By Donna Litt, Writer & Author

Like so many entrepreneurs I know, I geek out on solving problems. And in my books (har har*), the more creative the solution, the better.

Now, we all know that not all problems are created equal. Some really suck to have to solve, and some are thrilling to break down. Oftentimes an entrepreneur doesn’t know what type of problem she’s getting into until she’s eyeballs deep in a giant bucket full of smelly life-ruining crud. Or, as in this woman’s case, until she’s flat on her back in shock and pain because she trusted the Super Hero.

All that said, the fact remains that there are few things more satisfying to an entrepreneur than lancing a nasty problem right through the middle, and exploding its putrid contents far and wide; and there are few things more satisfying to her than having good problems to worry about.

Below are the Top Five Problems I’ve gleaned from first and secondhand experience that make this whole roller coaster existence of entrepreneurship worth it, presented in no particular order.


Few pains are more complex and lasting than the sting of failure, and figuring out how to fail gracefully is a problem that every entrepreneur tackles whether she does it willingly or not.

It’s virtually impossible to not feel personally rejected when she fails at something, and she fails often and fails hard. But if she didn’t fail often and fail hard, she’d never learn what it takes to pick herself back up and that skill, more than any other, is the one that will help her to win.

And she likes how it feels to win.

There’s never enough time

Time is our most precious resource and should never be wasted, but for some unknowable paradox of a reason, that’s so much easier said than done.


The problem of Prioritization and Optimization (sister approaches to managing the expenditure of time) is one that every entrepreneur faces day in and day out, and it’s one of those problems that never goes away. In fact, it only becomes more difficult to wrestle with as her company grows.

But growth is a forcing function for entrepreneurs to become better at time management, and while it can be brutally painful to go through the paces required to discover how best to scale resources —the most precious of all being where she spends her time— the upside is that she learns just how precious every single minute of every day, is.



No one will ever care about growing her business as much as she does, which means expecting anyone who supports her along the way to offer her same level of commitment, is pretty much insanity. And so there will always be tension between her and anyone who supports her, because as the business owner, she’s always going to give the most sh!ts. Pardon my french.

Figuring out how to be alright with that while still empowering her people to be their best, is a difficult thing to do. It’s a hard problem to solve for many reasons, not the least of which being because the solution requires ruthless prioritization of emotionally charged issues (ack!), an ongoing commitment to bettering communication (say what?), and mutual trust and respect between equals (Unicorns have dreams too, right?).

But oh man, is solving this problem worth it. Because when she begins to figure out how the People that support her (employees, family, service providers, money backers, etc.) fit together and begin to work, that’s when the real magic happens. Because the only thing better than making a her dream a reality, is sharing the experience with her people.


She will work herself to the bone, and still won’t feel successful

And the worst part about it is that she can’t blame anyone but herself for it.

As an entrepreneur, a founder, a business owner, the buck stops with her. Like a coach, the fault is hers and the success is everyone else’s to share. It sounds depressing, because it is, but it’s also rewarding. It means that at the end of even the longest and most torturous of days, she still has control (whether it feels that way or not), and while that may mean making tough decisions —like choosing to shut things down or lay people off because there’s no more money to operate— it’s still up to her to own that decision, and she can because it’s her business.

The fulfillment she gets from knowing that someone will be held accountable, from being her own boss, and from being able to make sure things are done right, is unlike anything else, and she relishes it, because it’s her business and it’s her problem.

Putting herself “out there”  

An entrepreneur is like a battery, and to succeed she must be constantly putting out positive energy. Whether that’s asking people for things, offering help with no strings attached, having to say no, having to say yes, having no idea what to say at all but needing to appear like she knows what she’s doing… She does it all, and it’s exhausting and it’s difficult, and it so often makes her feel plain old bad.

But there’s no greater indicator of entrepreneurial success than determination, and there’s nothing she finds more rewarding than being recharged because she’s earned it, and she’ll never know that feeling unless she puts herself out there, pushes her comfort zones, over and over again, until her efforts begin to recharge her battery.


About Donna Litt


Donna Litt (GroYourBiz, Kitchener-Waterloo) is a software startup monkey turned fiction writer. She’s as excited about building a business around authorship as she is about refining her craft. Her passion for exploring human behaviour via the clues we leave behind is why she specialized in archaeology at the University of Toronto, and is what drives her writing.