Entrepreneurship is overly glamorized and the 9-to-5 is overly villainized.

It doesn't matter if you own a business versus work for a business. Both can be equally miserable if you lack the self-awareness and confidence to find the right fit for you.

Needless to say, pausing my entrepreneurial journey in May 2020 to go work for VEED was a big decision to mentally process. Stopping was a choice that forced me to question the messages we’re marketed on a daily basis like:

"if you don't build your dream someone else will hire you to build theirs".

My mind was like…

  • What if I’m supposed to be in 100% student mode right now as an employee. And then–in a more experienced, self-aware, and mature chapter of my life–I use these teachings as an entrepreneur?
  • Doesn’t reporting to your boss vs making your own clients happy have equal potential for either of them to make you super miserable or super happy?
  • Can’t helping someone else build their dream also in a way be my dream place to be in this chapter of my life?
  • Do the people who preach about being your own boss live fulfilled lives rich in self-awareness or are they mindlessly parroting stuff?
  • What’s so terrible about working for someone else if you actually enjoy working with them AND love the product you’re working with?
  • Does stopping my entrepreneurial journey forever or for now make me a failure?
  • If I’m not “supposed to” be an entrepreneur. Is that really such a bad thing?

This blog is ½ unfiltered rants shaped by my experiences and formed opinions from those experiences. And it’s also ½ my story with advice sprinkled in.

My goal for this post is to encourage questioning and self-exploration so you can explore and define what makes you happy. I’m not here to tell you what you should want. It’s nobody’s place to do that.

Two types of people who pitch entrepreneurship

I’ve come across two types of people who pitch having their own thing as the blanket definition of happiness and success. Like it or not, what you consume online will linger in your subconscious.  These two types of strangers online molded some of my thinking when I thought I was supposed to be my own boss.

Type 1) The Parrots

In Austin Kleon’s Steal Like An Artist you're encouraged to copy your heroes' work to use it as a springboard to find your own style.

These are people who are parroting what they hear but don't yet have enough life experience to form a more personally rooted opinion. Don’t we all at some point in life imitate and emulate things we hear and think we should be?

And as adults, this doesn’t stop as long as we keep our minds open to learning.

Part of growth and self-discovery is imitation. When you don’t know anything about who you are and what you want you pull from sources you think are a model of what you might want to become. You give it a “test drive” to see how it feels.

Some things you test you outgrow, others you immediately dislike, and others you keep for the long run. It’s part of the process of learning.

And in an increasingly social media-heavy world, we’re all just growing up, making mistakes, and learning from them in public. These days it’s normal to document everything we do and hold it as truth in whatever chapter of life we’re in. This includes repeating things you see people you respect say.

Now, there’s nothing generally wrong with documenting life publicly.

The challenge is it’s hard to quickly decipher who’s parroting and who walks the walk when you're rapidly scrolling through social media feeds. Although we know follower count isn’t an indicator of the wealth of knowledge it’s hard to keep the rational mind unswayed by popularity metrics.

Type 2) The Questionable Coaches

There are coaches who have the experience and track record to actually help guide someone’s development. I’ve worked with them myself and appreciated them for their radical transparency and honesty.

But then there are more beginner online coaches who coach coaches that coach coaches who want to coach coaches that coach newer coaches on living their best life as 6-figure coaches who coach 5-figure coaches that coach 3-figure month coaches that coach aspiring coaches who just finished a 3-month coaching accelerator program on living your best most aligned authentic life being your own boss.

Many of them often don't have enough experience to guide others. They recently "graduated" from another coach's mastermind full of inspirational quotes in a slack “community” and might also be “parrots”.

I don’t think the majority of them mean any harm in terms of ripping you off. They’re at the very start of their professional lives figuring out what that’s supposed to look and feel like.
Being new means being in a place of intellectual vulnerability because you’re in a constant state of “I don’t know”. Even though none of us are omniscient, being a beginner is the type of “I don’t know” where you haven’t experienced enough trial and error to have a sense of who you are and where to poke and prod at next.

As humans, our survival instinct means we naturally tend to avoid things that put our survival at risk. Many “bad” coaches were in a place in life where the hope of gaining clarity, financial prosperity, and a sense of purpose through a program seemed like a no-brainer.

Why not avoid being a mindless minion of the 9-to-5 when you can invest into your future self to be your own boss who calls the shots?

The logic these types of coaches seem to follow is:

  • The 9 to 5 = misery, work for some evil company, it's a wrong thing to desire, no control of your time
  • Entrepreneurship = financial freedom, happiness, report to nobody, a wealth of time

I see this mainly on Instagram where flawless feeds promise you that you too can “easily” attain a luxurious laptop lifestyle for a few monthly payments. Success is marketed as simple. Your hand will be held.

Yet there is never a mention of how truly difficult it is to be a successful business owner and then scale that business because that’s not “sexy”. Nobody tells you how most entrepreneurs fail because the story of rosiness, rainbows, and simplicity sells better.

I believe there are a lot of people who are scared and buy bad coaching programs because they don’t view the process of being a beginner and making mistakes as a good and necessary step to gain precious self-insight.

Maybe you are an entrepreneur, maybe you’re not.
But to know yourself and grow is to challenge your thinking.

Why I chose entrepreneurship at first

For a long time, I was the sole income generator in my household as my husband awaited permission to legally work in the US.

I needed to supplement my low income at the time from my social media job running content for Chima–a Brazilian steakhouse and national restaurant chain. I made $15 per hour and worked 8 to 16 hours per week making me $480 to $960 per month of income.

So I started a dog sitting side business from my family’s home out of desperation but also out of curiosity to learn what I couldn’t on the job.

With my dog sitting side hustle I ended up making about 5 times more money than my marketing job and spent anywhere from $50 to $100/mo on marketing and business expenses. I had to hire help and expand my services into a neighboring city.

It was my first taste of entrepreneurship. But it didn't last more than about 1.5 years because:

  1. I didn’t really view myself as a dog business entrepreneur
  2. I ran the business from my parent’s home
  3. I got a full-time marketing job

We had to find somewhere else to live because we were temporarily living with my parents at the time.
You'd think finally working in your industry would give you:

  • sufficient funds to pay for bills like transportation, phone bill, water, etc
  • a livable wage to live somewhere safe
  • enough budget to buy groceries
  • access to basic health care

But no.

I couldn’t afford our own place so we rented a room from someone who turned out to be a crazy roommate. I didn’t have the luxury of time or money to find a better situation. I just had to take what I had and make the best of a bad situation.

It was such a dark time for me. I was always scared in my own home with strange people showing up at all hours of the day, constant screaming, fights breaking out outside my room, fists pounding on the main entrance at 6 AM, and what turned out to be a super machista older man as a housemate.

I found my escape on my phone and my laptop.

At least through my content, I could connect with people I liked. But there was also the content that promised me a better life.

I had a full-time job but still my salary wasn’t high enough to afford me some basic things that would aid in my mental peace and comfort. While money doesn’t always buy happiness, if you have very little in life then money can afford you basic things that will affect your happiness (food, shelter, education, safety, etc).

I'm a fighter but sometimes even the strongest get tired of ALWAYS fighting. And because I was vulnerable and in a dark place in every area of my life except my marriage, the promise of becoming your own boss through an online business felt like a sweet taste of a better life.

Quitting with no plan in December 2018

In December 2018, when my husband finally was able to work and got a great job in a big tech company, I quit my job. No plan. Nothing.

In retrospect, it was irresponsible and inconsiderate. I wouldn't change it though because thanks to that move great things were put in motion.

At the time, I was thinking selfishly.

I was so fed up with life, exhausted from carrying us on my back, and sacrificing my happiness because I couldn't afford the luxury of exploring. I felt like it was my turn to shoot my own shot.

I'm not angry at him.

I was angry at the reality of the situation that we couldn't live properly, much less save a single penny on my pathetic salary. When I look back, I think my mind was in such a dark place I couldn’t think rationally. I was tired of doing what I was “supposed to” and just wanted to be like FUCK IT, IT’S TIME TO DO ME!!!!

So I did.

I pursued entrepreneurship to experience all the things I felt I hadn't had a chance to try. I wanted different marketing gigs and for different industries. I didn’t have a financial goal. I felt like that muddied the deeper questions.

My goal was to gain insight into what I like and want to do more of so my vision for happiness as a professional would become less blurry.

I worked with everyone from designing content for interior designers to businesses who needed consulting when it came to organic social media marketing.

The Moment I Questioned Entrepreneurship…Again

In January 2020–a year after I started experimenting with being on my own–I came across VEED.

I was their customer. I needed help figuring something out on the tool for some client work. I ended up talking to customer service but they couldn't figure out my problem so I hopped on a Google hangout with Sabba, VEED's founder.

Basically, he thought my content was cool after looking at what I was making with VEED and on my personal social media pages. So I pitched working together to him.

The following week I signed VEED onto a 3-month service agreement.
The experience was eye-opening. Even though I was drastically undercharging for my services ($1,950 per month for blogs, email, social media management, content creation, landing page copy, etc) I felt in my gut it was a wise move to invest my time into VEED. I can’t really explain it besides it just felt right.

Originally, I had set out to try things. I wanted to find happiness and fulfillment as a professional. I had no idea what exactly it was supposed to look or feel like.

Ever question if you truly want the things you want or if it's just society and good marketing putting desires you should have in your head?

I think that was the case for me with entrepreneurship. It sounded great in theory but in actuality, it just wasn't for me. Maybe in another chapter of my life yeaaaars from now I'll explore having my own thing again but for now–I'm where I want and need to be.

With VEED the connection was natural.

🧠 I loved the experience.
💿 I loved the product.
🙋🏽‍♀  I loved the people.
💖 I loved the vision.

I had so many horrible jobs before I thought the problem was the 9 to 5. But really the problem was I didn't know how to find a good fit for me and was complacent.
In my 2nd month of the service agreement, Sabba was asking me to join full-time. And by the end of the 3rd month, I realized it was what I wanted and needed.

What held me back from committing to freelance to full-time switch for VEED?

I set out on this journey after being in a really dark place I never want to go back to ever again.

  • I thought entrepreneurship was the answer.
  • I’d built an audience online.
  • How could I back out when my audience was watching me? What will they think?

And as I further dove into that train of thought I snapped out of it. It's not their life, it's MINE. Let 'em think what they want.

The real questions were…

If I join a company like VEED will I feel undoubtedly connected to this path and all it symbolizes?

In the 3 months I had VEED as a client I was more fulfilled and excited than I have ever been in my career. I felt appreciated and free to do my best work because I was trusted and never micromanaged.

What can I expect to earn so I'm no longer financially unstable and unable to invest in my future?

Sabba was extremely transparent with me when we discussed money. I'm happy with what I received to begin with, my pay increases so far, and the potential to earn more as I hit more goals and the company continues to mature.

When I envision letting go of VEED would I be filled with regret if I turned this opportunity down?

Yes. I couldn’t picture myself feeling good about letting VEED move on without me. I enjoyed having them as a client and wanted to continue being a part of what we’re building.

What do I have to lose if I say yes? What do I have to gain?

I couldn’t really come up with anything in terms of what I had to lose. Getting screwed over wasn’t something I felt either of the co-founders would do.

To be honest, I was constantly impressed by how in the loop I was about the company.In terms of gains I knew I’d gain valuable experience and build an impressive track record but also I’d have so much fun in the process.

Yes, there’s stress. But it’s the good kind when you do things that you enjoy doing.

What does my gut say?

It was a really loud yes for me!

And so I joined.
It’s about to be 2 years since I started working with VEED (I started on January 27th, 2020). I can confidently say I don't regret this bold bet I made for myself.

  • I'm part of something incredible and able to make a dent in a space that matters to me – content!
  • I get to build my personal brand alongside theirs
  • I get to work with really smart people
  • I learn new things
  • It challenges me

Success is not entrepreneurship.
Wellll…it can be if that's what you want.

But at the end of the day, we all just want happiness. That's the primary goal and all our other goals stem from this raw general sentiment.

How YOUR happiness and purpose looks is up to you. These definitions may also evolve with you into something else entirely!

Although I’m no longer attracted to building my own business, I don’t discard the possibility that years from now that might be a good fit for me. I don’t know contextual details from a future chapter of my life that might shape my wants and needs.

Now I love VEED but I'm not saying VEED is my purpose, happiness, and definition of who I am.

VEED is a by-product of my deepened self-awareness. I would've never found the right job–be it VEED or anything that comes next–had I not taken the time to explore things I'm curious about and challenge my views.

The lessons I learned

1) Embrace curiosity, action, and learning from mistakes so things can gradually become clearer.

You can't always expect to have a crystal clear vision of what your path is supposed to look like.

The most common fear I notice from people who hate their jobs is they're scared to do something different. And why? Because of how they will be perceived by total strangers and by those they know. Many of them are still in their 20's yet think they're too old to change their minds and try something else.

I know it's easier said than done. But think of it like ripping off a band-aid and having to blindly trust the pain from ripping it off will subside. You need to have more faith in yourself and welcome taking a wrong turn.

Mistakes are lessons but failure is when we don't listen deeply enough to the mistakes to turn them into a lesson.

And yes, others will always judge you. Some will judge you through their own biased lens that projects their own failures onto others. Their view of whats possible and how things should be done is shaped by their individual truths developed from their own experiences.

Go live your own life and make some mistakes of your own to get some wins under your belt.

2) Prepare to quit what doesn't serve you faster when possible.

Your resume can matter but, generally speaking, it isn't as important as some people make it out to be. You'll be miserable if you live your life for the optics of looking reliable by being somewhere you hate longer than you need to.

I wouldn't know a great opportunity for me now if I hadn't had really shitty jobs in the past and left them as soon as possible.

I understand that staying somewhere for a long time might look great on paper. But personally, I can't see how it's wise to invest time I'll NEVER get back into something I don't want.

3) When you're an intern or entry-level, the goal isn't to get a massive payday in your first job.

You need to be obsessed with finding and creating opportunities to learn the things that will lead you to things that are not only more financially lucrative but feed your soul. Learn about what you like or don't like. Collect those personal insights.

I'm not saying to not aim high from day 1 or to go work for someone that'll pay you shit and not teach you shit.

There's lots of demand and little supply. You can't let ego cloud your judgment.It was so hard for me (and others too) to find my first job ever when I had zero marketing experience. I applied to hundreds of jobs and only got like 2-3 calls back.

Sometimes, it's even possible to create our own opportunities to share what we can do. For example, with my social media career, I started my Instagram @dianagetssocial to show what I could do, what I know, and how I am.

Think outside the box to find ways to make noise and get the job or the client.

4) Build up your communication skills and stop expecting people to automatically "get you".

This applies to business, romantic relationships, friendship, and just overall life. If you don't communicate there will be unpleasant and avoidable surprises.

People don't always "get" content and it's our job (to a certain extent) to educate (and vet) the people who are hiring because they don't know much more than the fact they need help.

Maybe you hate the 9-to-5 because you need to learn to better vet opportunities and set expectations. I know that was my problem!

5) Information over-consumption can muffle your own thinking and development of self.

Treat the content you consume and how you consume it like a diet. There are the double-patty bacon cheeseburger and nacho cheese smothered fries of a social media account that are obviously unhealthy accounts you could stop following.

But also there's such thing as too much of a good thing.

You don't need to follow 50+ marketers. Sometimes following too many voices makes our minds too loud of a place to process our own opinions without us even realizing it.

A design professor of mine in Miami, Mr. Razack, told me something along the lines of that to make good creative work we need a few guidelines to challenge our thinking. But if you have no guides there's no clear purpose and if you have too many you will paralyze the creative mind by putting it into a box.

Follow whatever you need to stimulate your mind without over-stimulating it either to the point of information paralysis.

P.S. We're hiring. Apply to jobs at VEED

If you enjoyed reading this you will probably love my growing collection of 15 lessons to be a well-paid and happier content creator.

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