Stuck: 6 Glass Ceilings Between Wannabes and Winners

Here's a guess about you.

At some point in time — maybe even right now — you've dreamed of doing something for yourself, whether as a side venture or full-time.

Second guess: you haven't been able to cash in on that dream. At least, not yet.

Third guess: you're not giving up on that dream, but you know you have some mental obstacles—some ways you're not sufficiently knowledgeable, prepared, or even mature.

One more intuition we have: you'd be much more willing to try realizing your dream if you knew it were possible. 

There's some good news. Well, it's actually bad news, but it might explain a lot: mental blocks persist because they're not clearly visible. You can't evade obstacles you can't see. And when you're dealing with a complicated idea like starting a business, most people experience "the learning curve" as a single, horribly-tangled knot of confusion.   

Fortunately, you can still evade (or even obliterate) what's in your way. This article is going to show you what the obstacles are, what thoughts commonly characterize them, and how you can begin to move beyond yourself to do bigger things. 

The odds are against me.
I could fail—and that would hurt.  

Sure, you could fail. And yes—if you failed, it'd almost certainly sting. But ask yourself something: is the worst (realistic) thing that could happen really so bad?

When people imagine the worst, they usually imagine losing three things: prestige, resources, and opportunities.

This is embarrassing. I burned a bunch of money on something that didn't work. And worse, I can't even get the time back!

Except that—in EACH case—you might have been far worse not taking the chance.

Rather than "waste time" failing hundreds of times before breaking through, you might never try and, thus, never fail—but you'd lose the hands-on experience with failure that could have led you to breakthrough.

Now, are the odds really against you? Well, we don't know your circumstances, so we won't speak for you. But the old adage is common sense: if you decide you're going to fail, you're already right.

To go one step further: the people who beat the odds are the people who are persistent and purpose-driven enough not to care about "odds."  

Who am I to think I can do this?

Let's start here: you're not alone. In fact, we'd guess most people are uncertain most of the time, especially at the beginning of undertakings like these.

Think about a famous successful person. Was that person successful... right away? Did they just wake up, flip a few switches, and start minting money? Of course not—that person probably worked really hard before they were successful.

If you put yourself in their shoes, you might realize: during all the time they spent struggling, without any of the success they have now, they probably felt the same way you feel now.

 Maybe not the exact same. Everyone's different, of course. But self-doubt, fear, and anxiety are all normal in some measure here. Anyone who pretends to be fearless, or pretends to have complete control starting out, is doing just that: pretending. So don't buy the illusion! (See also: the spotlight effect).

If your self-esteem is low enough to be debilitating, seek help, even if it's just a simple conversation with someone who cares. Things do get better if you try to change them. But otherwise—if you're just worried you're "lesser" for feeling afraid or ignorant when everyone else seems so sharp—just ride the wave and don't worry about everyone else. They're busier worrying about themselves anyway.   

I've got too much invested in my current job and lifestyle.

The economists in the room can probably explain this in better detail... BUT here's what economics teaches us about sunk costs. They're an illusion. 

We get it: it's really irritating to invest and then step away. It runs deeply against the grain. Such absolute waste, we think. I may as well have dumped the money in the toilet and flushed it. 

But that response is actually more emotional (and less rational) than we assume. The pain of sunk costs isn't purely about losing resources; it's about emotional and cognitive dissonance. For some reason, it's really hard to unwrap our brains from commitments we've already made, even if it's smartest to cut and run.

Further proof: sometimes we'll have the option to undo a commitment and choose something better, and with ZERO penalty — and we still don't take it! (Ever doubled down in an argument you knew you'd lost?)

Here's the rational way to reconcile sunk costs. Think about where you are right now and what your next options are. For just a moment, ignore any sunk costs. Just ask yourself: what can I do next, and what are the costs and benefits of those options? 

Remember: your reasons sometimes change. What made sense in the past may not make sense now. And it's very possible that, even if one option's cost is losing some investment you've made, the benefits would make it the smart choice anyway.

My partner, friends, family, and co-workers think it's a dumb idea.

This one is a tricky balance to strike.

On one hand, it's important that you hear feedback. If there are smart or well-meaning people who offer you cautions, you should listen to them. It's not smart business to get started literally right now, when you have little information, less context, and virtually zero guarantee of success. 

Let's not forget, too, that your spouse and friends and family and co-workers are (presumably) important people to you, and you to them. Don't forget that your choices affect them. 

BUT having said all of that...

If you believe in the "case" for trying something with your life, you can't expect anyone else to argue that case for you. Try to persuade them. Sometimes that's an exercise in creativity. Still, you might be surprised how receptive others can be when you explain earnestly and give them a chance to share, to compromise with you. 

Just one fair warning: if your life changes fast, don't expect all the same people to stay in it. It's normal, in the course of "changing lives," to lose some work connections and some friends. Hate to say it, but some of you will lose family. Be patient and, as you change, you might find some new connections more kindred anyway.

Things are pretty good right now.
Why give it up?

Here's another tricky one. 

On one hand: if things are legitimately good for you, why change? might be a damn fair question. Business-starting stuff is hard. A lot of people fail at it. Ask yourself if the grass just seems greener over here. 

On the other hand: deep yearnings don't disappear without resolution. You have to DO something to get the monkey off your back.

Everyone wants to "be" something cool when they grow up. But not everyone wants to do the work. Doing is the Great Filter between wannabes and their successful counterparts—because everyone thinks, but only doers get anywhere with their thoughts.

The "work" to get there is sometimes hard, but not always—and whenever you can enjoy that journey, you'll feel a new freedom and purpose that maybe you don't feel now, even if things are comfortable. 

I'd be starting without much (or any) money.

This one ain't so delicate. The world turns on money. Businesses have expenses. And if you don't have the money, you can't get the stuff you need. 

Now the cruel part: it's easier to make money (i.e. profit) if you already have money, but it's really difficult to make money if you start with none. (Ever heard the expression it's expensive to be broke?)

In return, here's the good news: never in history has it been cheaper, easier, or faster to start the average business. Business owners are necessarily resourceful people, and this is an age when the most important resource—knowledge—is both super-cheap and super-dense. Welcome to the Internet Era. 

Impossible to say how much money you'll need for YOUR business, but it's probably less than you think. We wrote an article about 5 sample businesses you could start for $500 or less; take a peek here.

Start at the beginning and make smart plays!   

Just remember this: resolving means you want to do something, but solving means you did it. Anyone can make a New Year's "resolution," but only the dedicated create solutions for themselves. 

There's a reason they say that if you want something done right, you have to do it yourself. The main reason (aside from cynicism) is this: everyone has an opinion on what's right, but only people who DO right get to brag about it.

For a long while, you might be too busy to brag. Later you'll just be proud of yourself instead—but what more could anyone want?

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