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Crush your entrepreneurial funk in eight easy steps

June 15, 2016


8 easy ways to stop the self-hate that plagues solopreneurs


The entrepreneurial funk. That horrid feeling that you are a worthless piece of crap. It happens to all of us. At every stage of business. It comes and goes and comes back again, even after the first few years of business. Even when other people think you’re an expert!

You can be feeling good and making strides when all of a sudden the little devil on your shoulder starts whispering that you’re not all that. The voice gets louder and louder until all of a sudden it completely overtakes you. You start to realize that you’re a complete phony. You have no business trying to build this business. You’re not qualified. No one really wants what you’re selling and everybody else is better than you.

Sound familiar?

If you’re anything like me, you will try to break through by getting super organized and updating every client project, sending them a barrage of ideas and notes and then biting the inside of your cheek because they haven’t responded for thirty minutes. Why should they? You’re completely crap at your job and they’re probably sitting around a conference table right now laughing at your ridiculous ideas.


The funk I’m talking about is a kind of entrepreneurial depression. It can last for a few days or longer, but it is completely normal. It’s the suckiest part of running a business, whether you are a freelancer, a small business owner or even the owner of a large business (at that stage, it’s usually your employee hassles that make you wonder if it’s all worth the bother).

“When everything seems to be going against you, remember that the airplane takes off against the wind, not with it.” Henry Ford, founder of Ford Motor Company.

But, there are ways to stop the funk from creeping in and ways to shake it off when it’s already all over you.

How do I know these ways work?

I’ve been in business for six years and I’ve made it through several episodes of doubt and self-loathing, both in good times and slow times. As I write, I’m in the midst of working myself out of the latest rut.

Here’s are eight ways you can dump the funk:

1. Note when it came on

Recognizing what brings on the funk, can help you to nip it in the bud next time.

Most businesses (including solopreneurs and freelancers) go through windfalls and droughts. There never seems to be a steady time. For me, when the drought hits is when the doubt creeps in. Two weeks ago I was recommended for five jobs in one week. Given that my sign-on rate is high, I felt great! I thought we would be signing at least two new clients in one week! None of the contracts were signed. That’s when I started to wonder if I’d lost my edge.

2. List Your Accomplishments

Just knowing when the doubts started isn’t enough. Before I try to crush the funk, I do something that could be considered very hokey. I write down all of my doubts. And then I answer them.

For example:

“You’re not qualified.”

“Actually, I am. I am very well qualified. I have a BA in Journalism and an MA in Rhetoric. I have been doing this for nearly 20 years and I’ve had a lot of great success.”

3. Get out.

Go out to lunch, play tennis with a friend, meet a colleague for drinks, go to a networking event. Do all of these. Part of the funk is usually a kind of obsession over what you said, or what you did, and reading into it way too much. It’s kind of like being a teenager and calling someone you like.

So, go out. But, go out to more than one thing so you don’t just add a lunch meeting to the list of things to obsess over.

4. Change the scenery

A watched pot never boils, just like a blank screen doesn’t miraculously fill up with words, and emails/ phone calls don’t come in until you’re not looking.

Walk away from your desk and try working on something somewhere else. Go to a coffee shop, the conference room, the library, the beach… And don’t stress so much about the bother of moving: the noise around you or the files you don’t have with you. Work on one thing, keep it simple and be open to new ideas that come from listening to the noise or working without the files.

If you don’t know what to work on, try this: Think back to why you started the business in the first place. What did you want it to be? What can you do right now to go towards that goal that doesn’t require input from someone else? Is it a plan? Can you draw up a flowchart? Did you want to write more? Then write now!

Try working on this for an hour away from your regular desk.

5. Shake it off.

Some of you are going to hate me for this one. I’m suggesting you get completely goofy. This works really well for me. One of the reasons I get the entrepreneurial funk in the first place is because I worry about not being taken seriously. So, by getting goofy you are giving yourself an easy way out. It’s okay to not be serious. In fact, being goofy has shown to lead to creativity.

“I try to sing in the morning. It’s hard both to sing and to maintain a grouchy mood…” Gretchen Rubin

And what right do you have to be that serious, anyway? I don’t know about you, but I’m not going to be the one curing cancer today. I’m just a mother squirrel trying to get a nut. I’m NOT that important.

“It isn’t enough to think outside the box. Thinking is passive. Get used to acting outside the box.” — Tim Ferriss

Some of the ways I get goofy:

  • I listen to a pop song (not a sad or serious song) and sing it at the top of my lungs. I mean, the very top of my lungs where I’m tired after I do it. My favorites: How You Like Me Now by The Heavy, Don’t Stop Me Now by Queen
  • I find a song on Dubsmash and record myself singing it.
  • Dance like nobody’s watching. Not delicate dancing. Ridiculous and sweaty dancing.
  • Watch something funny or motivating. Set a timer for 4 minutes and watch a Ted Talk or something funny. Make sure you set your timer and never watch at your desk so that you don’t spend the rest of your day watching TV clips. My favorites are Sports Night, Newsroom and West Wing clips.

6. Just keep swimming

To borrow a phrase from Finding Nemo’s Dory, “Just Keep Swimming.”

You basically have two choices when faced with a funk: give up or keep going. There are good times and there are shit times, but if you have more good than bad, then you should keep going.

Put your head down, avoid following up with clients for a now, and just keep working. Maybe put a plan together to reach out to new potential clients, consider what you can offer, map out the necessary steps and start filling in the details.

7. Exercise

Nothing kicks me out of a bad place faster than exercise. Yesterday, I skipped a run because I thought I needed more time at the desk. I spent the day in my head beating the crap out of myself.

Today, I ran two miles and stopped half way to take notes on a great idea I had. I sleep better when I run and I work better when I sleep. For me, mountain biking or snowboarding are two of the best ways for me to feel energized and connected with my business because both require complete focus. Unfortunately, I live in Florida, so running is easier on a daily basis! Doing something that takes my brain off work and forces me to focus elsewhere clears the path for new ideas and more motivation.

8. Keep a Completed list

I find it helpful to keep a running tally of things I’ve completed. We all have our task list, but sometimes that list can be so overwhelming that it’s easy to feel deflated before you begin. Not only that but sometimes the things on my list for today are not the things I end up working on for whatever reason. So, the list of completed things makes me recognize all the accomplishments (big and small) from each day. It also helps me with client reports.

These ways work for me, but if you have any new ideas, please share. I don’t think there is enough talk about the bad side of running a business. Everybody wants to talk about how great they’re doing instead, but it’s not alway rainbows and butterflies. It’s hard. So, if you want to share the barriers that bug you, and join in on our honest conversation, please leave us a comment!

but it doesn’t have to be…







We’d love to hear from you.



  1. Goals can be dangerous for entrepreneurs. - […]  RELATED: CRUSH YOUR ENTREPRENEURIAL FUNK IN 8 SIMPLE STEPS […]

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