proactive you can be in answering those questions—upfront—the smoother the process will go.

Show them what’s working, where there’s room to grow, and why your business is a smart investment.

Ready to Start the Conversation?

Selling your business isn’t just a transaction—it’s a life transition. And the better prepared you are on the front end, the more confident you’ll feel stepping into what comes next.

Start with your goals. Clean up the numbers. Be honest about how you’re feeling. And work with people who understand how to guide you through the process.

You’ve built something meaningful. When the time is right, you deserve to step away knowing you did it on your terms.

In the latest episode of Transition Talks, Josh Ackerman delves into what makes Context Financial uniquely equipped to handle the complexities of family business transitions. Founded by his father in 2000, Context Financial is built on the principle of understanding the client’s context before making recommendations. This episode reveals how this approach is particularly effective for family businesses facing significant ownership changes.

Context Financial’s Origins and Philosophy

Josh shares the origins of Context Financial, highlighting how his father’s vision emphasized the importance of context. This philosophy remains central to their approach, ensuring that each client’s unique story and needs are thoroughly understood before any financial advice is given. This foundational principle has shaped their success in guiding family businesses through transitions.

Our Focus on Family Businesses

Context Financial specializes in helping family businesses prepare for transitions, whether passing ownership to the next generation or selling to external buyers. These transitions are often complex and emotionally charged, involving family dynamics and long-standing business practices. By focusing on the specific context of each business, Context Financial provides tailored strategies that address both financial and relational aspects of the transition.

The Team and Their Approach

Josh introduces his team, whose dedication and problem-solving skills are crucial to their client-focused approach. He emphasizes the importance of finding team members who prioritize the client’s goals and demonstrate a genuine commitment to resolving issues. This ethos ensures that clients receive personalized and effective support throughout their transition process.

Building Trust from the First Meeting

The first meeting with Josh Ackerman is designed to be a no-pressure, exploratory conversation. Josh explains that this initial interaction is about understanding the client’s needs and determining if there’s a mutual fit. By focusing on building trust and understanding client goals from the outset, Context Financial lays the groundwork for a successful advisory relationship.

Why Context Matters

One of the key takeaways from this episode is the importance of context in financial planning and exit strategies, especially for family businesses. Understanding the history, dynamics, and goals of a family business allows Josh to provide insights and strategies that are truly aligned with the client’s best interests. This approach not only addresses financial concerns but also helps navigate the emotional and relational challenges that come with business transitions.

Conclusion

This episode of Transition Talks underscores why Context Financial is uniquely positioned to support family businesses through transitions. Their commitment to understanding each client’s unique context and building trust from the first meeting sets them apart in the financial advisory field. Whether you’re considering passing your business to the next generation or exploring a sale, Context Financial offers the expertise and personalized approach needed to navigate these significant changes successfully.

For more information or to schedule an initial consultation or to reach out to Josh and his team directly, visit Context Financial.

Listen on your favorite podcast platform: https://bit.ly/TT_Ep2 

Watch on our YouTube channel: https://youtu.be/saGMPTm_A-I 

In this episode of Transition Talks, Josh Ackerman shares the stories and experiences that inspired him to work with business owners navigating significant transitions. These tales illustrate the challenges and unexpected hurdles that arise when preparing for a business transition and underscore the importance of asking the right questions early in the process.

The Importance of Asking the Right Questions

Josh emphasizes the crucial questions business owners often overlook before making irreversible decisions. In a story where two business partners were ready to sell their business but hadn’t considered whether the sale proceeds would sustain their current lifestyle, Josh shares, “I realized there were questions nobody was asking these business owners before they made transactions they couldn’t take back.

The Identity Challenge

Many business owners, particularly those who have spent decades building their businesses, find their identity deeply intertwined with their work. It’s crucial to contemplate who you will be once you are no longer the boss. Josh highlights the importance of exploring this aspect, focusing on the questions that need to be asked before making irreversible decisions.

A Crucial Realization

Josh recounts a story about two partners preparing to sell their business. Despite receiving a seemingly good offer, a critical question about their post-sale financial stability revealed that the proceeds wouldn’t sustain their current lifestyle. This insight, stemming from Josh’s thorough understanding of their financials, helped them rethink their decision, leading to a more strategic approach to saving and growing the business value before eventually selling it successfully.

Planning for Retirement: The Personal Impact

A former client’s retirement journey highlighted the personal adjustments required post-sale. After selling the business and completing an earn-out period, the client faced a new reality where his wife had an established social life that he was not part of. This story emphasizes the need for business owners to consider their personal lives and relationships when planning for retirement.

Aligning Values with Capital

Josh stresses the importance of aligning one’s capital – time, attention, and money – with personal values. He notes that the hardest part isn’t the financial planning but rather defining what you truly want in retirement. Insights from his mentor about this alignment advocate for purposeful and values-driven planning.

The Family Business Transition

Discussing a family business scenario, Josh illustrates the complications that arise when the business isn’t large enough to support both the retiring owner and the next generation. This underscores the need for early and thorough conversations about financial expectations and realities when planning generational transitions.

The Role of a Financial Advisor

It’s important to have someone on your side who focuses on your best interests, asking critical questions that others might overlook. Josh and his team at Context Financial take this proactive approach, ensuring that clients are not only financially prepared but also personally ready for life after selling their business.

How to Connect with Josh

If you’re considering a business transition and seeking guidance, reach out via Context Financial. Start with a no-pressure conversation to explore how Josh and his team can assist in aligning business transactions with personal goals.

Follow the podcast for updates on new episodes. If you find this podcast useful, share it with others who might benefit from these insightful discussions.

Listen on your favorite podcast platform: https://bit.ly/TT_Ep3 

Watch on our YouTube channel: https://youtu.be/nPXb89mWhR8 

Have you ever thought about what truly matters to you beyond just the numbers in your bank account? Today’s episode explores a groundbreaking concept: the True Wealth process. Josh Ackerman explains how this innovative approach emphasizes the importance of aligning your financial strategies with your personal goals and values, ensuring a fulfilling transition into the next chapter of your life. Read on to learn about how this process can transform your financial planning journey.

The True Wealth Process

Traditional financial planning often zeroes in on the numbers – how much you’ve saved, invested, and earned. But as Josh Ackerman explains, the true wealth process digs deeper, urging us to ask not just how much money we have but what our financial resources are truly for. Money Quotient has pioneered a movement known as financial life planning. This method helps clients articulate and clarify their values and visions, making it more than just about financial gains.

Clearly Defining Your Goals

Understanding and expressing your goals is harder than it may seem. Many people initially think they know what they want, but it often takes introspection to uncover deeper aspirations. Josh emphasizes the real power of the planning process is in helping the client clarify and articulate these are the things that matter the most. Context Financial’s True Wealth process is designed to facilitate and enhance this understanding, guiding clients through tailored exercises and conversations that lead to aha moments about their life goals.

A Detailed Five-Stage Planning Process

Context Financial employs a comprehensive five-step process designed to cater to individual needs and life stages.

1. Explore: The initial meeting focuses on understanding your immediate needs and ensuring a good fit. Josh likens this to solving an immediate problem while looking at longer-term goals.
2. Engage: This stage delves into your money stories and perspectives, often revealing deep-seated values and priorities.
3. Envision: Here, you create a vision of your ideal life. “What are the things that if you didn’t get a chance to do this, you’d be really disappointed?” Josh asks. This conversation integrates both emotional and financial elements.
4. Enlighten: You gain clarity on how your financial resources can support your envisioned life, incorporating any shortfalls or necessary adjustments.
5. Empower: The final step involves ongoing monitoring and adjusting plans as needed, ensuring that you remain on track with their evolving goals.

Transforming your life’s financial approach starts with understanding what true wealth means to you. Josh Ackerman and Context Financial guide clients through a meticulously structured process that emphasizes personal values and goals over mere numbers. To learn more about Context Financial’s five stages of the Money Quotient True Wealth Planning Process, listen to this week’s episode.

Listen on your favorite podcast platform: https://bit.ly/TTep04 

Watch on our YouTube channel: https://youtu.be/8kSSLannVu0 

Have you ever thought about what truly matters to you beyond just the numbers in your bank account? Today’s episode explores a groundbreaking concept: the True Wealth process. Josh Ackerman explains how this innovative approach emphasizes the importance of aligning your financial strategies with your personal goals and values, ensuring a fulfilling transition into the next chapter of your life. Read on to learn about how this process can transform your financial planning journey.

The True Wealth Process

Traditional financial planning often zeroes in on the numbers – how much you’ve saved, invested, and earned. But as Josh Ackerman explains, the true wealth process digs deeper, urging us to ask not just how much money we have but what our financial resources are truly for. Money Quotient has pioneered a movement known as financial life planning. This method helps clients articulate and clarify their values and visions, making it more than just about financial gains.

Clearly Defining Your Goals

Understanding and expressing your goals is harder than it may seem. Many people initially think they know what they want, but it often takes introspection to uncover deeper aspirations. Josh emphasizes the real power of the planning process is in helping the client clarify and articulate these are the things that matter the most. Context Financial’s True Wealth process is designed to facilitate and enhance this understanding, guiding clients through tailored exercises and conversations that lead to aha moments about their life goals.

A Detailed Five-Stage Planning Process

Context Financial employs a comprehensive five-step process designed to cater to individual needs and life stages.

1. Explore: The initial meeting focuses on understanding your immediate needs and ensuring a good fit. Josh likens this to solving an immediate problem while looking at longer-term goals.
2. Engage: This stage delves into your money stories and perspectives, often revealing deep-seated values and priorities.
3. Envision: Here, you create a vision of your ideal life. “What are the things that if you didn’t get a chance to do this, you’d be really disappointed?” Josh asks. This conversation integrates both emotional and financial elements.
4. Enlighten: You gain clarity on how your financial resources can support your envisioned life, incorporating any shortfalls or necessary adjustments.
5. Empower: The final step involves ongoing monitoring and adjusting plans as needed, ensuring that you remain on track with their evolving goals.

Transforming your life’s financial approach starts with understanding what true wealth means to you. Josh Ackerman and Context Financial guide clients through a meticulously structured process that emphasizes personal values and goals over mere numbers. To learn more about Context Financial’s five stages of the Money Quotient True Wealth Planning Process, listen to this week’s episode.

Listen on your favorite podcast platform: https://bit.ly/TTep04 

Watch on our YouTube channel: https://youtu.be/8kSSLannVu0