“You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.” — Steve Jobs

The responsibility of the individual that dares to break the mold is seeing the vision and charting the course. In other words, envisioning the art and creating the art.

For a majority of my life, I’ve seen myself as the artist, the one doing the painting. Leveraging the tools around me to design and create my own life. However, recently, in this exciting stage of transition, I see myself as the paintbrush. The tool being used to create a masterpiece. Explaining why the dots are only connected, looking backward, and not forwards.

You’re Coming Up On A Year Perro...

Article III, Section VI, of the parenting handbook, advises parents to have the most difficult conversations with their child in the car. On May 30th, my dad rented a Uhaul truck to move my sister’s stuff out of her old apartment. It was our first time being in the car alone in a couple of months, so I knew he’d use the opportunity to exercise Section VI of the handbook.

Within 5 minutes of being on the road, the questions came. “So, what’s up with you, how’s business? What’s your plan?  It’s approaching a year since you’ve left PwC.” 

Ironically, despite anticipating the questions and roll playing my responses in my head prior, I was still taken back. I began by updating him on how the week prior, I lost a deal three days before closing, but was working on a couple of other deals.” To which he replies, “So what is your plan? Do you want to be a flipper or build a portfolio of rental properties?”

Eager to respond to demonstrate that I was intentional about my journey, “I plan to acquire rental properties.” I walked right into his trap, and by the time I realized it was too late to backtrack. He came with the mean counterpunch. “So have you thought about getting a full-time job so you can save money? It may help you get to your goal faster. Also, having a W-2 income will help you qualify for a loan.” 

Surprisingly that week, I spent a significant amount of time thinking deeply about my next move. The deal I lost was a major gut check. It seemed like everything in real estate was working to my demise and that it may be time to re-route. 

So instead of meeting the question with my normal resistance, I said, “I’m trying to figure things out myself. I’m spending the month of June to figure out my next move. I don’t want to move out of desperation. I want to ensure that my next move is the right move.”

Moreover, throughout the month of June, three separate events led me to my answer. 

  1. June Article Podcast
  2. June Guest Podcast
  3. Networking Event. 

June 4th - Article Podcast:

At the beginning of the Different Not Inferior podcast, Danny mentioned how he started applying to jobs because he felt like he was leaving money on the table. Just having the conversation with my father a few days prior, I brought up how I was struggling to figure out if I should look for a job. Expressing that I couldn’t see myself going back to my former employer or any company like it.

He responded, “if you want to hop back in (job market), you can’t hop back in and go back to what you came from because what you came from you hated... You can hop back in and be a copywriter... So don’t box yourself into what you left doing because you’ve picked up other skills that people need too.”

For a while, I was against pursuing writing as a career. Afraid that my writing skill-set was limited to BYLU. Not having the credentials or the training  I didn’t think I was capable of providing professional writing services. However, being open due to the circumstances, the comment got me thinking, that maybe I was running away from my destiny. 


June 11th - Guest Podcast:

Then on the guest podcast episode, Olayide our guest discussed finding her dream job a couple of years ago, but now realizing that her dream is changing. 

“You’re allowed to have your dreams change. If you are fortunate enough to find your dream job and it doesn’t change, thank God for that. But if it changes also thank God for that because that means God has something else planned for you, that’s also necessary. And the way I see it, my current position is going to have an effect on what I do next. How? I don’t know. Your dreams can change. They are allowed to change.” 

Not directed at me, yet the message spoke to my spirit. I began to think; maybe my dream is changing. Perhaps instead of real estate as the focus, and writing being the side project, I need to make writing the priority. Funnily, in a conversation earlier this year, I said, “I’m not sure what’s going to give me my breakthrough, real estate or writing.” 


June 20th - Networking Event: 

"The key is not to try to become the person you used to be. A comeback is not a ‘go back.’ Trying to go back will frustrate you even more. Find your new assignment." — Tim Storey

During my two year stay in NYC, I went to at least one networking or panel discussion event a week during the summer. On the morning of the 20th, I came across a link for the DC Young Professional Mixer. Missing NYC summers and wanting to ensure that my networking skills were still sharp, I attended. While there, I ended up talking to some people who work for my former employer. We had a good conversation, but at times there was a bit of deja vu. It felt like I was looking at an old version of myself.

At that moment, things became clear. I had outgrown that place, and going back would be like putting on old clothes that didn’t fit. In other words, it would be a step back rather than a step forward. Moreover, by the end of June, I’d made my decision. It was time to put more effort into my writing career. And like quitting my job in September, the easy part was coming to a decision. The more challenging part was telling my parents. I planned on having the conversation by the end of the month, but delayed, until one day in July. 


Conversation with Mom

My mom knows very little about my life as a writer/podcaster. She’s aware that we have a blog because she’s read some of the articles I’ve posted on Linkedin. But she has never seen the blog website and is unaware that I write articles monthly. 

Why Nathan you may be asking? It’s likely one of the following or a combination of both.

Option 1:

As I’ve discussed in several other articles, my mom was distraught when I quit my job. When I moved back, there was a lot of tension in the house, and our relationship suffered as a result. For a couple of months, my only time of peace was in between her departure for work and arrival home. The second week into my return, to make matters worse, she had a staycation. So instead of being home alone and having the freedom to do my own thing, she was there observing my moves and assessing what I was doing with my time. 

After a couple of days, she inquired about my schedule. Reluctant to share at first knowing the question was out of judgment rather than genuine interest. I gave her a brief rundown. “I wake up, pray, go to the gym, write for 2 hours, then start doing work for real estate.” When I mentioned writing, I could sense the uneasiness in her spirit. Then, her comment, “writing?” sealed the deal. 

I made up in my head that she was unhappy that I was not spending every waking hour trying to build my real estate business. So after that moment, I decided not to discuss my writing until my business was financially stable.

Option 2:

Second, since all my articles are personal and provide an in-depth look into my thoughts. It felt like giving her access to the blog was like, allowing her to read my diary. And our relationship didn’t have that level of transparency, so I wasn’t comfortable sharing yet. At the time, the potential heartbreak of my evolved state not being accepted outweighed the potential benefit of letting in my mom. 

Also, my blog posts humanize my parents, meaning it exposes some of their flaws. And in the past, they perceived constructive criticism as an attack rather than an expression of my truth. So knowing my mom’s inquisitive nature, I knew she’d read every article to see if I talked about her or our family issues. And that my articles could serve as ammunition in an attack against me. Having heard E.T. and the challenges he went through with his mom after he released a family secret to the world in his first book. He mentioned how she went months without speaking to him. And I wasn’t ready to deal with that yet. 

"The relationships that thrive are the relationships that know how to reinvent and resuscitate themselves so that you can have different versions of yourself exist there." — Esther Perel 


Spill the Beans Mom

July 4th, I walked into the house after recording the Change + Growth = Transformation podcast episode with Danny and met my mom in the kitchen. Curious about what we were up to, she began to inquire. I tried to be short with my answers, but she met each response with a follow-up. So finally, I took a slight pause and said to myself well, Nathan, you have been thinking about sharing this part of your life with your mom. Maybe the time is now. So I confessed that we were recording a podcast. 

My response opened the door to an hour-long conversation. Where I gave her more insight into who I am as a person. Sharing my interests/passions, and providing a life update now that I’d hit the nine months mark since leaving PwC. The conversation went well. It was enough for her to walk away with a better understanding of me and some peace of mind. But still, only the first of many conversations to bring her up to speed with my life. 

I realized that the next step in our relationship is for us is her accept that she doesn’t know me. She voiced on numerous occasions that she doesn’t want to be the parent were people in the street know her child more than she does. So for concurrency, she approaches our conversations as if she really knows me personally.  


Spill the Beans Dad

On July 18th, my dad asked me to come to his office to fill out some paperwork he needed for his business. Going in, I knew that he’d led with his business then eventually get into my own business. And in typical fashion, he asked how things were going since our last conversation. Already opening up to my mom, I knew it was his turn to get some insight into me as well.

I discussed how I’m not opposed to getting a full-time job to provide some stability, but it wouldn’t be in the industry of the companies he suggested. Instead, I was looking into copywriting to monetize my writing gift.

Surprisingly, there was no resistance. He said, “that’s a good business you are considering. I even need that for my own business. Content is important these days, and all businesses are trying to produce more content. From podcasting to having a social media presence.” 

Well, that went better than I expected. Lol Later in the conversation, he also mentioned how he had access to a podcast recording studio. In my head, I thought wow. Danny and I have been thinking about how to get camera’s and add the visual component to our podcast, and my dad has access to an entire studio.

I guess that’s the downside of not having a transparent relationship with your parents. There are ways that you both can help each other that you may not even know. 

Being misunderstood by people whose opinions you value is absolutely the most painful. — Gloria Steinem

On the surface, it may seem like sharing my blog with your family isn’t a big deal, but to me, it is. 

Growing up, I knew that unlike my sister, I’d have an untraditional path. The first sign was my love for football. I had dreams of going to the NFL. However, football wasn’t a career in my house, so after being discouraged a few times, I kept the dreams that didn’t fit within the traditional mold to myself. When asked by adults what I want to be when I grew up, I’d respond, “IDK.” knowing deep down it was to be a football player.

I envied the kids whose parents supported their ambitious dreams since mine came with resistance or discouragement. I felt like they refused to understand me. From promoting parties in high school to leadership positions in student organizations on campus, they didn’t seem to get it. 

As I got older, I developed a one-strike policy. After, the first sign of resistance when I shared my interest in something, I’d stop sharing that part of myself. Instead, I’d do what I wanted and inform them on a need to know basis. 

So this month was a  big step for me. It strengthened my relationship with my parents, and the conversations extended my runway to “figure things out.” I was no longer limited to the one-year time limit I initially set. Nonetheless, if you, like myself, have a secret life that your parents do not know about consider taking steps towards sharing that part of your life with them. It won’t be easy, but it will be worth it.