Marita Herkert-Oakland of Relumed: “Recognize Your Strengths and Weaknesses”

Recognize Your Strengths and Weaknesses: When thinking about the company we want to build, we start with our vision for what we want to build, but that is informed by our strengths. Creativity? Check! Supportive, compassionate client work? Check! By bringing together our superpowers, we can be confident that we are building the strongest company […]

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Recognize Your Strengths and Weaknesses: When thinking about the company we want to build, we start with our vision for what we want to build, but that is informed by our strengths. Creativity? Check! Supportive, compassionate client work? Check! By bringing together our superpowers, we can be confident that we are building the strongest company we are capable of.

Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Marita Herkert-Oakland, co-founder and lead facilitator of Relumed, an agency that offers visual thinking facilitation and workshops. She uses her background in social work and to guide leaders and teams through strategy, alignment, and communication of their organizations.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Absolutely! Eric and I have been married for nearly 13 years and through every season of our marriage, we have been involved in one creative venture or another. Eric took a creative entrepreneurial path after finishing up college in his mid-twenties. He worked as a freelance art director and brand consultant in Chicago and developed a deep passion for bringing creativity into a business.

I thought I was taking a more traditional path to my career — going to grad school for clinical social work at the University of Chicago and finding jobs in my field. But entrepreneurship sneaks up on some people, and that is what happened to me. I’ve run non-profit programs, evaluated state-funded programs, sat on nonprofit boards, and detoured into building marketing systems at the whiteboard video company Eric co-founded. Now I facilitate deep conversations with leaders and I am scaling an agency to bring creative, visual thinking into teams across the country.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Eric and I were both working in the two previous companies he co-founded (TruScribe, a whiteboard video production company and Squigl, a SaaS company providing enterprise-ready video creation software) and had a few opportunities to present and facilitate some visual thinking workshops for some local organizations that support entrepreneurs. After testing out our workshops, we eventually developed our own method of visual thinking and facilitation. The opportunity to bring these concepts and tools to the strategy part of the business was really exciting to us — it builds on the creative services already offered by the other companies Eric co-founded.

Initially, I was challenged by a mentor to adapt lessons from my nonprofit experience to accelerate business planning. That is not the typical direction you see nonprofit experience being transferred. We wanted to round out the cold technical aspects of business planning with the heart and soul of nonprofit logic models, to explore the purpose and ‘why’ of a business. On top of that, we wanted to apply visual thinking to this business exploration. That’s where Eric came in. Having spent the last 10 years innovating creative processes and systems at two companies he co-founded. The opportunity to bring these tools and methods together and apply them to business planning and strategy combines both our worlds together.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I call myself an accidental entrepreneur. Entrepreneurship runs deep in my family and Eric’s family. But I never considered it for myself until I found the thing that I wanted to build for the world. It took me years of being around entrepreneurship and becoming part of a community of entrepreneurs for me to change my ideas of what I was capable of. Now that I am in the world of entrepreneurship, I can confidently say that I belong and that my skills are needed in my business.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

There are so many people who support, inspire, and help my and my partner every day! We couldn’t keep going without the support of our friends, family, coaches, clients, and community of entrepreneurs in our city. Specifically, the Doyenne Group in Madison, WI and Dr. Amy Gannon, until her tragic death, helped us see what we were offering as a strong need. And now that we are co-founders as well as partners, I wouldn’t want to be doing this without my husband.

What do you think makes your company stand out? Can you share a story?

Our creative approach to business strategy and alignment is unique in three ways. First, leaders who feel alone at the top are supported and heard. Second, because they feel heard they open up and we can get to work quickly building a clear path forward. Lastly, our Constellation System of visual facilitation that makes all that possible. Our clients have rarely had an experience like ours, but they leave our sessions feeling more confident in their abilities and more able to communicate where their organization is going and why.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The first character trait is a strengths-based focus. As a co-founder with my husband, we need to divide responsibilities based on our strengths. Sometimes that means a clear division of responsibility (for example, he is creative and makes all of our branded content). But other times, we recognize that parts of a process are important for both of us to be involved in (like the initial planning) but then one of us takes responsibility for it.

The second character trait is collaboration. As a leader, I love to work with people to find their hidden interests or talents and use those skills towards a common goal. Collaboration is part of all aspects of my work — it makes our business more interesting and it gives everyone a say in it.

The final trait is curiosity. I am always reflecting on what is working, what isn’t, and the impact things are having on my team. For example, even though I have done many sessions with clients, Eric and I always debrief after each session about what went well, what worked, and what we could do better next time. Everything is a work in progress!

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

One of the ironies of entrepreneurship is that there is so much advice out there and yet, entrepreneurship can be very isolating. I’ve heard people offer the idea that entrepreneurship is supposed to be hard, which can turn into a self-fulfilling prophecy. Yes, there are challenges to it, but there are also daily opportunities to choose to do things differently.

Now, rather than accepting the idea that entrepreneurship is hard (which it inevitably is!), I take a critical look at what I can impact and accept the external factors that I can’t affect. And usually, what I can impact is significant! For example, since we have launched our business during a pandemic, we can’t be out in the world meeting people and talking about our business. But we can challenge ourselves each week to add new ways of talking about what we do to our social presence or website. So, rather than dwelling on the challenges we are experiencing, we are empowering ourselves.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

I find that a culture of open communication where employees understand what’s happening, why it’s happening and can voice concerns keeps everyone feeling heard. You don’t want people just telling you what you want to hear or keeping things from you.

Clearly defined purpose in all we do makes it easier for people to stay motivated and engaged.

One thing that I do with employees is regular check-ins where I deeply listen to their experiences and thoughts. And I take the time to compile their responses and look for themes. Employees in one department may have a very different experience than employees in another department, so I can better identify trends with these regular check-ins.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Authenticity, generosity, and consistency go a long way. When you are building your business, you are the face of it. The more generous you can be in helping others, connecting people, helping in your own way, following-through in what you promise — this will build trust, credibility, and authority.

Can you help articulate why doing that is essential today?

Authenticity, generosity, and consistency are essential today because they are the basis of good relationships with one another. If you bring your authentic self to your business, you are going to make longer-lasting, more genuine connections. it will be more rewarding for you too!

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

A common mistake I’ve seen CEOs make is trying to accomplish too much, in too many areas, and having too high of expectations of the results. CEOs and founders understandably have tons of ideas and have a good reason for needing things to grow and succeed right away. But I’ve found that setting up the most important pieces of your business first and then allowing space to grow into yourself can be a really great way to build something sustainable.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Entrepreneurship is a magnified version of a “regular job”. An entrepreneur absorbs all of the highs and lows that are typically spread across an organization. That can be very stressful but also exhilarating, especially when you see your vision come to life.

We are in the early stages of growing Relumed, although we’ve been through this journey in the other companies Eric co-founded. We are hopeful, optimistic, and encouraged by every win. But even though this isn’t our first venture, we still worry about the timing of a payment, or if we’re having enough conversations to bring in deals. Also, the dramatic highs and lows can come because your business is a big piece of you. Your idea is out in the world — how people see it, respond to it, and interact with it impacts you.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

We had developed a new workshop and the first time we presented it we ran into a few snags and realized that we had more content than we had time. People seemed to find value in it, but we didn’t feel like we were delivering what we’d hoped. A lot of work goes into developing products; copyrighting, graphics, practicing, etc. After some tweaks and some more practice, the next time we offered the workshop we hit every tone and tempo we were hoping to. The responses were great and it gave us a huge boost in confidence for the direction we were heading in.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

As entrepreneurs who have to convey confidence and demonstrate success, it’s difficult to show vulnerability. You have team members to support, partners and investors to reassure, and clients to impress. When we launched Relumed we had high expectations for growth and first-year revenue. But we weren’t equipped or perhaps didn’t realize how much more we had to do in order to reach that first peak. Many lows are the result of misaligned expectations. When I am more intentional about the process rather than the results and know that I’ve done my best, I can be more accepting of those lows.

Based on your experience can you tell us what you did to bounce back?

I’ve started writing down or taking screenshots of positive things people are saying about my business. In our work, we visualize things like ideas and feelings so that the positive ones are more tangible and we can see them better. I’m trying to compile these positive reinforcements for the inevitable lows.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

  1. Have a North Star: People refer to this in many ways — mission, purpose, why. For us, we often refer to it as our “North Star”. By keeping our vision or our north star in mind, we can plan out our big dreams (courses! Workshops! Write a book!) and our next steps (find new clients).
  2. Maintain Curiosity: When I show up in my work, I try to bring a sense of curiosity. Sometimes that is easier said than done! For example, our curiosity has led us to formalize our method of visual thinking — something that now makes it easier to teach and offer to clients.
  3. Surround Yourself with Great People: I find that riding the highs and lows is easier when you have a community and collaborators to count on. The energy and support you receive from your community can help you keep going!
  4. Recognize Your Strengths and Weaknesses: When thinking about the company we want to build, we start with our vision for what we want to build, but that is informed by our strengths. Creativity? Check! Supportive, compassionate client work? Check! By bringing together our superpowers, we can be confident that we are building the strongest company we are capable of.
  5. Something other than work! As co-founders and partners, we are constantly surrounded by our work. But, we also have two young children that keep us focused on things other than work. We also both find time for friends, family, and community who aren’t part of our work life.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

I love the idea of resilience. I have a master’s degree in clinical social work and a lot of my educational experience was around resilience — within children, families, and even communities. When I got into the entrepreneurial world, I quickly recognized the importance of resilience here too. I would define resilience as the strength and ability to get through difficult situations. Some characteristics of resilience are the ability to recognize when to double down and when to change course, internal motivation, and a sense of empathy or understanding of how others are feeling.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

I worked hard at piano growing up. I learned from an early age about how to maintain motivation and push through hard times towards a greater goal. The tenacity and internal drive I learned through my experiences with piano competitions has stuck with me and is reflected in my work today.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I don’t always keep a positive attitude. I get hit with that wave of doubt or even dread that you’ve made a mistake. But then I shift my perspective to see the whole picture. I focus on our purpose so I can envision new goals during difficult times. In my work with clients and in my own experience in building a business, I try to stay open to all possibilities for outcomes. Even the ones that are hard to deal with. We have also built our company with a strong vision and sense of purpose. Keeping those in mind allows us to see new ways forward. But I’m not always positive about it!

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

I’m not a strong advocate for a positive attitude in a leader. I believe what motivates teams and attracts clients is a clear vision and open communication. Hopefully, that is done with kindness and empathy, but I don’t tend to focus on being positive at all costs.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

We recently shared a quote on our social channels from Voltaire that says “Appreciation is a wonderful thing. It makes what is excellent in others belong to us as well.” I love this quote because it reminds me that the pursuit of building a great company is about everyone who contributes to it.

I have been careful to practice appreciation in every aspect of my life — from my volunteer work to my family and friends and finally to my business. I’m able to build something great because of those around me.

How can our readers further follow you online?

You can connect with us at We are active on LinkedIn, Instagram, YouTube, and Facebook. Thank you!

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

It was my pleasure. Thank you!

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