Navigating the Valley of Despair in Business

The Valley of Despair is a term used to describe the emotional state that people experience when they're going through a period of extreme resistance to reaching a goal or a moment of significant change. This can bring up feelings of loss, shame, doubt, depression, and failure. And yes, despair. But it can also inspire profound insights and personal growth.

In this blog post, I’m going to chat about my own experience with the Valley of Despair, what I’m doing to navigate through it and the lessons I’ve learned in the depths of it.


This post is purely based on personal experience & opinion. I am not a licensed therapist, counsellor, or doctor. If you feel you require assistance or support with whatever you might be struggling with, please consult a professional.


The Highs Before the Valley

My creative business started innocently enough; A side gig that would allow me to flex my creative skills and bring my ideas to life outside of client work.

It never felt like work.

I’d spend evenings and weekends creating new designs and uploading them to print-on-demand sites without a blink of fatigue.

I saw multiple $20K (gross) months and continued to expand on designs and product lines. It felt like I was on my way and things could only get better.

After a time, I wanted a little more control over the quality of the product and a more personal customer experience. So, I started an Etsy shop and brought in my own inventory.

Greetings from Home postcard design

One thing led to another…

After 3 years of “side hustling”, in January of 2020, it became my full-time job.

I managed to work through the difficulty of the pandemic by designing & releasing Greetings from Home postcards which kept my business buzzing for months.

In the first year, which built off of my previous 3 years, I had created and fostered a business that had 7 streams of income which included e-commerce, in person markets, wholesale, print-on-demand, a distribution deal, licensing deals, and freelance work. With that, I saw multiple $20K (gross) months and continued to expand on designs and product lines. It felt like I was on my way and things could only get better.

I basked in the excitement knowing my efforts were paying off and I was making a living from my own creativity. To be able to be my own boss AND be the creative of my own company, felt empowering and a dream come true.

And it was, until things started to wobble.

Early Warning Signs of Trouble

The early warning signs of the Valley of Despair started with looking at my sales data.

During my busy season of 2022, my e-commerce sales numbers saw a bit of a dip. Wholesale sales followed some months later. And that’s when I knew something was afoot.

I waited it out and kept things as-is until I had more data. But I started to see these red flags weren’t going away. I talked about this in another blog post.

I did what I could to mitigate the impact by reducing some unnecessary expenses, continued creating in the hopes that I could invest in my business again soon. I also invested in programs and a coach that could help me find the holes in my processes, help me work a bit more efficiently, and help me relieve the burnout I just couldn’t shake.

That helped but not in the way I expected.

Entering the Valley of Despair

In my coaching, I had discovered that my burnout was a result of not being truly aligned with what I was truly great at or passionate about.

Numbers got worse.

I kept a sharp eye on the economic conditions, hoping for a soft landing.

I pulled back a little bit more to ensure I could get through this moment in time as unscathed as I could. I reduced expenses, cut back on programs and coaching, and didn’t invest in new designs or product lines. All of my pursuits came to a halt.

During this time, I was also faced with a change that came up (surprisingly) in my coaching sessions; Moving away from products to offer services instead.

In my coaching sessions, I had discovered that my burnout was a result of not being aligned with what I was truly great at or passionate about offering. I also had taken on too much and my general approach to the business I had built, was faulty.

This rattled me for some months ahead of “The Valley” as I processed and wrestled with this truth. I sunk into a Dark Night of the Soul moving through periods of grief & confusion. Questioning who I was. What I had to offer through my art. What value do I bring (and want to bring) to my clients. And, would anyone care; Was I good enough, unique enough, skilled enough? Questions beget more questions here.

After finally accepting a new direction in my business, I started discontinuing product lines. But, products weren’t selling much at this time.

Even still, I kept in touch with clients and continued to look for opportunity. Fulfilled orders that did trickle in (thank you!) and refocused on personal projects to build up my freelance illustration, graphic design, and tarot clientele.

Yes, tarot readings.

Tarot was a practice I explored as a teen and picked up again in early 2023 as a means of research (for my own oracle deck creation) and to reconnect with my spirituality as I navigated difficulty in my business. I also wanted to use this knowledge and skill to help others moving through challenging times as well. So I started a tarot reading YouTube channel and read tarot at a local metaphysical shop to help bring in some extra cash.

However, at this point the economy seemed to be in a full on recession and things got a little worse for my product business.

The depths of the Valley of Despair [TRIGGER WARNING]

You’re not alone. I’m here with you.

Sales had reduced in my busiest months by a whopping 75-80%. Instead of $20K (gross) income per month, I was making around $3-5K per month, which didn’t leave much after fees, taxes, office supplies, inventory reorders, and bill payments.

After spending the business savings cushion I had, the debt started to increase so I could support my personal and business expenses.

I knew this wasn’t sustainable so I ramped up my efforts to sell. To refine. To connect. To foster. To find as many ways to use my skillset to earn money. Even applying to other unrelated jobs that would offer some financial security during this time.

All efforts were falling flat.

I still showed up each day with great hope that there’d be a few new orders. An opportunity to collaborate. A job offer. Something! But most days started and ended without much to write home about.

I felt lost.

My hope started to fade and I started showing up with very little enthusiasm and motivation. I had lost my sense of purpose. Everything felt pointless. Insignificant. I felt useless and worthless.

There would be days I’d spend in an emotional and mental hole having these thoughts overpower my will to create and even care for my physical body. I cried with every private moment I could find; In my car at the grocery store. In the shower. At my desk. Cried myself to sleep or during meditation.

I asked what it’s all for and why should I bother continuing. Would anyone care if I fell off the face of the Earth?

It got very dark.

This somewhat reminded me of my Dark Night of the Soul experience. But this felt like it was on a whole new level. Or maybe it was just a continuation.

Either way, I didn’t recognize, nor like, this person I was seemingly “becoming”. Someone who couldn’t overcome this challenge. Someone who felt so negative and hopeless. Someone who no longer felt “in love” with my business or connected to my creative purpose.

A far cry from the ambitious, prideful, optimistic soul that started my business. Where did she go? This brought up alot of subconscious beliefs and feelings from the past. Little did I realize this Valley entailed much more than a business shift. It also was a space for personal healing.

One thing I did get right though, I couldn’t continue like I had been so I had to find a different way, a healthier way, of processing it.

Finding Strength in the Valley of Despair

I found ways to find comfort and stepped out of the fray for a moment. Even when I didn’t believe it would help.

I doubled-down on my spiritual practices.

Ramped up my meditations. Took part in more at-home yoga. Spoke with a good friend and my spouse about my struggles. Found free resources online.

I found ways to find comfort and stepped out of the fray for a moment. Even when I didn’t believe it would help. Or when I wanted to take action. Or when I just wanted to lump up in the corner and disappear.

However, some days, I even got frustrated with all of that. With trying to lift myself up and create change for myself. It just felt too heavy and hard.

There were moments I got angry. Frustrated. Where I wanted to sell everything off at steep discounts, quit design and illustration all together, and completely say goodbye to my dream. Fuck it. The scary part was I got to a point where that felt ok. I was good with that being the final resting point. I was so done.

What else could I do when I feel like I’ve done it all?

One thing I had yet to try was full and complete surrender. What if I simply let it all go? To let it fail, fall, crumble. And to fully allow what was next rather than force what I think things should look like?

I had a such a stranglehold on trying to control the external and came to realize the resistance and the need to fix / improve this experience, even deny my not-so-great feelings, was possibly the reason for my continual suffering and blockage to moving forward. What was I not seeing because I was so fixated on keeping Jack in the box?

With that, I eventually got to a point of radical acceptance.

  • I started to release the pressure of the “should’s” and expectations I put on myself.

  • I gave myself permission to not achieve. To be “lazy” and unmotivated. To just, be.

  • I gave myself permission to not have hope or expectation. But to accept whatever the day brought.

  • I gave myself permission to feel what I needed to feel when I felt it and nurtured the emotion that came up.

    • If I felt sad, I cried and asked “What do you need? What would you like to share with me?” It’s ok dear one, I hear you and see you. Let it out.

    • If I felt unmotivated, I gave in and focused on other work rather than force myself to be creative.

    • If I felt tired, I napped.

    • If I felt anxious or depressed, I worked out. Or curled up in bed to simply, rest.

    • If I felt insecure, I would apply for jobs or do cold outreach to potential clients.

    • If I felt any hints of guilt, shame, or self-judgement, I pushed back and protected myself from that inner critic.

  • I leaned into what offered me comfort and joy, releasing the idea I had to be productive or sell it in someway.

  • I pulled back from social media. Stopped reading articles. Learning. Strategizing. Trying to find answers.

  • I noted my accomplishments in the last decade and reminded myself that my successes have been no accident. They are a result of my hard work, dedication, skill, and creativity.

  • I affirmed that if I can achieve before, I can and will achieve again.

  • I radically accepted, and met, myself (and my business) where I was at.

  • I came to understand alot was changing. A lot was out of my control and focused on what I could control vs. what I couldn’t.

Full surrender has been the most difficult part of this process. And I speak about this experience in past tense (as, one day it will be) but it’s still very much an experience I’m still moving through.

As an ambitious creative, I’ve prided myself on achievement. On overcoming challenges. Seeing results from my efforts. Feeling so much in control of my destiny. And now…feeling so helpless. Lost. Confused. Unmotivated. To the point, I’ve completely taken my hands off the wheel.

Where was I? Who was I? I’m going against everything I’ve known for so long.

But something interesting started to happen when I did.

Emerging from the Valley of Despair

I’ve allowed it to shape me rather than define me. To prepare me for the next chapter, rather than hold me hostage to an old story. To open me up to what is, what isn’t, and what could be.

While I’m not fully out of the valley yet, I’m starting to see some shifts within myself and my perspective that is atleast helping.

I’m starting to feel more neutral & extremely present.

I have no attachment to a specific outcome or have any expectation of what my day should look like. Even what my business should look like. Curiosity has taken over my fear.

I have my good days but still cycle through darker days. However, I don’t attach myself to them or make them “mean” anything other than a moment. I celebrate my good moments and accept the darkness, allowing what needs to flow in that moment. But I don’t expect either to stay for too long.

Whenever I feel an extreme feeling or emotion, I ask it what it needs or wants to say. I listen, allow, feel, and let go. I then start moving to the center point of that polarity to neutralize that emotional state. This seems to lessen the impact these emotions have on me over the long-term.

I’m so much more present than I was. I’m moving through the day one minute at a time. No longer attaching myself to what was but also not living in the future.

And to be honest, I’m still not sure what that looks like yet.

I’m trying to be ok with that. But it’s tough when I’ve been a planner and a manifester all my life. What’s next? Only a vague idea right now.

Regardless, I trust and have more faith in myself. I do have hope for the future but I’m ok that I’m not beaming with it right now. Every day is a new chance for something to shift and to slowly move towards what I want or need. Even if the path is a bit foggy right now.

I’m allowing this place to shape me (and continue to do so) rather than define me. To prepare me for the next chapter, rather than hold me hostage to an old story. To open me up to what is, what isn’t, and what could be.

I have gratitude for the privilege of this experience, for not everyone can safely or comfortably navigate and emerge from this experience like some.

So I hope that this post offers some support for those struggling with it and to help you know you’re not alone. You’re not a failure. I’m here with you.

If you’re interested in learning more, from a professional, here is a resource to get you started.

Be gentle my dear friends.

Have any tips for getting through the Valley of Despair?

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