Eileen Wiediger of Steep Road: “You can’t have your cake and eat it too”

You can’t have your cake and eat it too. I really wanted to keep hanging onto that security blanket of predictability and stability. I would tell myself that if I only worked three days a week or two at my previous job, I could have it all. I could have security AND I could still […]

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You can’t have your cake and eat it too. I really wanted to keep hanging onto that security blanket of predictability and stability. I would tell myself that if I only worked three days a week or two at my previous job, I could have it all. I could have security AND I could still have plenty of time to create what I wanted to create. The reality is that didn’t work for me. Even when I was working part-time, my emotional and mental bandwidth was maxed out on my day job; leaving little time and energy to focus on those projects that meant the most to me.


Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Eileen Wiediger. Eileen has spent over 30 years in the Public Sector, focusing on creating high impact and engaging learning experiences. She is now a coach and consultant, pursuing purposeful and intentional work in the “passion economy.” Her soon-to-launch online community “solveation” is focused on creating learning experiences, coaching (both individual and group) opportunities, and fostering connection in service of helping women discover solutions to challenges and step into living their biggest and best lives.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I always say childhood was my first and most profound experience in negative motivation: it showed me who I didn’t want to be and how I didn’t want to live. As an adult, I experienced many fits and starts, both professionally and personally; and while they were painful, I now look at them as my attempts to “try on” who I wanted to be in the world. Despite the many protective mechanisms at play when I was growing up, there were also passions, which have endured such as a deep appreciation for beauty and excellence, a love of learning, and a deep-seated belief in the wholeness and resourcefulness inherent in each of us.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

There are so many! I don’t have a perpetual favorite because my life lesson quotes tend to change according to where I am in life at any given point in time. One that is particularly resonating with me right now is from theoretical physicist Max Planck: “When you change the way you look at things, the things you look at change.” I don’t think I realized how much my worldview and perspective had been shaped — one might even say “warped” to some extent — by my many years working in the public sector. Stepping out of that environment was akin to Dorothy’s tornado-based transition from black and white Kansas to the radiantly Technicolor world of Oz. My many years of professional routine had lulled me into a kind of auto-pilot mode both in what I saw and what I did. Moving into a new space and place in my life has opened my eyes to possibilities I’d never even dreamed of, which challenge me to do things that are new and, frankly, a little scary at times.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

What’s interesting about this question is the three qualities helping me move forward in my Second Chapter are the same ones that have stood me in good stead professionally for over 30 years; but I’d never really used these qualities in service of creating what I want — they were primarily used in helping others create what they wanted. Envisioning possibilities: Even working in a hierarchical organization entrenched in the mindset of “we do it this way because we’ve always done it this way,” I have always been able to see other possibilities and perspectives. Being able to see possibilities beyond present circumstances and limitations is also key to me finding a whole new way of being and living in this Second Chapter. Finding solutions: I like figuring things out, finding ways to fix or improve situations that aren’t working — it’s incredibly satisfying! One of my favorite problem-solving stories comes from a long ago experience working as a catering manager in a private hotel. We were hosting an elaborate bat mitzvah celebration for a very demanding client, which included a beautifully frosted and decorated Torah cake to be cut at its culmination. Having checked to ensure the cake was flawlessly decorated with the correct pastel colors, I left the function room. To my horror, a few minutes later the client came running to me bitterly complaining that when the cake was cut, they discovered it was not their requested flavor of chocolate, but a white cake. I knew I could not produce a correctly flavored and beautifully decorated Torah cake. I also knew we had chocolate sheet cake that could be plated without a huge amount of effort. Recognizing my top problems were to defuse the situation, make the client’s experience positive, and rectify the situation with a reasonable solution I told the client we had been concerned about the aesthetics of a dark brown cake with all the beautifully pastel decorations and decided to make the cake white chocolate so as not to spoil the overall effect. Chocolate cake slices would be available, too. The client was happy and got more than she’d asked for. The banquet team was happy because the solution was manageable. And I was happy I’d come up with a solution that worked for all involved. Making connections: I tend to be one of those people who sees connections — whether those connections are concepts, people, ideas, or efforts. Although I often tend to be the type of person who prefers to go it alone, I am quick to see opportunities for amplifying my own and others’ thoughts through related concepts or like-minded others. Over the years, I’ve connected many people who would likely have never met without my interventions; connections that have led to long-standing professional and personal partnerships. I guess you could say I’m a sort of match-maker, sans the romance!

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

My very short-lived experience in hotel catering aside, most of my career has been spent in the public sector. Initially I worked in areas such as systems engineering and systems integration until finding my sweet spots in training, instructional design, and knowledge management. Whether it was being in the front of a classroom or developing the courseware for someone else to teach, I found it incredibly satisfying to be able to find ways to teach new concepts or improve performance through instruction. I remember when computer-based training (CBT) was still in its early days and how exciting it was to consider where this new type of training could be used, for what, and how to make it engaging and interactive within the limitations of the technology we had at the time. At heart, I am truly a closet organizer — everything in its place and a place for everything, so knowledge management was a natural fit for me. Learning how to organize information in the best ways possible to suit different purposes, different styles, and still make everything easily accessible was another way I was solving problems and making connections! Writing about these experiences now makes me a little bit nostalgic and I also recognize the time had come for me to move out of the organizational cocoon and break out into a more entrepreneurial role, unfettered by hierarchy and other people’s rules.

And how did you “reinvent yourself” in your Second Chapter?

I’d have to see my reinvention is still a work in progress! When COVID hit, I was unable go into the office for quite a few months. During that time there was some work I could do from home, but there was still down time. And it was during that down time I began to wonder about what else I could be doing. I had the luxury of time — something I’d never really experienced before — and I used that time to dabble, explore, take classes, read, and really think deeply about what I wanted to do. I began doing some coaching and instructional design consulting work outside of my day job — and I liked not only the work, but the sense of autonomy and freedom that came with it. When I ultimately went back to the office and started a new project, I chose not to give up the work I was doing independently. Balancing everything was somewhat challenging and I’d decided it was worth it — I wasn’t willing to let go of what I’d started to build, even though I hadn’t found a specific focus yet.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

Honestly? The Universe gave me a big old shove into what’s next. I’d been dancing around the idea of doing my own thing for several years, but that dancing was more like circling the drain. I never fully committed to the dream, just held onto it like a fantasy security blankie. My mantra was “I want to have my cake and eat it too,” meaning I wanted to hang onto the stability and security of my day job, while trying to forge my own way. No big surprise, it didn’t work. When I started my last project, I said to all and sundry: “This is my last project, after this I’m out.” What I did not anticipate, however, was the project being dismantled after only six months! I don’t think the Universe could have spoken more clearly!

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

I don’t know that I discovered a new skillset, it’s more that I’ve re-purposed my existing skillset and decided to turn those powers toward creating something that is exclusively and wholly of my own choosing. Working in the public sector for a long time, my identity and my skills were all meshed in this professional persona, whether it was that of an instructional systems designer or a collaboration and knowledge management expert. The barrier I had to overcome was realizing my powers worked outside of that organizational environment and could be used in service of my own dreams and passions.

How are things going with this new initiative? We would love to hear some specific examples or stories.

Did I mention my reinvention is a still a work in progress?! With that said, I’m starting to find a shape and form to who I want to be and what I want to focus on in this second chapter. Coaching is going to be a big part of my reinvention, specifically coaching individuals and groups who are in a place of transition and seeking guidance in moving from where they are to where they wish to be. I am creating a virtual community on MightyNetworks, solveation, whose focus is “solving for U to find the Y.” My vision is to bring experiences, resources, and opportunities dedicated to helping women re-connect to their authentic selves and offering tools and support for them to live their biggest and best lives. Two of my planned workshop offerings include: Yoga Nidra Meditation “Lab” — crafting a personal intention, regular meditation, and check in on progress/results/ benefits; Past Pretty — a multi-part workshop to help women see beyond what is in their mirrors and recognize their value is beyond beautiful. Co-working is another concept I’ll be exploring; two specifically are: “Wow, We’re Writing” — a dedicated day and time where women can come together virtually to support one another in their writing; and the “League of Superheroes” — a virtual “board of directors” where we will share triumphs, tribulations, questions; and offer encouragement, counsel, and support.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m blessed to have some incredibly supportive and caring people in my life. My husband, however, has been steadfast in his love, support, and faith in me — all of which serve to lift me up in times of doubt and energize me further when I find momentum. During a particularly difficult family situation, I remember telling him I was simply not up to the challenge ahead, that I couldn’t do it and he simply said, “You are up to it and you’re already doing it.” I’ve never forgotten that moment and it serves to anchor me when I become fearful, I know I’m capable of doing hard things.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I struggle with believing in myself on the daily! What has really helped me move beyond the barrier of this limiting belief is recognizing that my feelings of inadequacy or insecurity are not unique to me. Often when I’m struggling with whether I’m good enough, smart enough, or just enough; I feel isolated and alone in my experience. And each time I am brave enough to share this feeling with others, I learn how not unique or alone I am! I work with a woman for whom I have great admiration and respect, perhaps even a little hero worship. I am often her online virtual producer (handling the technical side of virtual workshops or meetings) and before a recent event she mentioned having the jitters. I was absolutely floored that this accomplished woman who I always saw as perfectly polished and poised could experience the same mundane jitters I did, just another reminder of how connected we all are in our human experience.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I am blessed with genuinely caring friends who make up a large part of my support system and they often know me better than I know myself. While my transition to something new happened more suddenly than I’d originally planned, it seemed like I was the only one surprised by it. So many of my initial fears were allayed because my friends were not only not surprised, but they were also entirely encouraging of this move into something new and different.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Working in the same environment for 30 years, I had gotten amazingly comfortable with the routine, the sameness, and the ability to be on auto-pilot. Shifting out of that and into something entirely different — in the middle of a global pandemic no less — was jarring, to say the least. I’ve received several offers to come back, several very tempting offers, and the first time that happened I felt an immediate sense of relief that I could just go back to the known, to being on auto-pilot. That relief was very short-lived, though. As much as I longed (and still long some days!) for the comfort of stability and predictability I could have by returning to my former job, I am unwilling to give up the sense of challenge and autonomy I have and the joy of creating what I want to create.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

  1. You can’t have your cake and eat it too. I really wanted to keep hanging onto that security blanket of predictability and stability. I would tell myself that if I only worked three days a week or two at my previous job, I could have it all. I could have security AND I could still have plenty of time to create what I wanted to create. The reality is that didn’t work for me. Even when I was working part-time, my emotional and mental bandwidth was maxed out on my day job; leaving little time and energy to focus on those projects that meant the most to me.
  2. No job or amount of money can give you a sense of safety and security, you must find it in yourself. For a long time, I believed if I could just make a certain amount of money, I would finally feel safe and secure. Then I would hit that number or position, realize I still didn’t feel safe or secure, and increase the number, or shoot for the next best position. I finally realized there is not an amount of money or level of position that can fill that safety and security gap, I have had to find it within myself.
  3. When you are aligned and working on what has meaning for you, your priorities will shift. What I need and what is important in my life is so different today than it was even three months ago. If I’d found 500.00 dollars three months ago, I probably would have used it for fabulous clothes. If I found 500.00 dollars today, fabulous clothes wouldn’t even enter my mind, I’d put it into some new technology or training to further the community I’m creating.
  4. Be clear in your asks of the Universe. I tend to ask a lot of the Universe, but it’s only recently that I’ve realized my intention and desire behind those asks needs to be crystal clear for the Universe to deliver! Asking while I was still straddling the fence, being neither fully committed to one thing or another; never really led to anything. I’ve noticed when I am super clear with myself — either in what I want or do not want — the Universe responds in kind. For example, when I turned down a former manager who’d asked me to come back; I got a new job with a new client within 24 hours.
  5. We are all connected in the experience of being human. Nothing I am experiencing is unique to me and I am not isolated in those experiences. When I hit a slump and start doubting myself, I also tend to feel incredibly alone and isolated in what I’m feeling. Realizing these feelings of inadequacy are NOT unique to me has given me the courage to be vulnerable with others and share my fears with others, which ultimately leads to a deep sense of connection and camaraderie.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would love to help women re-connect with their creativity and inner resourcefulness because I believe we cannot share the gifts we possess until we recognize their existence within. My greatest hope is the impact of my work is that in some small way it helps others to let their highest and best selves shine and show up.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂

Louise Penny, hands down. Louise Penny is the author of the Armand Gamache mysteries, a series of wonderfully rich and complex stories set in Quebec. With each new book, I love picking up the narrative of characters whom I’ve grown to love over the years — it almost has the feel of a reunion of sorts. Her books are neither cozy mysteries nor police procedurals but have some elements of both. Louise began her writing career somewhat later in life, something which gives me both energy and determination as I build my own second chapter. Meeting Louise for a conversation over café au laits and croissants would certainly be a peak experience for me!

How can our readers further follow your work online?

Solveation, my community, coaching, and learning experiences will be going live the on Mighty Networks platform in April 2021 and can be found at: community.solveation.com.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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