Burned or Disappointed by Past Business Investments? How to Heal, Discern, and Trust Again
“The LORD is close to the brokenhearted, saves those whose spirit is crushed.” (Psalm 34:19)
Have you been let down by a past investment, program, or coach? Perhaps one promised massive transformation but left you disappointed, shaken, in debt, or in more of a mess than you were before.
These unfortunate situations can leave big-hearted entrepreneurs afraid and guarded against future support, despite a seemingly great opportunity to fill a new need.
We all need support – we’re designed to work in collaboration with others and to be surrounded by community. God our Father tells us: “It is not good for man to be alone” (Genesis 2:18). But it is also really difficult to trust and discern the right kind of support when you're carrying the weight of a past failed investment or business relationship.
Compassion for the Guarded Heart
One woman vulnerably shared this with us during a discernment call:
“In full transparency, I actually had a huge business investment go really bad recently. It shook the foundation of my whole business and family life. It spilled into our finances. It felt like I was at a crossroads and knew it could either help me out of the hole I was in, or I’d have to shut everything down and pursue something different.”
If you’ve been in a program that promised to walk with you but left you feeling even more alone – or you were led to believe that it was your fault things weren’t working – that experience leaves a mark. It (very rightly) doesn’t just make you hesitate to invest again, it can cause you to question your own ability to discern effectively. These negative experiences can be especially troublesome if they result in financial uncertainty or internalized shame.
It’s difficult to trust again when you’ve been betrayed by someone you trusted to lead or were promised more than you received by an institution. It’s valid to feel guarded and wary and protective against “falling for that again.” It’s wise and healthy to slow down and give yourself guardrails for discernment before saying “yes” again - this is compassion.
When Trust Has Been Broken
When trust is broken – especially with someone you wanted to trust to lead and deliver – it shakes an internal foundation. This is especially true if you already felt vulnerable or uncertain when you made the decision.
You may feel a desire to pull back and put up walls, testing the boundaries of safety before you place your trust in yet another coach or consultant. You may experience feelings of tension, isolation, confusion, stuckness, judgment. Questions may run around in your mind, like:
What if it happens again?
How do I know if I can trust myself?
What kind of support is actually safe?
The great news is, these questions and emotions aren’t a problem – they’re a sign of wisdom.
Your Resistance Is Not the Problem
Your resistance to being “sold to” or pressured into a big commitment is actually healthy.
We are in a moment of reckoning with the manipulation and pressure tactics that have bombarded our psyches for decades through sales and marketing. Many of these tactics did not honor our humanity. Thankfully, more and more people are saying: that is not okay with me anymore.
So, consider this: What if your resistance and guardedness to a sale is not an example of you being stuck but evidence that the way you’ve been treated in the past is not okay? What if your hesitation is proof that you care deeply about what comes next? This is your permission to make a new commitment to listen to your intuition and to no longer sacrifice your peace or financial safety in the discernment process.
You don’t need to be talked out of your caution. You need someone to honor it.
You Deserve a Sales Process That Honors Your Humanity
This year, we are recognizing the need for longer discernment periods in potential client conversations. The sales process has lengthened. Maybe you've noticed this shift as well. People are taking more time before saying yes.
People need more space, and you likely do too. There’s a lot going on in the world right now and it is affecting many aspects of life and decision-making, including your nervous system’s tolerance for more input, invitations, calls to action, or even change itself.
If we want to conduct sales that honor the humanity of the person in front of us, then the goal shouldn’t be to convince or even to have the highest conversion rate possible. Instead let’s create a space where every human being feels free to pause, to pray, breathe, and get more clear on their root-level needs.
As coaches or consultants it is our responsibility to engage in a better process – one that holds space for discernment that is built on trust and relationship. The process is one in which each party is secure in the value and agency that each individual offers. It is one that doesn’t have us, the coaches, trying to “get” or acquire clients.
In our process, both parties can listen and explore the following questions together:
Does what we offer match what you need?
If so, how do we build something mutually beneficial and life-giving?
The coach, consultant, or sales person ought to be prepared to initiate a pause in the process, i.e. point out that it might not be the right time for the financial investment of coaching. Although it is uncomfortable to do so, there is a moral obligation that we are all called to in business.
Questions for Discernment
It’s vulnerable to invest in support, especially if you’re at the intersection of needing help to grow your income and needing income to get help with your business. The capacity struggles or exhaustion may be deeply affecting your quality of life, and that’s a tough “catch-22.”
Still, you don’t deserve to be pressured into investing in something that’s going to cause even more harm and strain. That’s not true accompaniment or goodwill.
What you do deserve is open conversation, trust, honesty, mutual discernment, and for your free will to be honored. That’s what lays the foundation for a relationship that can be truly beneficial for everyone involved.
If you’re in a place of discerning a coach, consultant, course, or program, here are some questions to slow down and prayerfully sit with:
Is this the support I need?
Is this the support I need right now?
What does Jesus have to say about it?
What has the cost been of waiting for support?
Is there a cost to continuing alone?
What’s happening inside me as I stay in patterns that feel heavy, unsustainable, or misaligned?
Am I being invited to try something different?
Mull these over with the Lord, and notice what you feel in your body. These questions are a place to begin. Don’t rush toward answers, but attune to what’s real and true inside of you, and have an open conversation with God.
A New Way Forward
You deserve support that makes you feel safe, not sold to.
You deserve discernment that feels spacious, not rushed.
You deserve leadership that builds trust, instead of eroding it.
If your heart still hurts from a past investment, know this: the story’s not over. Your caution is valid and there is another way.
You don’t have to do it alone, and you don’t have to override your gut.
You can discern and choose differently this time.
Megan Gephart is a Certified Director of Operations, professionally trained Mindset Coach, and Army Veteran who brings 12+ years of leadership in the military, public relations, entrepreneurship, and nonprofit sectors. Passionate about organizational change, she specializes in strategic planning, operations, leadership development and team growth as the Co-founder and Operational Strategist with Apostolic Fruit. Megan is a wife of an active-duty Army officer, and mother of three energetic boys.
Anna Saucier is an Embodied Leadership Coach and Sustainable Business Consultant, Certified Emotional Freedom Technique (EFT) Practitioner, and Certified Mindset Coach. As CEO and Co-founder of Apostolic Fruit, she leads a team that mentors leaders, organizations, and entrepreneurs in creating practical, root-level foundations for thriving and profitable fruit that lasts. Anna is a mama of two, minimalist, and lover of both bustling cities and silent stillness. She and her family live semi-nomadically around the world.