5 roadblocks that almost made me give up on my big idea

Yo, I’m just going to get right to it: Building a business is the most challenging adventure I’ve ever attempted. But when I decided to start my own digital marketing studio last 2016, I somehow convinced myself it would be easy. I was motivated, skilled and well-connected. That’s surely enough to overcome what I didn't know, I thought. Obviously, with the benefit of hindsight, I can chuckle at my naiveté and admit how misguided I was.

Don’t get me wrong: My determination, talent and network have definitely helped me along this uncharted path. But that alone not enough to sustain a profitable, successful business. I’m no special snowflake. My passion didn't come with permission to cut corners. I, just like everyone else who eventually figured it out, had to train for the marathon. Because entrepreneurship isn’t a sprint.

I quickly discovered the missing link. I had no clue how to start, launch or grow a business. But identifying and admitting you have a problem is 80 percent of the battle. So I did what I always do when I want something: I rolled up my sleeves, mapped out how to get the result I wanted and worked my ass off to have it turn out.

It’s a process I’m quite familiar with. It worked when I wanted to be a newspaper editor (despite being the youngest and only Black person on the masthead). It also worked when I wanted a freelance assignment to cover New York Fashion Week (despite attending college in Texas and the publication preferring a NYC-based journalist). And it worked when I wanted a job working for Eva Chen at Conde Nast’s Lucky (despite not having any magazine experience and having to take a 67 percent pay cut from my previous job).

Surely, this same formula would unlock the keys to the entrepreneurship castle. But along the way, that formula was put to the test, as I encountered several roadblocks that almost made me give up on my vision for helping recovering perfectionists start new businesses, launch products and services, and grow their brands. To list them all would demand a full day’s time and more words than this article can accommodate. So I’ve decided to focus on the top five.

And whether you have aspirations of starting your own business or buying a home or relocating to a new city, I’m sure you’ll encounter them on your path too—if you haven’t already. I invite you to use my experiences as a cautionary tale to help you hurdle these dream-blocking barricades.

1) The This-Is-Taking-Too-Long Roadblock

When I left fashion media in October 2015, I was in a bit of a twilight zone for a few months. I didn’t want to stay in media because so many of my favorite institutions seemed to be sinking fast. But I was good at what I did, which mattered since I initially didn’t want to experience the steep learning curve that came with a new industry.

But after freelancing a few months, I took a much-needed break to get clear on my next step. And through the support of a series of personal development workshops and the one-on-one attention of a life-and-success coach, I realized my next challenge would be entrepreneurship.

I wanted to combine what I loved about being a fashion editor (helping young and emerging brands get on the radars of our readers) and a corporate trainer (breaking down complex concepts into easy-to-understand principles) with modern digital marketing strategies and techniques. That way I could help other founders, creatives and consultants get paid with their big ideas.

With my newfound clarity, came an intense wave of impatience. I manufactured unrealistic timelines of when I should “arrive.” And when I missed the mark, I spent hours (and sometimes days) beating myself up over my perceived failure.

But as I mentioned earlier, this game is a won by those who train for the marathon—not the sprint. And I realized my desperation to rush to be great got in the way of the valuable lessons that I now had access to.

2) The Am-I-Really-Good-Enough Roadblock

This roadblock tends to rear its ugly head when I’m on the verge of completing a milestone. It’s that nagging voice that says, “There’s no way you can actually do what you’re about to do…”

What I realized is that up until the leap into entrepreneurship, I’d been playing it pretty safely. I lived a fabulous life—fashion shows, free stuff, my own style column in a national magazine—but to maintain the status quo meant I had to stay within my comfort zone and not rock the boat.

That’s not necessarily a bad thing. I’d dreamed my entire life of becoming a fashion editor. And I’d worked hard to put myself in a position to make it happen.

But in the process, I didn’t give myself permission to dream again. Because of the self-doubt that nagged every time I wanted to try something outside of the box.

Whenever this roadblock shows up, I remind myself not to interact with this belief like it’s a fact. Because beliefs can change. Simple as that. And instead of “Am I really good enough?” the conversation shifts to “Who you are is plenty!”

Because there’s no manual to this. Ask any entrepreneur and we’ll all tell you the same thing: We’re figuring it out as we go. And that reality is a source of grace when I’m questioning if I’m on the right path. The same is true for you too.

3) The Fake-Humble Roadblock

Has someone ever complimented you and your response was akin to, “Who me? Nah, not me…”?

For a while, that was me. I grew up thinking that it was in bad taste to accept pats on the back. So when I grew up—and in my early days of entrepreneurship—I swatted away any compliments under the guise of humility.

But my humility wasn’t genuine. Because I wanted the pats on the back. It was incredible that people acknowledged my work. Lord knows, I had the exhaustion from the late nights and early mornings to show for it.

The problem was I felt like a fraud. The early days of my business were filled with so much anxiety, stress and the self-doubt I mentioned in the previous roadblock that I didn’t think I deserved the kudos I received.

What if people knew that I felt in over my head? Or that I questioned if I should have just gone and got another fashion magazine job. Or that I would have rather been home in Texas with my family than the loneliness I experienced in New York City?

The fake humility roadblock was just a mask I wore so I could play victim to the story that I didn’t deserve the praise from my homies and contemporaries … even though I’d worked my ass off to earn it.

This roadblock is extremely common in high achievers and people of color. (You may have heard of Imposter Syndrome.)

But you’re probably wondering how it made me give up on my big idea…

My aversion to displays of confidence and feelings of phoniness made people question if they were smart doing business with By Michael Todd.

After all, if I own this studio and I’m undermining my own juice, then why would someone pay me to help them solve a nagging problem or fulfill an intense desire?

Yep, my pursuit of perfection to avoid being viewed as a failure wasn’t only costing me personally, but professionally too.

Instead of fake humility, here’s my new approach:

  • Gratitude: There won’t be a day that goes by where I won’t wish I could have a decision back. But rather than play the blame game, I’m grateful for the experience because it’s another opportunity to learn.
  • Community: I share my feelings more openly with my family and friends. They want me to win. And sometimes an outside perspective is beneficial.
  • Service: It’s much easier for me to acknowledge my achievements because they’re grounded in contribution. And that’s nothing to be ashamed of.

When people see how much I believe in By Michael Todd's community, content and products, it gives them the peace of mind to trust me. And when people trust you, they pay you. Which leads me to the next roadblock…

4) The Running-Out-Of-Money Roadblock

In my last two corporate gigs, I had an expense account, took company-funded Ubers to and from the photo studio and enjoyed meetings with complimentary drinks and meals.

Ah, talk about the good life.

Now, I’m responsible for my own expenses. Uber is a luxury. And dinner meetings demand some savvy number-crunching to make sure my head stays above water.

Cash flow is a business’ oxygen. And lack of funding can suffocate your big idea.

The issue is exacerbated if you, like me in the my business’s infancy, only have one stream of income. And if that income is dependent on clients booking you for a service? You’ll find yourself burned out before your big idea makes it to the market.

The antidote this roadblock is simple: Replicate your expertise across different platforms.

Let’s say you’re a fitness trainer and your main service is one-on-one sessions with busy professionals in their twenties and thirties.

Your additional streams of revenue could come from:

  • Digital products that show customers how to stretch before their workout and cool down after
  • Partnerships with affiliates to host live events on nutrition, mental health and fitness
  • Online courses on how to build a fitness-focused business
  • Sponsored content with like-minded brands to promote fitness and lifestyle products

And the options are virtually endless.

But the good news is you really only need two major streams to build a sustainable business model. I won’t go into too much detail here, but we can discuss them during a "Pick My Brain" session if you’re interested.

There’s an unexpected blessing with this roadblock. When you don’t have much money, you have no choice but learn how to do it all. And during this frustrating phase of trial and error, you can discover what you really love about entrepreneurship.

I had no idea I’d love digital product development as much as I do until I was responsible for my own business’.

Moral of the story: Use every roadblock to show off your determination to overcome it.

5) The Life-Keeps-Happening Roadblock

Running a business would be so simple if you could press pause on life during those high-stress moments.

You don’t need me to tell you it doesn’t work like that. Personal chaos doesn’t give a damn about our careers, right?

For me that means sandwiching apartment viewings between client meetings. And refocusing from an argument with a friend to a game-changing business opportunity. And remembering to FaceTime my niece and nephew because they don’t care about my deadlines.

The always-on nature of entrepreneurship can threaten your sanity if you’re not careful

To fight the insanity, experts tell us to find work-life balance. But that’s never worked for me. It’s too much pressure.

Instead, I suggest creating work-life harmony. When you’re creating harmony, it’s from a proactive position. There will always be tension when you’re in pursuit of balance because you feel like you’re giving up something to get something. Harmony says I get to have all aspects of the life I dream about on terms that are responsible to me and the people around me.

One last piece of advice to conquer this roadblock: Trust that what you’re made of is bigger than what you’re currently facing. The sun is always shining even if you can’t see it.


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