Welcome to Red Flag Chronicles — Chapter 1: I was supposed to be a lawyer

The day I took this photo feels like a totally different person…

IT WAS THE SUITS TO BE HONEST…

Many are surprised to find out that my first job wasn’t working for a startup — I graduated with every intention of becoming an attorney. It was the half baked master plan that I wrote out my senior year in a state of panic because everyone around me seemed to have some life plan and mine…well…didn’t exist.

So, I changed it. Law school it is! At the time I was in an Entertainment Law class and honestly, it all seemed to make sense.

In full transparency, I just liked the drama of Entertainment Law which will be felt throughout my journey at large — trust me, it’ll all make sense and the pieces will fall into place. 21 year old me didn’t know it at the time but the seasoned 32 year old is fully aware of how the this was a critical stepping stone, just interrupted incorrectly.

It took me about 3 weeks working as a Legal Intern (associate, entry level, underpaid, all the same) to realize that law was absolutely not for me. However, it isn’t all that settling to realize that something you thought would be forever doesn’t actually pass the 5 minuet mark.

It was honestly the suits. I couldn’t get behind the suits. To this day, I don’t own a suit.

My first day on the job started with a partner, not even introducing themselves, spouting off a bunch of todos for cases and court filings they needed ‘immediately’. Everything was needed immediately. Conceptually, I understood that legal matters are critical but not everything can be immediately solved — it was as if they set a tone of “you can’t do all I’m asking and I’m fully aware but I’m going to ask anyway”. I also saw a co-worker crying in the bathroom that very same day. While I hadn’t worked in too many places outside of restaurants at this point in my career, I was very aware that seeing people crying in the bathroom is a pretty good indication of the type of culture created. It wasn’t the last time I’d see it; to be honest, it happened weekly and the one time it was me, I knew that this wasn’t for me. This kind of place wasn’t where I wanted to spend the next 30 years, law degree be damned.

Spoiler alert — the crying at work? Yea, you’ll see and hear about it again — it’s one of the largest red flags I have experienced.

But on the flip side, my introduction to the concept of ‘office work’ started here — at a law firm with little ole me trying to navigate life as an adult and the complexities of spending most of my day with ‘co-workers’. Let me be honest here, the group of people I spent my first career stint with taught me a lot about the concept of how to navigate an office and office based relationships.

People weren’t your friends.

People would do what was needed to ensure they were seen in a good light.

People would do what was necessary to move ahead.

In contrast, people would also support you endlessly if you were on the right side of office politics. I wouldn’t say that I understood the concept of ‘red flags’ in my first career stint because at the time I had no idea that these things were ‘red flags’; looking back, however, I learned more here than anywhere and didn’t realize it until 10 years later.

I wouldn’t say it was all bad, I do appreciate what I learned; law is one of the things that can create either a solid foundation or a swamp of quicksand for your business. I have always been comfortable with legal documents; I have zero reaction when someone threatens legal action or calling their attorney; I don’t flinch when I’m asked to review or provide redlines to a major contract; I’m not intimated talking to anyone else’s attorney. Maybe it’s false confidence, but the emotional battlefield that law created set me up for endless success in future emotionally taxing roles. Maybe that’s not a “win” for most people but running your own business or helping build someone else’s is a true rollercoaster of emotions day to day and my beginning ground of training for this happened at this law firm.

You’re probably asking yourself:

Why is this part important?

To put it simply, foundation is important in anything you do. It took me a long time to realize, while law wasn’t in my long term story, this role at this firm was a true foundation in navigating my career and setting the scene for determining what ‘red flags’ were and meant to me.

The basis of this is to write and share my experiences after 11 years in startup ventures; everything from fitness to real estate, I’ve seen and gone through more than most, and I have learned the lessons that live in my head should be shared with others.

And that is what I plan to do.

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Brandi Jackson - Business & Leadership Coach

Career and life lessons from one serial startup operator to another. After working for startups for the past 10 years, it is safe to say I’ve seen it all.