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“Reach out just to say hi and see how they’re doing”, With Jackie Minchillo

Reach out just to say hi and see how they’re doing — even if you don’t have time to call, at least send a text. In this landscape of social distancing, people who already struggled with anxiety before are the ones feeling the most isolated and worried about the unknown. Let them now you’re still […]

Reach out just to say hi and see how they’re doing — even if you don’t have time to call, at least send a text. In this landscape of social distancing, people who already struggled with anxiety before are the ones feeling the most isolated and worried about the unknown. Let them now you’re still there.


As a part of my series about the the things we can do to remain hopeful and support each other during anxious times, I had the pleasure of interviewing Jackie Minchillo.

Jackie is a former corporate ladder climber who discovered the path of serial entrepreneurship through a 4-year digital nomad stint abroad. Today along with her husband she co-owns Pineapple Development (eCommerce web development), Joy of Cleaning Florida (residential/commercial cleaning in St. Pete, FL) and is also the co-owner in a real estate investment group. Outside of growing businesses, Jackie is an avid writer passionate about living life by intentional design, travel, plant-based nutrition, yoga, CrossFit and animals. Find her on Instagram at @jackie_minchillo


Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Sure! I have always been a writer, passionate about storytelling, and that has been the common denominator in all of the twists and turns my career has taken. I studied journalism with aspirations to be a television reporter; however I graduated from university in 2009 at the height of our last great recession and small television stations (if they were hiring at all) were not offering salaries to entry-level reporters that were enough to live off of. When I received an offer for $18,000 a year for a full-time job, I knew I needed to pivot with my plans and QUICKLY.

Despite my parents being, hands-down, the two hardest working people I’ve ever known, we were a socio-economically depressed household and finances were always an intense struggle for our family. I was the first in my family to go to college and graduate with a degree, and I didn’t have anyone to help me financially; so not making a living wage out of college when I was already up to my ears in student debt wasn’t an option. I ended up working in direct sales for a brief stint (door-to-door cable sales) before taking a job with a digital marketing agency. And eventually found my way into publicity where I worked closely with the media on behalf of my clients.

A culmination of the general corporate grind wearing on me, not being heard by leadership, frustration with organizational bureaucracy and knowing I wasn’t being compensated properly or fairly for my expertise and value (and my husband feeling much of the same) led us to jump ship. Clear the slate. Start from scratch. We quit our jobs, sold everything we owned, sub-let our overpriced Chicago apartment and moved to a small beach town in Costa Rica. What was thought to likely be a 1-year hiatus turned into 4 years of redesigning our life in paradise.

We knew we both aspired to change familial patterns and rewrite our financial future so that we would not have to live through the same struggles we saw our parents deal with growing up. And we knew it was important to us to be our own rule-makers, and maybe more importantly, rule-breakers, if we saw fit.

The first company we founded together was our eCommerce web development agency, Pineapple Development. With 15+ years of experience in eCommerce my husband’s background in technology and omni-channel digital retail, coupled with my agency and branding experience felt like a perfect fit. We set out to create an all-remote, low overhead agency that put the human element back into business while boosting the bottom line for our clients. We still operate that way today. We got a lot of flak from people in the beginning, telling us we’d never be able to run and grow an agency without having a physical office at some point. Today in the midst of the COVID-19 pandemic, it feels reassuring to know we were ahead of the curve in developing systems and a workforce that can be productive from anywhere in the world as we watch other companies struggle and scramble to figure out what their day-to-day looks like with their workforce suddenly working from home without a plan.

Since then, and since our return to the United States in 2018 when we landed in St. Petersburg, Florida, we have acquired a residential and commercial cleaning company and started a real estate investment partnership with another husband and wife team. What we’ve learned about ourselves is that we have widely varied interests and we appreciate the opportunity to design a life in which we can tap into a myriad of skill sets and focus areas. I am story telling on behalf of brands still every day, but now they are my own. And we are living a life in which we make our own rules, have removed the cap in terms of reaching for our own potential and financial dreams and have discovered that above all, we see ourselves teaching and encouraging others to do the same based on our personal experience in the future.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

“Big Magic” by Elizabeth Gilbert is one of my all-time favorites. I find her writing around fear and utilizing it as a tool rather than letting it be the driver to be incredibly powerful especially when it comes to decision making and risk. And also “Permission to Feel” by Marc Brackett. I think we live in a society that has completely downplayed, if there’s even a clue at all, as to the importance of emotional intelligence in every facet of our society from the way we raise our kids to the way we lead in business. This book was a beacon of hope for me in affirming that I’m on the right track by doing things differently, intentionally — and I do think we’d be able to tackle many of the greatest problems we face as a society if emotional intelligence were a larger part of our conversations and philosophies. We’re humans, not robots, and so we need to nurture our nature rather than suppress it.

Ok, thank you for all that. Now let’s move to the main focus of our interview. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have heightened a sense of uncertainty, fear, and loneliness. From your perspective can you help our readers to see the “Light at the End of the Tunnel”? Can you share your “5 Reasons To Be Hopeful During this Corona Crisis”? If you can, please share a story or example for each.

  1. Opportunity lives in chaos and adversity. The greatest successes of my life thus far have all been born out of great challenge and struggle. Holding my grandfather’s head in my lap as he took his last breath when I was 21 taught me the importance of saying ‘yes’ to life. Taught me the value in taking a chance. Taught me the importance of taking action and making decisions without hesitation. That sort of experience with death at a young age will teach you what the expression “live each day like it’s your last” really means. My husband and I lost everything in a total-loss fire in our twenties. That experience allowed me to let go of my attachment to physical things and not only prevented me from making some potentially financially disastrous decisions in my early adult life, but also freed me from the thinking that I needed to have certain things in order to appear successful. That kind of mental shift can jolt you into focusing on the things that are truly important and free you from having your vision clouded by false appearances and perceptions. Having to manage essentially our own version of hospice care (because hospice care as we know it in the United States is not really a thing in Costa Rica) for my Mom (alongside my Dad and my husband), and holding her hand as she gasped for her last breath in our guest bedroom, not even 2 months after a stage 4 lung cancer diagnosis was the catalyst for massive change in the direction of my life in my late twenties, both spiritually and in business as the decision to take the leap and bring Pineapple Development to life came a few months after her passing. Having to pull the plug on already-in-motion plans to build a home in Costa Rica to move back to the US was devastating in its own way. My husband is originally from Brazil and is a US green card holder; and we were told to maintain lawful status in the US we needed to move back or he could give up his green card. We could have given it up, but going back to quick decision making, we knew our time in the US was not completely a thing of the past. While leaving the life we had built there behind was gut-wrenching, it quickly became clear we were in the right place when our other two businesses came together naturally, shortly after our move. And these are just a few examples. We’ve dealt with legal stressors, massive credit card debt, being betrayed by business associates; these situations always have the potential to break you or fuel you. CHOOSE the latter.
  2. Is this a shift society needed? I see incredible connection going on in the midst of social distancing. It has become the norm in our society that children are raised in large part by people other than their parents. On the whole, I’ve seen more people playing outside with their kids in the backyard or in the park or going for a jog or a bike ride than I’ve seen probably since I was a kid myself. You can only watch so much Netflix and YouTube (we’re also finding space to recognize those limits which is refreshing). The creativity I’m getting to see via my Facebook and Instagram feeds by parents is nothing short of incredible. Families are eating meals together without a set timeline because there’s nowhere they have to be. For me personally, we’ve had acquaintances and business associates reach out to schedule a Zoom call, simply to chat. To get to know each other better, without an agenda. There’s nothing but good to come from this when it comes to human connection.
  3. This experience is bringing us back to our true nature in many ways. On the superficial level for example; people are canceling hair appointments, not getting their nails done, skipping botox sessions, not going to eyelash extension appointments, or their next spray tan. Gyms are closed so we’re getting creative. Using the stairs in our house, getting OUTSIDE and going for a walk, using random household items as props and weights — remembering in a flood, how creative we can be when we need to be. Perhaps as a collective humanity, our need for additives from the outside to feel beautiful or whole will be curbed and altered at least a few notches back in time where we were kinder to ourselves because we didn’t have a reason not to be.
  4. A crash course in being okay with CHANGE. I saw a YouTube video at some point a while back where the gentlemen talked about the lines on a heart monitor and how when they’re jumping up and down and constantly changing it indicates the person attached is alive. When the line is flat, the person is dead. Change is in fact the only constant any of us can count on, and yet sometimes we get so wound up resisting and fighting change in hopes that we can keep things the same, keep things comfortable, etc. when really sometimes change is what sets us free from something that has been holding us back. I will say for example, our focus in our web development agency has always been larger companies looking for large monthly maintenance retainers and high-end website builds (typically in the $60,000-$150,000 range) — but this pandemic experience has sounded the alarm for us on the importance of not forgetting how to pivot. We have been inspired to look at lower cost solutions that would also allow us to serve the businesses right here in our own backyard. As soon as the government mandate came to shut down restaurant dining rooms, we began working on a low-cost, templated solution for restaurants to house their menu online and offer an easy and convenient way for customers to order for curbside pick-up. Something like this is something we’ve been resistant to in the past, because it’s not our “ideal” model, but we’ve been humbly reminded that part of success in business is being agile and able to pivot to serve the CURRENT needs of the market.
  5. Unity. This is the first time in each of our lifetimes that a SINGLE event has quite literally brought the whole world together. In divisive times on so many levels, all of the sudden we’re all in the same boat. The person you argue with about politics is dealing with this too. The person whose religion you can’t understand is dealing with this too. The person whose house or car you envy is dealing with this too. Your neighbor with too many wind chimes is dealing with this too. Your child’s teacher whose teaching style you can’t stand is dealing with this too. The person who has a different stance from you on abortion or gun control is dealing with this too. I don’t think there’s an example necessary for this one — this kind of common ground and mutual experience — if we’re all willing to lean into it, can only bring about an enhanced level of compassion and understanding for one another so long as we collectively make the decision that that’s what we want out of all of this.

From your experience or research what are five steps that each of us can take to effectively offer support to those around us who are feeling anxious? Can you explain?

  1. Reach out just to say hi and see how they’re doing — even if you don’t have time to call, at least send a text. In this landscape of social distancing, people who already struggled with anxiety before are the ones feeling the most isolated and worried about the unknown. Let them now you’re still there.
  2. Share ideas of things that help you, through whatever channels are available to you. Personally, I’ve been using my social media to share my own personal practices I use for grounding and centering — from meditation to little sticky notes I keep on my computer like the one that says “I derive peace and strength from calmness. I am relaxed, calm and secure in the knowledge that everything is perfect.”
  3. Share resources you know of. If someone expresses a struggle to you and you’ve heard of resource that might help them be sure to pass it along. From online coaching resources to the Florida Disaster Relief survey for small businesses — I’m constantly passing along resources if someone expresses a worry to me and I’ve seen something that may help.
  4. Encourage them to take good care of themselves through nutrition and exercise; taking care of the body helps take care of the mind.
  5. Be calm; just like chaos, calm is contagious, and we can choose what we pass on to others. If you’re having anxiety yourself, don’t unload on a friend who is also struggling. Save your own venting for someone you know you can count on who is operating from a clear, calm headspace and then pass THAT on to those you know who are struggling with anxiety. And work WITH your fear. Encourage those you know to speak their fears out loud. Suppressing fears or pretending they don’t exist does nothing but keep them inside your body and mind to torment you. Speak your fears out loud at least once a day and release them from your physical body, followed by affirmations such as “No matter what I fear, I completely love and accept myself as I am today.” This was a practice I saw online through a coach and teacher that I tried and found massively helpful and there are lots of similar practices that can be found online as well.

What are the best resources you would suggest to a person who is feeling anxious?

Meditation. If you don’t “know how” now is a great time to explore. Personally, I use the ‘Calm’ app.

This is not a resource per say, but intentional social media breaks is important, especially at a time of worldwide chaos. Consuming too much information especially from potentially non-reliable sources can be both a mental and even a physical drain, and if you’re already feeling anxious, information overload will only make it worse.

Using the power of your own breath is key. I find this YouTube channel particularly useful.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

I don’t even know who to attribute this to and I know there are several variations, but I love “Failure is scary. But do you know what is worse? Regret.” The way I see it, failure always teaches us something and while it can be painful in the moment, eventually the lesson that comes from it will bring you peace while regret will nag at you forever. This reminds me to never hesitate in doing something or making a decision because of a fear of failure.

The best example I have of this is that my husband and I at one point made a decision to invest more than $60,000 in the real estate education and mentoring course. Shortly after we invested, the company was shut down by the government for deceptive practices and false earnings claims and we never actually received any of the mentoring and resources we were supposed to, and we did not get the money back. It would be easy to look at this as a failure; but because of that program, we started listening to a particular real estate Podcast where we got a single idea from an episode we listened to which led to the conversation that started our now real estate partnership. Though we didn’t “receive” what we were supposed to for the investment, the seed was still planted as a result which set us down a path to a very exciting business venture we’re incredibly grateful for.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to see a movement in vulnerability after this coronavirus pandemic is over. I think it has inspired people to start communicating and sharing in a more raw and authentic way than we’ve seen up to this point in the digital landscape we live in today; and so much of the institutionalized and corporate facets of society have struggled for so long with a disconnect from our own humanness.

This could be done through many avenues but in particular, intentional decision making. Before making a decision, every person commits to gut check:

  1. Am I making this decision based on the influence of other people?
  2. What will this decision say about my integrity?
  3. How will this decision affect other people?

Being honest with ourselves about these questions I believe would lead to heart-centered decision making and I believe after a collective experience like this pandemic, people will be more capable of thinking this way.

What is the best way our readers can follow you online?

Instagram: @jackie_minchillo LinkedIn Facebook

Thank you for these fantastic insights. We wish you only continued success in your great work!

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