I should have quit my job sooner.

This is page 257 of Eyes On The Road

This is page 257 of my new book, Eyes On The Road—when I wrote it, I was thinking about that job that I should have quit at least six months sooner.

2016 changed my life, forever—it was the year that I realized there was no point in clinging to the illusion of stability. It was the year that I became a full-time entrepreneur.

It was the year that I walked into a work meeting for a progress report, and walked out of said meeting with paperwork confirming what I already knew—that the life I wanted wouldn’t include my current place of employment.

I walked out of the meeting with a “plan” that my boss had written up to close the sales gap that I was being blamed for—there was no mention of the fact that our sales team was under-staffed, only unrealistic goals that I had to meet in order to avoid being fired.

I felt frustrated, but clear.

This wasn’t the first time thoughts of jumping into entrepreneurship had crossed my mind. I had been waiting for the sign that I was “ready” to leave my job—but in that moment, I knew that there was nothing left to wait for.

I released the illusion of a “safe” or “stable” job and decided that it was time for me to build something for myself that no employer would be able to take away. I’ve worked day jobs since then, but I’ve been extremely clear about the temporary nature of their purpose in my life.

In the weeks after my quiet decision, I felt a wave of excitement rushing through my body. My job had been paying my bills, but it had also been depleting my creative energy, distracting me from my true career aspirations, and keeping me complacent. I was stagnant, and I knew it. In hindsight, my disinterest should have been the only evidence that I needed to move on with my life.

Why did I need to wait for a “sign” outside of my own disinterest and stagnation?

Why did I waste my time and my gifts working for an employer that saw me as expendable?

What was the point of hanging around for a stable check if it wasn’t actually….stable?

That same day, I made a commitment to myself to stop lying to myself about what I really wanted—out of work, and out of life.

This page of Eyes On The Road is a testament to that commitment—it’s a loving reminder that we should be willing to take risks for the causes and beliefs that make us light up inside—not just for an employer to offer us the illusion of stability for 18 to 24 months.

My first months as an entrepreneur were tough, but if I had to go back in time, I’d do it all over again—because if I didn’t learn to fight for the life that makes me happy in 2016, I wouldn’t be enjoying the life that I live in 2023.

It’s been over seven years since that day I met with my boss. I believe that my entry into entrepreneurism was inevitable, but if I could go back in time there are three big things that I would do differently in my first few years working for myself—or, for that matter, these are things that I would do for myself whether I ended up working for myself, or not.

1. If I could go back in time, I would have done a better job of balancing my creative instincts with sharper market analysis.

I’ve always been a hard-working person, but I haven’t always used my energy wisely.

Early in my journey, I just decided to “go for it” without even knowing what that should look like. I tried, and failed, and tried again, and eventually made headway—but given all of the information available to me on the internet, I know that I could have saved myself so many nights of frustration and confusion by looking more intentionally at the intricacies of successful businesses, entrepreneurs, and creatives operating in fields that I was trying to get into.

I saw a lot of the “best practices”, but was naive enough to believe that I could become the exception to the rule. Truth be told, in some ways I did just that—but the success that I’ve seen (in spite of my hard-headedness) does not negate the fact that I could have walked an easier, more easeful path had I devoted just as much energy to studying the game as I did to playing it.

If I were you, I would:

• Get clear on trustworthy media outlets and experts that are breaking down news, trends, and predictions in industries that are relevant to you and your target audience. Find ways to incorporate them into your social media feeds and e-mail inbox. Prioritize them just as much as you prioritize the empty entertainment you get out from your tik-tok feed. It’s smart to learn from experience—it’s wise to also learn from people who have walked paths that run parallel to your own.

• Spend at least an hour every month working on your business—not in it. Take a step back from the “grind” and give yourself a chance to synthesize your thoughts as to how you can work smarter. Use sources that you trust to validate the assumptions that come out of this reflection time, and put them to use, moving forward.

2. If I could go back in time, I would have asked for more help and guidance from my friends, family, and professional colleagues.

Before all of those “build in silence” memes made their way around our Facebook feeds, I was too scared to ask people for help when I needed it the most. I told myself the lie that many of us believe, whether consciously or subconsciously—that asking for help is a sign of weakness. I let a potent mix of fear and pride isolate me from the people I needed—many of whom were actively asking me how they could show up for me.

And so, I stumbled around, in the dark, by myself. I decided that every lesson needed to be hard-earned. I would tell my friends about what I had been going through in hindsight, only to realize that my recovery could have happened with a lot more ease had I simply been willing to reach out. It’s past time for all of us to let go of the myth of being “self-made” and to opt into the concept of being village-supported. We all live better lives when we all commit to showing up for each other, and letting other people show up for us.

If I were you, I would:

• Ask people for help and let them tell you “no” instead of not even giving them a chance to say “yes.”

• Build a small list of the people you know are genuinely cheering for you, and ask them individually if you can add them to a quarterly email list. Once a quarter, send them a concise email expressing gratitude for their support, sharing exciting work/life updates that you’ve experienced, and asking for any help that you may need as you continue to navigate your career. You’d be surprised at what happens when you’re willing to put yourself out there and keep in touch with people more intentionally.

• Check in on your people when they cross your mind—not in a transactional way, but genuinely. Caring about people is a foundational building block for healthy relationships. Transactional relationships are alluring when you’re operating from a space of desperation or scarcity, but ironically enough, showing genuine care and concern for people regardless of what they can do for you in the moment leads to a

3. If I could go back in time, I would have been more thoughtful about my 10-year plan while building my 1-month plan.

Generic mantras like “follow your dreams” helped me to keep going when I had no idea what I was doing. Sometimes, staying in motion is enough to make progress—but at some point, you have to get very specific about what you’re moving towards.

Sometimes, you need to zoom out and think about your end-state career goals so that you can distinguish between fool’s gold and truly valuable opportunities in the present moment. Had I done that earlier in my career, I know that I would have avoided a trap that many of us fall into at some point in our careers—chasing the dopamine of social engagement and other vanity numbers without taking into account how they play into a long term strategy.

I would have been able to avoid income droughts by maturing my businesses more quickly and diversifying income streams more intentionally. I would have been clear about what matters, and as a result I would have been able to avoid seasons of burnout that came with all of the busy work that I kept assigning myself to avoid answering the questions that really matter.

If I were you, I would:

• Put pen to paper at least once a year to reflect on the most exciting moments you’ve experienced, the most frustrating parts of your business, and the things you’ve grown to admire about other people and the way that they live their lives.

• Turn this reflection into guidance about what you should be working towards. Your businesses and income streams should serve who you are, and what you care about. Too many of us are contorting ourselves to fit into ill-fitting boxes that we chose to walk into, of our own accord.

• After you clarify what your 10-year vision looks like, think constructively about the monthly, quarterly, and annual benchmarks that you can work towards as you make progress towards the 10-year plan that makes you light up inside—not just the one that feels logical.

Sidenote: I’m thinking about turning some, or all, of these three concepts into free workshops for my paid Substack subscribers—if you’re reading this, that means YOU!

Comment if you’d love to hear me expand upon any of these concepts in a live workshop setting to start 2024.