Paved walking trail through the woods with a wooden bridge in the distance

I’m a failure.

That’s what I told myself for months, years really. My business wasn’t growing, heck it was actually shrinking, and quickly. Nevermind the world was in a pandemic. Other businesses were able to quickly pivot. But not me. Not my business. Because I’m a failure.

Success seemed slippery, impossible even. I’d been designing and writing for financial clients for years, yet didn’t have a full client roster or a solid source for leads. The sheer number of workshops, courses, books, and podcasts on how to grow a service-based business I’d consumed surely should’ve helped. Was I not smart enough? Ambitious enough? Disciplined enough? What was wrong with me? I didn’t have those answers, but I knew, somewhere deep, there had to be a better way.

This all bubbled up August of 2021, the week after my birthday. I typically have bouts of introspection around transitions – the beginning of the year, an anniversary, a birthday – but this one felt so much deeper, and darker. And it’s funny, I made it through my 50th with flying colors. I LOVED that birthday, even though it was when we were really social distancing.

And that’s my typical M.O. Pollyanna should probably be my middle name. Call me Miss Mary Sunshine as I’m always looking for the silver lining. But here I was, a newly minted 51-year-old with spirals of low esteem, crying jags, and not knowing how to get out of the spinning negativity.

So why, or how, does someone so positive get so lost in negativity? Were the business results really that bad? I remember very distinct moments wondering: how do other business owners frame up their failures? Surely I’m not the only one feeling such a loss personally as my business tanked? How do they get through it?

I struggled to find any meaningful answers. Google searches just left me overwhelmed. Social media felt even more judgey – feeds full of “here’s how I earn $10,000 a month.” I tried reaching out to my Chamber connections and local business groups, but that just revealed a big gap in the support for the mental and emotional side of entrepreneurship.

So I’m aiming for that gap. I’m sharing my experience so maybe just one other person might get reassurance and validation: they are not alone in their self-employment or self-esteem struggles. In sharing this experience, I also hope to highlight possible directions to take in the search for a stronger self, which might mean reframing the very definition of success.

And now, a word of caution. This is an ongoing experience I’m sharing, one in which the end is just starting to materialize. But after years of hard work on my mental and emotional well-being, I am in a much better mental and emotional place. And I am so very, very grateful.

So how did I get here? Let’s go back to the messy downward spirals.

Ink smears

The month or so after my birthday was very messy indeed. Lots of damp, wadded tissues, lots of gravel in my shoes from walking the nearby greenway. Ink smears on my fingers from journaling as I worked on why my business was failing, why my spouse and family should even be proud of me, what meaning my life has had.

I had no answers for any of those questions, but wanted them desperately. If only I knew what I was meant to be doing, who I could be serving. If only I had some sort of deep passion for a topic or activity or cause. If only I could do something people would remember, be proud of, talk about in awe, then maybe my life would mean something. If only.

But there I was, not even able to get out of my own way. I knew wallowing in self-pity was making everything worse, yet I didn’t know how to right the ship.

Somehow the word “tools” came to mind. I needed tools to help me. Which led me to therapy. I don’t know why I didn’t think of it earlier. Seems kinda obvious now. But I do remember having this feeling that I ‘should’ be able to do this without therapy. My issues aren’t that bad. If only I could just get it together. Trouble was, I couldn’t get it together and each week that went by just compounded the issue.

I started with a counselor in October. I was ready and eager to get going, to move beyond being stuck. I came in with questions like “How can I create impact with my life? What will it take to bring in revenue, be successful with my business?”

And then she asked, “Well, what does ‘impact’ mean to you?”

Uhm, well, uhm.

“Do you REALLY have nothing to be proud of?”

Well, uhm.

These two questions alone took me deeper into my own motivations. I started seeing how the success I’d been seeking was based on traditional, external measures. I’d been looking for validation from others. I needed – wanted – to find my own sense of self-worth, my own measures of success.

She helped me start that journey with some excellent tools I still use today:

  • Spotting, then challenging & diverting negative self-talk
  • Identifying positive daily experiences
  • Recognizing my strengths
  • Exploring ways to use my strengths

Important note: These tools work for me. They may or may not work for you. I encourage you to find a counselor or therapist to help you build your own toolkit.

My toolkit has expanded since then. I came across guided meditation that fall which has been very helpful in keeping me grounded and centered. I also am more intentional about doing activities which give me energy. It’s taken some starts and stops to learn how to use those tools effectively both on the personal and business levels, but these tools and others have brought me closer to knowing my true self and my purpose.

So what about the business

As I wrestled with my mental and emotional well-being, I recognized running a business had a huge impact on this struggle. I really enjoyed the flexibility and many other benefits of being self-employed, but maybe it was time to give the business a rest so my well-being could get stronger.

I started scrolling through job boards, applying for positions. But even that just led to more doubts and uncertainty. What did I even WANT to be doing? How would companies view an applicant with five times more experience as the position required? I would apply for design positions, but then feel my portfolio of work wouldn’t hold up against younger, fresher applicants.

I kept thinking there’s got to be some intersection of my talents, skills, and expertise with an audience and/or a company which is in need of that trifecta. The job openings were not anywhere close to aligning with my situation. Even just trying to find SOMEthing which used my skills felt so fruitless. But apply I did. No requests for interviews, nothing.

Again, the feeling of being a failure crept back up: I can’t even get a job.

I felt myself getting sucked into those negative spirals again. This time though I pulled out my tools. I focused on my strengths, examined my motivations, including: was this job search process and then the work I’d be doing in line with my values? Was impressing the companies and their impersonal hiring system even worth my effort? Then I distinctly remember realizing: maybe I’ve been trying to impress the wrong people in other aspects. Or maybe, trying to impress ANYone is what I needed to challenge. What if the niche I’d been pursuing in my freelance business just wasn’t aligning with who I am at this phase in my life?

Finding my mode of operation

At this point, I’d been working with credit unions and community banks, both as an employee and then as a freelancer, for about 16 years. The work was interesting: I found it a challenge to design & write within such a tightly regulated industry. The work was recurring: there’s always a product or service to promote. And they were good clients from a business perspective: paying quickly, hardly any need for work outside of 9-5, federal holidays were quiet, and many other perks. But I found myself struggling to get new clients.

I tried playing the game. I went to industry conferences, travelled to association meetings, drove around the region to visit in-person. Wrote articles for industry publications. Submitted speaking proposals to those conferences & meetings. Heck, I even got accepted as a speaker at one of the national conferences! I was so excited and so confident THIS would turn my business around. Then two days before flying out to the conference, the world shut down. Yep. The conference was scheduled for March 2020. And when the pandemic brought a pause to in-person networking, I quickly realized I was getting overlooked by prospective clients. They were being woo’d by large agencies and people with aggressive sales techniques.

But maybe I didn’t want to be ‘playing a game.’ I was so very tired of trying to prove myself, of feeling like I had to coerce and persuade, to flatter and entice in order to get noticed by prospective clients. Do I even WANT this type of client if I have to be playing a game which doesn’t reflect my values?

The day I decided to stop pursuing financial clients a huge weight lifted off my shoulders. I had just finished up a video meeting with another credit union service provider. She had all the success markers: busy with business engagements & travel, speaking at events, respect of other providers, teaching at association ‘schools’, busy, busy, busy. So in my quest for getting more clients, I asked if she could provide her insight into how her clients were viewing the creative side of marketing – were the services I’m offering even in demand?  She was so gracious with her time and insights, including amazing behind-the-scenes info on her own process for prospecting. She was excited about the process – said it was hard work, but worth it. At first I was really excited to hear what was working and that I had some activities I could try. But as she went into details of the interactions and activities, all I could think about was how they went against my very nature. But maybe I just needed to buck up and ‘put in the work’? Step outside of my comfort zone? Get more disciplined or whatever? But did I? Really?

I decided then and there that those tactics might very well work for her, but she is not me. Her personality works great for those tactics. My personality is very different. For me to take on those tactics would be going against my grain, feel forced and fake. And no one wants to work with a fake.

So after that call, I made the decision to stop pursuing financial clients. After years of working in that industry I was pulling up camp and moving on. I didn’t know what was next, but I knew it wasn’t focusing on financial institution marketing.

I clearly remember removing that niche from my LinkedIn profile, then releasing this long-held breath. No more need to prove my value to those who have completely different values. Ahhh.

Is it me or is it my business? Is there a difference?

Coming to terms with how my mode of operation didn’t align with the financial industry’s mode of operation really helped me recognize some of my own values as a person, and as a business. And to start thinking: what is the line between me and my business? Is there even a separation if the business is essentially me? Does this business model of being a freelance/consultant/solopreneur have any sort of identity separation?

People hire those they know, like and trust, especially when it comes to services. So it really is no wonder I found it hard to remain objective about the reasons I may or may not be attracting prospects. My inner critic was screaming “hey there, don’t take it so personally”  yet I wasn’t sure how to separate the rejection which happens in the business world from being a rejection of me.

I went through some business coaching the first few months of 2022. We talked quite a bit about whether I really want to stay self-employed (yes). Then what I’d like to be doing as a self-employed person, which led me to a consider a pretty specific type of marketing service offering. As I was drafting up those offerings, I distinctly remember hearing an inner voice saying:

“Will this copy get them to like me?”

Wait. What?

“Will this copy get them to like me.”

Hearing that really caught me off guard. I realized then and there just how tightly integrated my own perception of me as a person was tied to how my business was accepted. Which then led to another realization: If people weren’t interested in my business, I took that as non-interest in me. No wonder I saw myself as failure when my business was in a down cycle.

Internal vs external

Since that revelation, I’ve been working hard on building internal love and acceptance while reducing my dependence on external affirmations. This journey has revealed just how extrinsic my motivations have been, things like seeking approval from others (prospects ‘liking’ me) and getting rewards for doing the work (e.g., if I don’t bring in revenue, I have no value). And studies show when we’re chasing extrinsic goals, we tend to be more stressed, less satisfied, and have higher anxiety.

One big moment in this journey of self-acceptance was tied in with social media. I was already aware of the dopamine side of social media – how our brains physically and positively respond to the interactions – but this other side of social really hit me when I took an unintentional digital break.

My husband and I were on a trip, renting a place so remote there was hardly any cell service. The first day I felt the pull to check social & FOMO kicked in hard. What was everyone doing? Where there any scandals, breaking news, viral memes I was missing? The second day I cared way less about checking – I was living more in my moments, enjoying the quiet, the scenery, the connection with my husband. Yes, the world was going on out there without me, but you know what? I was OK with that. More than OK actually. The third day I realized I cared way less about posting. I had been taking photos along the way, thinking of what I’d post when we got service, but then I just started taking photos for the joy of it – framing up a beautiful scene, capturing golden light or detailed textures. I didn’t care if anyone saw these or knew what I was doing. I didn’t need the likes to let me know I was having a ‘successful event.’ When this shift happened, I felt much more free to just do whatever I wanted to do. I didn’t feel the need to do something worth posting. I didn’t feel the need to perform. If I didn’t want to do a damn thing all day, so be it.

Bare feet resting on a boat's edge that's on a lake with forest shoreline in far distance

Not posting while I was on vacation – which is usually when most people are at their postiest – really showed me how much I felt the pull to be living a life worth attention. But that type of ‘success’ was actually getting in the way of me being happy and content. So when I felt actually felt MORE worthy, content, and at peace by not posting, I knew the markers to being ‘successful’ were not ‘out there’ but in me.

If I’m striving to have someone be in awe of me and my activities, I’m aiming for a moving, paper-thin target. What impresses someone today might be completely different tomorrow. They have their own perspective and agenda, one which colors their own sense of worth. If a friend or family member was raving about someone else’s vacation, business success, or even an exciting weekend activity, I used to wish I had some exciting activity or achievement they’d be proud of so I could be special in their eyes. I wanted to be worthy of being mentioned.

But now? What other people find exciting, buzz-worthy, or special is no longer my aim. Turns out my worth isn’t tied to what others think. Their “special” does not make me happy or successful.

So as I worked to escape the pull of these extrinsic motivations, I wanted to uncover what success does mean to me. What does bring me lasting joy? 

My meaningful momentum

I gained meaningful momentum in my journey when I got clear on my values and strengths. I then explored how I could use those in service to others in ways which felt more aligned with how I like to work.

My values are centered around kindness, love, positivity. My strengths and talents are centered around a love of learning, understanding the broader context, helping people see how awesome they are. 

 I also realized I was no longer satisfied with helping businesses grow. I felt pulled towards helping people grow. My work as a freelancer/consultant brought the most joy when I was in deep conversations with my clients, helping them plan, strategize and prep. I wanted more of those one-to-one interactions, developing relationships as we developed their work, project, job, career.

That’s when I thought leadership coaching might just be right up my alley. 

That very first coaching training course I took felt like such a risk. Quite a bit of money was invested without knowing how it would all pan out. But all of that was laid to rest during the first class.

As we all introduced ourselves and our reason for taking the course, I felt tears well up. My shoulders relaxed. My heart swelled. It was the first time in ages that I was in a group of people with similar values, stories, and the drive to make a positive difference! I found my people!

Then, as I learned about the coaching process, I was tickled to discover I’d be able to fully express a core part of my being – my insatiable curiosity! One of the key elements of effective coaching is asking powerful questions. Asking questions is absolutely second nature to me. I can’t help but ask questions and often have to tamp that curiosity down in certain social situations. Here was a profession that was begging me to use a strength I am driven to use!

And now, with almost a year of coaching under my belt, I’m thrilled to share just how ‘successful’ coaching makes me feel. Working with my clients to get them unstuck, to find their own meaningful momentum is such a joy. I am using my talents to help others in a way which aligns with my values and natural mode of operating.

Shifting success

Success is no longer about doing activities or having things which others might envy or find ‘special.’ Success to me, at this stage of my life, looks like being the best I can be so I can love and serve fully and freely. Success is being able to use my gifts in the service of others especially when values and principles are aligned.

This huge shift in my take on success has brought me such peace, joy and contentment.

Getting to this place has been a two year journey of self-reflection, studying and then putting those theories into practice.

I’m very grateful of the support from family, friends, and clients. Through so many moments of uncertainty and doubt they simply were just there, by my side, giving me space to explore and experiment.

Whether or not my coaching business will be ‘successful’ according to society’s definition is still a work in progress. There’s the return on investment for the trainings as well the ongoing costs of running a business which need to be covered. I may not ever reach levels of fame, prestige or power society recognizes as markers of success. But in my definition of success, I’m already there: I’m using my natural talents to serve others through ways which align with my values.

I now know: I am not a failure. My marketing business failings were a stone I stumbled upon in my journey to find my true self. I am curious, creative, positive, with an artist’s eye, a student’s mind, and a loving heart. I am of the Divine, a child of God and I will do my level best to encourage others on their journey of self-acceptance, even in the face of failure.