How Long Does It REALLY Take To Become “Successful”?

For a long time, I was EXTREMELY FRUSTRATED.

I was sick of being stuck in the same place, and I would have done anything to get massive results really quickly.

In fact, I thought since I was a cool, nice (albeit mildly vain) person, that I DESERVED to get that massive success. After all, who else would deserve it more than me?

As weird as it sounds, I often measured myself after rappers my age.


Drake and J. Cole

I actually don’t know why I would bother modeling my success after them. Drake and Cole are cool and all…but I don’t want to be a rapper.

I don’t desire that skill set, want to run in that circle or live that life. In terms of practical, actionable steps, our paths have literally NOTHING in common.

But society told me that’s what being young and “successful” looked like, so that’s what I wanted.

I remember actually feeling jealous of young entertainers and thinking…

“Why not me?”

“How long is this supposed to take?”

“When is my turn?”

“What do THEY have that I don’t? I’m just as special!”

Ha. Oh god, I’m cringing just reading a paraphrased quote of myself.

Much like those Facebook posts above, clearly, I didn’t “get it.”

I didn’t really see any difference between myself, and others who’d achieved notable success at my age.

Eventually I got over myself, got busy and made things happen. I hadn’t really thought about that period of my life in a while.

Until recently…

When I was scrolling through Spotify this weekend, it suddenly clicked.

I realized exactly WHY I was so dissatisfied with myself during my early 20’s.

The success timeline

Check out Drake’s album timeline…


Drake’s albums since 2009. Yes, I’m listening to “Rich Off Cocaine.” Back up off me.

I count 4 individual albums since 2009. But that doesn’t tell the whole story, does it?

If you’ve been following Drake’s career, you know that he put out Comeback Season in 2007…


Comeback Season was a really great mixtape. Production was solid.

But not so fast. Don’t forget that he also dropped Room For Improvement in 2006…


Room For Improvement

And let’s be honest…do you think that 2006 was the first time he ever picked up a microphone or got the urge to start rapping?


Even in ’04-’05 when nobody took him seriously or cared about Drake the rapper, Aubrey Graham was sharpening his skills spitting CORNY flows on daytime television for preteen girls!!!

Drake’s part starts at 0:44

Ahhhh, now it’s ALL starting to make sense.

Someone these days will look at Drake and say, “Wow, he’s so young. He’s so LUCKY!! How much work could he REALLY have put in?”

My response: OVER A DECADE of documented work, actually.

How many of us have done ANYTHING for a decade besides eat and poop at this stage in our lives?

(School doesn’t really count. You were forced to do most of that.)

So in response to the questions: “How long does it take to become successful?” and “What about ME? When is it my turn?” I suggest this — don’t get frustrated when, after trying something for a few months (or even a few years) you’re not getting the money, recognition, fame or freedom that you want.

Stop comparing yourself to the CURRENT success of other people who are your age — the Zuckerbergs and Drakes of the world.

That’s like comparing their “finishing position” to your “starting position.”

It’s not fair to you, and it’s not an accurate representation of where you are, or how far you’ve come.

Instead, compare yourself to their beginnings.

Think about Zuckerberg the first time he EVER wrote a line of code.

Was he a billionaire tech guru? No, he was a clueless beginner.

Think about the very first time Drake EVER picked up a mike.

Was he a Grammy winning rapper, with millions in the bank? No, he was a nerdy kid in the basement.

THAT’S YOUR BASELINE. Go from there.

If you’re going to judge yourself at all, judge yourself against THAT.

Now, take a deep breath and think about where you are.

Doesn’t that feel better?

Not so bad, huh?

Realize that most overnight success takes a decade of silent hustle.

And then, keep hustling.

PS — Who else can you think of that fits this description?

Who else can you think of, either in the public eye or your personal life that put in many years of hustle in the background before coming an “overnight” success?

For me, Tiger Woods also comes to mind.

One of the greatest golfers ever, sure.

But he’s been golfing since he was THREE.

Kinda makes sense, doesn’t it?

Think of someone and leave their name in the comments. 

It will help us if the whole tribe can see just how many “successful” people really put in years of work before making it.


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Love this post.


Sweetest version of "Blackbird", D! Thank you for that :)


My suggestions are Jose Bautista of the Toronoto Blue Jays or from years past, Luis Gonzalez of the Arizona Diamondbacks.  Granted they were in the big leagues but until someone changed their swing they weren't the superstars they came to be later in the careers.

-Matt O'Brien

Dan McDaniel
Dan McDaniel

Oprah Winfrey worked in the television industry for 10 years before getting her own show. At age 22, she was making only $22,000/yr. with a crappy boss that didn't like her name or the way she looked. (Oh, the irony.)

Jennifer Lopez worked as a backup dancer for years (for Janet Jackson, "In Living Color," etc.) before getting her big break. She didn't even record her first album until her late 20s. That's super late for the entertainment industry...

Dan McDaniel
Dan McDaniel

I can't help but to think point #2 was about me... after that book post last week...

Rich20Something moderator

@Dan McDaniel Hahaha, that's hilarious — especially since I debated between whether to put 19, 20 or 21.

Rest assured, it's not about you. There's even a screenshot of my own post. It's all deprecating :)


I do this A LOT. When it comes to entertainers and I look at people Rihanna and Nicki Minaj -- even people like Dawn Richard and Teyana Taylor – I always tell myself that massive success and global recognition by my age is possible. Even if that is extremely rare I end up comparing myself to just people who have achieved millionaire status by my age. Of course, most of those people are in the entertainment industry but being worth $5-8 million is a lot more reasonable than expecting to be worth $100 million by 26. It’s disheartening. It’s not a constant thing on my mind but when I allow myself to drift into what others in my age group have done by the time they’re my age, I feel behind.

At least in terms of where I wanna be. Like in comparison to the general population I’m doing GREAT for my age. Right on pace and even better in some instances. I recognize that I have a good head on my shoulders, work ethic, a few accomplishments under my belt, I’m at a great place for 25. But it somehow ALWAYS manages to dig at me how behind I am when pooled in with people I actually wanna be in league with. You ever watch that show Suits? People like Mike Ross and Racheal Zane. Young go-getters making a pretty penny, traveling, extremely successful at what they do. Those are clearly fictional characters but I just mean…it’s possible to have a reputation, exposure to the world, and a net worth in the millions by 25.

I haven’t gotten there and it sucks for me. 10 years of work for an overnight success. It wouldn’t be so bad if people were in this with me. At least I’d enjoy slaving myself out for idealism.

Rich20Something moderator

@TheAjax Is being worth $5-8 million by 26, for someone who isn't in entertainment really reasonable? 


Great read. Very much like Gladwell's 10,000 hours theory.

I'm actually closing in on almost 10 years of rapping myself--although I haven't committed to it at nearly the level of professionals. I did just do my first ever live show over the weekend though and it was so much fun, maybe I'll be on your spotify playlist someday :)

Anyway, other examples: MJ (anyone, Tyson, Jordan, Jackson...#RIPBiggie), Gates, Jobs, the list goes on!


Oh and i'm feeling your song choice on that Richer Than Rap LP. Yacht Club is my jam tho ha!


Wow, thanks Daniel. This post I really needed to see right now. Am currently writing this on my break at the day job that gives me endless grief... It's not like the work itself is bad or the people are awful (they're some of the best people to work with actually) but I just HATE this place right now cos I know I cld so so much better if I put that work in, consistently.

Cheers for the post again, sometimes you just need to hear someone else say it, to acknowledge what your feeling.

Rich20Something moderator

@FreshFaya Glad this helped :)

What's something you say to yourself to push through a tough day when you're mentally exhausted or just don't want to be there?


I'd be lying to you if I told u I was telling myself something positive to push myself to the end.of the shift.

But in my mind, I'm usually telling myself, "when you get home, just continue working on building your Internet business and you'll leave this godforsaken hamster wheel eventually"

Or I just go to one or two of those people that I work with that are blessed with an undying positive attitude and an ability to make me laugh even when I don't want to...

Even a simple response to a basic question like "how are you" to these individuals and their random answers have me rolling. I'm blessed to work with people like this when I think about it.


Great point to start a Monday off right Daniel "Colossus" DiPiazza! Haha. Having studied music myself and the musicians that inspire me, I'm going to go ahead and add pretty much any musician to the list. True, many musicians have things work out quicker than others and have the right person hear them, but either way, dedication to the art of music and grinding it out with no one listening is what has to happen first. 

This mindset/fact applies to any business or art (music tends to straddle both). 

Everyone knows the Beatles. Some people don't realize that they spent several years playing shitty clubs in Hamburg, Germany. Some nights they were booked to play the entire time. Like 10-12 hours straight. They were not yet known and had to grind it out, learn how to perform, etc. 

So yes, even the Beatles had to hustle before they became the most important band in the world. 

Key take-away from this: you have to love what you're doing first and be willing to do it for free without recognition, notoriety, etc.

Rich20Something moderator

@practicalcivilization I love that song. Let's have a "play-off."

Shoot your video and post it here. I'll shoot mine.

No doubt you'll destroy me, but it'll be fun :)


Daniel, I for one really liked your video and your singing and playing was wonderful.

Rich20Something moderator


Hmm, it's not displaying. Odd.

JESUS YOU CRUSHED ME!!! Well, well done. And you mastered the part which I haven't — that nice syncopated rhythm. VERY, VERY COOL.

Well done :)


Totally correct about the Beatles.ILiked the song "So now it's Christmas". I know that's not the title but hopefully you'll know what I'm talking about.For those not in the entertainment business why would you compare yourself to these famous people? I don't think all these comparisons are worth much-they are a waste of time. For me I had almost ten years before I became successful. I just sort of kept my head down and worked hard and I did not get lost in comparisons. Comparisons are distracting and if you are on the path of success there is no room for distractions. And keep in mind that there are many different definitions of success--it is not a one size fits all.

Daniel, very well thought out article-I am amazed that I can get some direction from your articles at this point in my life.


@Rich20Something @Macy1029 Wow! She must be very proud of you, D. Great article and excellent advice. Best to keep true to your heart's calling and not be distracted by what you think others have accomplished!

Tiffany Lee
Tiffany Lee

I love this post!!  Drake is one of my favorites and I love that you pointed out just how long he's been at this.  I've mentioned this before but another one of my favorites that comes to mind for me is Kanye West. He did a lot of behind the scenes work long before he came into the spotlight. This is a great reminder that EVERYONE started somewhere.  Especially in the world of entrepreneurs, we tend to get caught up with seeing where people are now instead of seeing the entire journey that got them there.  This is a great way to start the week.

Thanks Daniel!!

Rich20Something moderator

@Tiffany Lee Very true, T! Can you think of someone else that fits the bill of starting from the bottom? :)

Tiffany Lee
Tiffany Lee

@Rich20Something @Tiffany Lee Yes, I've recently learned about a woman named Asha Tyson who went from being homeless at 17 to "retired" by the time she was 26.  She didn't have any resources or advantages and she took a chance on getting an education and working her way up.  Then she realized she wasn't fulfilled so she quit and started working for herself.  Her story is really inspirational.  Here is a link with more info if you're interested:  


@Tiffany Lee 

"Especially in the world of entrepreneurs, we tend to get caught up with seeing where people are now instead of seeing the entire journey that got them there."

Me. I take mental snapshots of where people are at 25-27 and I really should stop doing it. It works better if you look at their journeys and note the similarities; that way, you’re almost reinforcing yourself to see that all this work and grind you’re putting in leads up to something. Not only that, each individual has their own end goal in mind. I don’t wanna be anyone else but me so while I can draw reassurance and security from the journey of others, I still have to accept that my journey is going to unfold for me in its own way at my individual pace. It’s natural. It’s something everyone has to make peace with.