Hey Entrepreneur - It's Okay to Feel Like a Failure Sometimes

Hey Entrepreneur, It's OK to Feel Like a Failure Sometimes

It's okay to feel like you suck sometimes.

This as much a letter to you as it is to me - and it's something we should all talk about more. In years of reading business books, blogs, and LinkedIn posts - I never read that one powerful sentence.

It's okay to feel like you suck.

Why does no one say this? We all look so happy on Instagram, Facebook, and the like but here's the real real on running your own business or hustling in your career: there are going to be days where you feel like you just can't win.

Days where you feel like nothing you're doing is working, no one is reading what you're writing, and your failure is imminent. Buckle up if you're at the beginning, because this is normal. 

It doesn't mean you're not successful. It doesn't mean your business is failing. It doesn't mean that you are failing. It means that you're a human doing two things that will always be inherently hard: putting yourself out there and trying new things.

So let's talk about it - embrace it - and look at a few ways to make those days perhaps a smidge better.

If you're an entrepreneur, your emotional status on any given day might look something like this brilliant graphic:

The ups and downs of being an entrepreneur

Source: LinkedIn (J.D. Davids)

A friend from my time at Disney posted this to my personal Facebook wall last week. She probably had no idea how spot on/perfectly timed this was for me.

Last week was a rollercoaster. If you follow me / are friends with me on Facebook - you may have seen these three posts.

I had the biggest week ever as a speaker. I had two presentations in 24 hours, and then I was asked to do a third on 12 hours notice. It was tremendous and a total blessing.

But it's not the full story of my week. My week was a lot more like the graph- because this whole entrepreneur thing - it doesn't come with lego-style instructions. It's a lot of trial, error, faith, strength, and perseverance.

So last week, while unprecedented excitement was happening on the speaking side, I was struggling to get a new project off the ground, feeling low and frustrated in trying to help my husband find a new job, and to top it off - all week I had it on my mind that Saturday (4/16) would be the 13th anniversary of my mother passing away. Needless to say all of these things made me feel like I totally failing at life, business, and everything inbetween.

If you can relate, I want to give you three things that have helped me.

1. Realize you aren't alone.

I've wanted to write this post for years, because I feel like this is the biggest thing: to realize it's actually normal and a part of the process to feel like you're on shaky ground or that nothing is going your way.

When it's your job to create something from nothing, or make something for someone else - being difficult is the very nature of the work. Tinkering... creation... process. These things aren't clean or step-by-step. They are inherently messy. So are you. So am I.

And like Tom Hanks says in A League of Their Own, it's not supposed to be easy. If it were easy, everyone would do it.

2. Make your own "Rainy Day" File

I like to say that any small business runs on 95% confidence. So when you have a day where you don't feel particularly confident, it's rough stuff. Sometimes even your closest friend or collaborator can't help you get back to feeling motivated and like yourself.

However, what if you could step in to coach yourself through it?

You can. On a good day, make yourself a "Rainy Day" file. This might be a saved Word document or a Google Drive document (it could even be a good old manilla envelope).

Whatever your method, your instructions are simple: fill your file with all the good stuff you can find in your desk, in your house, in your inbox, and even on social media.

Did you get a great review from a client? Cut and paste it in there. How about a nice thank you note from a co-worker? Scan it or save the physical one in the folder. Were you featured on a blog or in the newspaper? Throw the link in your document and include a couple of favorite quotes.

Save it. Repeat and update.

And on your next day that you feel low, open it. Let your own accomplishments, the words of your clients, friends, family, supporters, and more becomeevidence. This is your evidence that you can do this, you are on to something, and you will continue if you simply keep going.

If you like this idea, you might also enjoy keeping a Professional Life Journal - a place / ongoing exercise to document the ups and downs we've been talking about.

3. Ask for Help and Don't Let Days Turn Into Weeks

A big thing I struggle with, especially as a "Jill of all trades" is asking for help. I like doing things myself - handling problems start to finish. Sometimes that help might be encouragement. Sometimes that help might be needing a fresh perspective.

I was lucky on Sunday. A dear friend called me during a long drive back home. We usually text and it's probably been years since we had a long phone conversation just to catch up.

Though she's not a fellow small business owner, she had so much wisdom and encouragement for me. She was a fresh perspective on everything I was going through - and oddly enough - this made her exactly the person I needed to talk to. I felt like a new person and I would have never guessed that was what I needed to push through some of the struggle.

So, ask for help, and think outside-the-box for where you get that encouragement. 

The other thing I'd say is be mindful of your feelings. Though it's super normal to struggle and doubt yourself when you are an entrepreneur, you don't want to let days turn into weeks, into months, and so on. 

If you're feeling consistently off, it may be a sign that you do need to consider making bigger changes in your business. It's also possible that you may have personal issues you need to focus on. Allow me to also note that I'm not suggesting this post is addressing depression or significant issues related to it. If you think you might be experiencing depressive feelings, I would encourage you to seek the involvement of your closest family and appropriate professionals who may be able to help.

I wanted to mention this intandem with asking for help - simply to say how important it is to let people know what's going on in your story.

The Rollercoaster Continues

Everything I've shared with you today has really helped me manage and put those rainy, sucky days in perspective. But nothing has helped so much as being transparent right here. This is because it's my hope that if you read this and feel even 1% better about the worries on your own "worry tree" - that's a win for both of us.

Is being an entrepreneur or career professional hard? Absolutely - there are lowlows, especially when you run a business.

But the beauty is that you get the other side too: the high high's. The three speaking gigs in a row. The big client. The major project coming together. The perfect chance meeting in an elevator.

So here's my wish - for me and for you. 

May your high's outweigh your low's, and when they don't, may your rainy day file be ready to tell you that one thing you need to keep going: you got this.