Wendy Dickinson of Ascend Coaching Solutions: “Sleep”

Sleep. Of course, you will have to work late, or come in early — or both. But, sleep is essential to maintain your overall health and mental acuity. I can do without a good night’s sleep for maybe two consecutive nights and then, I’m trouble. As a coach and consultant, I meet clients where they are — and that […]

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Sleep. Of course, you will have to work late, or come in early — or both. But, sleep is essential to maintain your overall health and mental acuity. I can do without a good night’s sleep for maybe two consecutive nights and then, I’m trouble. As a coach and consultant, I meet clients where they are — and that requires patience, empathy and a listening ear. I need that every day.

Eat well. Don’t deplete your physical reserves to feed the business. Each of these steps will allow you to maintain your energy, choose appropriate responses to the highs and lows, and have the stamina to go the distance. I’ve invested in my company. I have strategic plans to implement and execute. I cannot do those things on an empty stomach without adequate nutrition. Radio shows, podcasts, client meetings — all get awkward if my stomach is growling.

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 Wendy Dickinson. She is the founder of Ascend Coaching Solutions LLC, the expert guide among coaches and consultants, for thriving, viable businesses, who want to protect and cultivate their business legacy. She offers high-impact resources that unlock the varied path to profitability and resiliency. She is an expert in organizational culture within government, and business settings — offering talent optimization tools, along with value-added, consciously profitable strategies to potential investors, future prospects and strategic partners.

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?

I’m from a family of “makers” who did not have the knowledge (or access to the knowledge) of how a sound business was created. I witnessed my Dad’s heartbreak and the joy. I also witnessed the risk that entrepreneurship exposes that owner’s family to just by being in business. I benefited from those experiences. I’ve had the opportunity to be a part of growing three companies. I continue to learn every day. I believe that business is a mirror that shows me what I need to learn next.

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

Yes, my aha moment came about when I heard of a situation where someone like me might have had a positive impact on a business owner’s future.

I’m an investor in a company that had a client that had started a business back in the ’80s. The company had grown into a mid-sized business. Out of the blue the company received a call from an interested buyer who offered 30M dollars for the company. The owner wondered if he could get 35M dollars. He decided it was time to sell, so had several investment banks do a valuation and pitch. To his surprise, the company was worth much more than 35M dollars. This almost never happens. I’ve heard of this exactly once — with this case. The prospective buyer was chosen, that company spent about 1M dollars in due diligence and preparing to integrate the acquisition. The week before the deal was to close the owner pulled the deal. Totally shut the deal down. Goodbye 35M dollars+!

In hindsight, this owner had not prepared for the transition. This owner had not prepared to be an empty nester, a former business owner, or suddenly saddled with a huge sum of money without a new purpose. The deal was doomed.

That one case led me to become a business coach. I pictured that owner in the future, filled with regret. It was the right time in the market to sell that business. It was the right price. But, the owner wasn’t prepared. Only time will tell if the owner will ever sell, or for how much. Chances are it will be a harder sell for a smaller price.

See principle 1 & 5

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

Yes, I’m a natural-born entrepreneur, with life providing gut-wrenching lessons to make sure I’ve gotten the point. Growing up, I had firsthand knowledge of what a business shouldn’t become.

I come from a scrappy family. I was a surprise to my father, a college sophomore at the time (who would’ve been the first in our family to graduate college), and my high school cheerleader mother. My dad was a “maker”. He could make anything out of almost nothing. He was a trader, great at bartering. He bartered for flying lessons. He bartered for materials. He bartered for some of the ugliest cars in the universe — but that’s another story.

My Dad was a leader within the Ironworkers Union Local #5. All of his crew were high school friends. When the union was on strike more than at work, he realized that he couldn’t support 4 kids on the wages. He started his own contracting business, but, he was not a businessman.

At 14 I could see mistakes — didn’t know his numbers. He didn’t care about scheduling or running the deliveries efficiently. He liked driving around talking to the suppliers, property owners and then diving into a particular job. He worked really hard. He didn’t work smart.

In a fairy tale, this story would end well. In real life, it didn’t. The vulnerabilities in that business led to the loss of our family through divorce, the loss of our home, and a rift with my Dad that never truly healed while he was alive.

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?

My best friend, and husband, JD, has always been my inspiration. JD and I have shared the founders’ journey several times. He is methodical, patient, and has great instincts. We complement one another really well.

We met in the sixth grade. He was the only person in my grade who could touch the hall clock when the entire group lined up in the hallway — very impressive. Little did I know that his literal reach was the least of his attributes. He is my inspiration every day. One of my core beliefs is that we all need a board — for life, and for business. JD is one of my board members and he has been since we became friends all those years ago..

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

Ascend Coaching Solutions stands out, and above other business coaching firms because we recognize the challenges of navigating both life and business. We work with small to medium-sized companies to give those owners the same access to best practices as the large organizations. ACS brings the tools to the coaching relationship to build a viable business while leading a values-rich life.

One example — I have a client who juggled two businesses for a number of years. During this time, she was diagnosed with two chronic illnesses. This busy CEO also had the role of primary care coordinator for her parent. My client felt it was a failure to close the first company she started. It was no longer profitable, and it drained her energy. She felt she had to turn it around before she could let it go.

In this case, this client and her business had become enmeshed. Enmeshment comes in multiple forms and is not healthy for the business or for the client. We worked to separate the identity of the client from the identity of the business. Once that happened

With a coach, she explored other options and found one that worked for her. During our work together she formed a strategic partnership that absorbed her team and clients for a fee, delegated some care coordination for her mother, learned to increase her self-care, and devotes herself to her passion business. Last week my client shared that she feels happier, healthier and more at peace than she has in years. That’s a win!

Principle 5 and enmeshment. Develop 5 risks for owners- Enmeshment, financial clarity, MVP vs. MVP- how to manage the tension,

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?

Everyone talks about luck. I believe that I’ve curated the learning, the contacts and the experiences to create luck and recognize the opportunities it offers. I recognize the opportunities that I have had that many others do not. In addition, I am a person who has a high degree of situational awareness, is grounded, and able to hold a long view.

A number of years ago, friends Preston and Lori Campbell, JD, and I started a business called Document Warehouse. We had two goals: to build the business to sell it and to remain friends. Preston and Lori wanted to move out west. JD and I wanted to accumulate enough wealth to get out from under the medical expenses that plagued our financial future.

During the early days of Document Warehouse), Preston ran the day-to-day operations. JD and Lori held positions outside of the company.

JD had had health issues for a number of years that was a serious burden for him. Our younger daughter was born with health issues; she was in constant pain and slept very little. Caring for her, and JD, stretched our energy and financial resources.

While the company was small, Preston couldn’t do everything himself. There were times I jumped in to offer no/low-skill labor. It was boring, and tedious, but had to be done.

I remember one morning at 4:30 am I looked into the face of our crying child and knew I was at my limit. For me, that was a moment of faith. I prayed for the energy to meet the demands of the coming hours, the presence of mind to stay fully present, along with the goal of being a loving parent and partner.

In this and other situations, I pulled on my resilience and grit.I don’t avoid problems. Problems are the opportunities to gain new skills, uncover weaknesses in my thinking or perspective. I don’t hide from problems, I navigate them. I know that whatever happens, I can handle it. Document Warehouse, the illnesses of people I loved, and the impact of my contributions are layers of resilience that have buoyed me every day since.

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?

The worst advice I ever received was to “don’t get a big head” or get “too big for my britches”. I suspect both were aimed, in part, at keeping me in the same blue-collar, undereducated, financially insecure socioeconomic group I was born into. I believe the other part was because I am a woman.

Worst advice ever! I spent a lot of years downplaying my abilities and feeling unworthy.

In truth, I enjoyed great success. And, I’ve come farther than many thought I could.

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?

As a business coach and consultant, I have the opportunity to inspire other leaders to create cultures that are inclusive, diverse, ecosystems that allow each person to contribute their skills and talents to the strategies that will deliver the results the business needs to thrive. I have 4 tips:

1. Become a good listener — listen to understand.

2. Know yourself and others — strengths, skills, blind spots, knowledge gaps.

3. Practice the different kinds of decision-making — clearly communicate your responsibility in making the decision and the desire (if it’s there) to hear the input of each stakeholder.

4. Hold the vision, mission, purpose and values as sacred. Use each as the litmus test for each decision made, problem solved, initiative introduced.

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

Know yourself. Leaders are to lead themselves, others, ideas and results. Notice it starts with self.

Know your values, strengths, skills, gifts, interests, blind spots, knowledge gaps, and be that person at all times. It takes a great deal of energy to be one person in public and another person in private.

Trust, credibility, and authority within the industry begin with living and leading with authenticity. It endures as the person models vulnerability in the practice of leadership in life and business.

Note the emphasis on both life and business. I believe that one’s conduct in life is as influential as conduct in business. Life is a mirror to the soul, and business is the magnifier side of that mirror.

Can you help articulate why doing that is essential today?

Becoming a thought leader and authority in an industry may prove to be the differentiator for many companies. Look at Elon Musk’s approach to releasing Tesla’s (what could have been proprietary) knowledge into the marketplace. This allowed other players to build charging stations that fed the growth of Tesla.

Leaders who choose to step into the role of industry authority, open the door for strategic partnerships, exchange of information, as well as position the leader to view trends that may be years down the road.

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?

1. The founder doesn’t have an idea of how he/she would like to exit the business, so doesn’t prepare an exit.

2. Energy and resources are put towards short-term returns, without long-term sustainability.

3. The CEO/Founder doesn’t assign importance to, or deploy resources towards, establishing a culture that aligns with the vision, mission, values or purpose of the company.

4. Be future-ready.

5. The CEO/Founder builds the company around herself/himself and it becomes a collection of jobs, not a sustainable, viable asset.

These are mistakes that I saw as a child when my Dad started his construction company. They are mistakes I see in my clients’ businesses. To me the Ultimate Owner Experience (O)X includes:

· a values-based vision with a value agenda map

· a profit plan that builds revenue over time

· a culture that empowers each person to lead strategy design that delivers measurable results

· a Founder/CEO who is self-aware, plans for the eventual exit and lends her/his skills to building a company that solves a particular problem with an empowered, diverse group of people

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”?

I love this question. You are doing entrepreneurs everywhere a great service by posing this question to your readers. Gary Vaynerchuk has called 2021 “the year of the practitioner”. Entrepreneurs actively practice business. It isn’t a static, stagnate, formulaic state of being.

It is volatile, uncertain, complex and ambiguous — it’s a VUCA world! Holding a “regular Job” is like navigating an aircraft carrier — moments of excitement, but the entire government is there backing you up. Having your own company is the equivalent of driving a Ferrari at night on the wet pavement down the Pacific Coast Highway– it’s you, the car and the road. No backup. No crew. Just you and the car. Every move you make matters, every time.

If you are overwhelmed, confused, sick to your stomach, anxious and can’t sleep sometimes, you may have run into operations or logistical bottleneck, lost a major customer, or discovered your product isn’t all that you thought it might become. All part of the journey.

If you are ecstatic, punchy, hysterical, revved up beyond belief, at other times, you may have discovered a way to reduce fixed costs, landed a new customer, earned a huge surge in revenue or market share.

If you have times where the tasks are boring, you have to grind to get some things done, and nothing feels fun, that’s part of the entrepreneurial ride, too. Those may be the times you and your team have drilled down on a system or process that needs to be revamped, or assessing consumer demand, or developing an employee handbook (necessary but not necessarily exciting). It might be the indicator for outsourcing that particular system or process development.

Most days are a mixture of each. Building a viable asset takes every owner/founder through the highest of highs and the lowest of lows due to the investments of time, emotion, energy, and financial resources. If that’s what you’ve experienced, it’s typical.

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.

When my husband, friends and I started Document Warehouse, we thought we had a winner. It was absolutely the most exciting, gratifying day when the business was sold! And, it sold to our target acquirer, Iron Mountain.

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.

The first year that I thought I had turned a profit with my latest company, the bookkeeper discovered an error that meant that I fell short of landing in the black by 1700 dollars. So close!! It was devastating.

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

First, I allowed myself to feel the disappointment and the cascade of emotions that went with it. It hurt. My internal critic was jumping up and down with lots of negative garbage running through my mind. Then, I went to my Board. Each offered the guidance I needed to integrate the experience.

Then, I remembered that I had the practice to implement. I challenged those negative thoughts. I remembered that nothing had changed. The numbers were the numbers. My perception of the numbers had changed.

My Board worked with me to view the numbers as numbers — messages for course corrections. So, it opened the door to see this as an opportunity to review my costs, dive into the numbers and examine the systems and processes that support my lead generation and client onboarding. All were worthwhile activities.

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. Meditate. This is your go-to. Meditation allows you to be fully present in a situation while you maintain an emotional reserve. It’s your key to choosing a response versus reacting. This practice allows me to show up in any relationship as my best self. I’m aware of my darker tendencies, and yet I have the presence to hold the long view.

2. Sleep. Of course, you will have to work late, or come in early — or both. But, sleep is essential to maintain your overall health and mental acuity. I can do without a good night’s sleep for maybe two consecutive nights and then, I’m trouble. As a coach and consultant, I meet clients where they are — and that requires patience, empathy and a listening ear. I need that every day.

3. Eat well. Don’t deplete your physical reserves to feed the business. Each of these steps will allow you to maintain your energy, choose appropriate responses to the highs and lows, and have the stamina to go the distance. I’ve invested in my company. I have strategic plans to implement and execute. I cannot do those things on an empty stomach without adequate nutrition. Radio shows, podcasts, client meetings — all get awkward if my stomach is growling.

4. Learn — for the whole of your life. Read, or listen to books, podcasts, and music. Give your mind the opportunity to learn and stretch. You should wake up expecting to learn 2–3 things every day. This is the practice of self-awareness and internal motivator. This practice helps you maintain your competitive edge. My clients get down into the weeds of their businesses. They tend to miss trends and hold onto outdated systems because they are comfortable. But, once they start reading or listening, they can’t undo the knowledge they now hold. It’s transformational.

5. Exercise. Exercise outside whenever possible. You were designed to be an outdoors creature. Give your eyes, brain, and body the chance to connect with the outdoors.

As an entrepreneur, you bring your humanity to the business. There is a mind, body and spirit connection to that business. If you are mindful, well-rested, well-fed, curious, and physically fit — you can handle every single thing that the business landscape can dish out. It won’t be easy. It won’t all land you in the millionaires club, but you will be rich in wisdom, experience and resilience.

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?

To me, resilience is the ability to navigate any situation to the best of your ability, curate the learning from it, and apply it to the next adversity.

I believe that resilient people are willing to learn, and be vulnerable. The resilient person realizes that bad things happen, aren’t always preventable and those bad things can happen simultaneously. I also believe resilience can be learned.

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

During the days when my Dad’s construction company was growing, he struggled to maintain the equipment, deliveries, and coordinate his guys between jobs. We were building our own house at the same time.

One day, my Dad asked me to come and give him a hand with a job. I was 14.

We were building our own house at the same time. And, it was time to prepare the floor of the 2 car garage and workshop. He had had gravel delivered that needed to be spread before an 8 am concrete delivery the next day. His plan was to use the backhoe to move the gravel, the spreader to spread it, and be done in a reasonable period of time. I happened to be with him. The Backhoe broke down, the spreader didn’t happen to be on site after all, and it was dark.

We moved that entire load of gravel, spread it and had it done by morning — all by hand. This was pre-iPod. We pulled the trucks around, used the headlights and shoveled it all by hand. We sang, We argued. We didn’t give up. I saw that man do that kind of thing time and again. He was the kind of person that you could knock him down, kick him, and he would get right back up. He had a deep reserve of grit.

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

When I have followed my own recommendations of the 5 Things Needed To Successfully Ride The Entrepreneurial Highs and Lows, yes. I look for the light in difficult situations. Difficult situations pass. They all do. Over time, I’ve found that when s*#! hits the fan, you can’t avoid it, you’ve gotta go through it.

I know that I am strong, capable, and have a great deal of resilience. That self-knowledge helps a lot.

One last thing, there is no cosmic scorecard in the sky. If you happen to be someone who feels like bad stuff keeps happening over and over again, it isn’t because you are marked. There is not a limit to how many bad things can happen to you in one day or one year. Triage the problems and keep your eyes on the mission, vision, and purpose. The reason you write it down is for times of trouble, not the good times. You need the reminder of why you’re in the game.

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.

Leaders underestimate the extent of their influence. A leader can face a difficult, scary or challenging situation and do it without losing their equilibrium or acting as though nothing is wrong.

If the team and your clients recognize a terrible situation is on the horizon and the leader is willing to honestly identify what she/he sees, listen to the voices of key stakeholders, and then lead through the iteration of the ideas to the results, that is a hell of a leader. During COVID every business coach in the country partnered with their clients to formulate survival and recovery plans. I certainly did that with my clients.

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?

Teddy Roosevelt’s, Man in the Arena. I was reminded of this quote back in 2016 by Brené Brown. Hearing of the many ways that business owners sabotage their exits from their businesses, inspired me to become a business coach. This quote is the best I’ve come across that communicates that feeling of extreme vulnerability, stupidity and nausea when an entrepreneur realizes that s#@* is about to hit the fan.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows, in the end, the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

How can our readers further follow you online?


Linked In Wendy Burnette Dickinson

Facebook Ascend Coaching Solutions

Twitter wendybdickinson



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

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