How to Survive the Business Dark Times

Sometimes, I receive an email that’s so compelling that I need to respond right away. This is one of those times.

The note said:

“I’m a freelance online copywriter. I’m busting my butt to get clients and doing all the necessary marketing (email, networking, social media, article marketing, etc.). However, I’m still not getting the results I desire, but I see my colleagues who do the same exact thing that I do, and they are making a killing.

I don’t want to sound like, ‘Woe is me,’ because that’s not me. I’m dedicated, passionate, and a fast-learner. I guess the question is, have you experienced this kind of ‘stuckness’ when you were just starting out? If so, what did you do to get past this phase? Please note, that I’m managing social media for two clients a month as well.”

Ah, I call this phase “surviving the dark times.” And yeah, it’s tough. I distinctly remember going through this about 14 years ago and feeling so frustrated that I threw a wicker chair against a wall. I knew what I wanted. I could SEE it. I just couldn’t figure out how to make the money flow.

Obviously, I pulled out of it. That doesn’t make me smarter or better. I just had a vision, and I stubbornly held on to it – and eventually, everything worked out.

You may have seen this in your own business – whether you’re a freelance writer, a small business owner, or even a partner in a corporation. You’re working mondo hours and not seeing the money you want. You’re waking up at 3 a.m. thinking about money.

And there’s a little voice inside of you whispering, “Give it up. You can’t do this. Close down and start over.”

Are you tired of hearing the “helpful” whispers?


Maybe you subscribe to a few newsletters in the hopes that they get you back “on track.” But the newsletters almost make it worse. Every headline talks about how much money everyone else (except you, of course) is making. You read inspirational stories about people who make it big within six months of opening shop.

And that little voice inside of you whispers even louder, “Forget it. You’re wrong. Other people know the secret, and you’ll never succeed.”

Then you try talking to friends or to your spouse. They try to be supportive. They really do. But when they say, “Maybe this isn’t the right time…maybe you should get a real job,” it tears you up inside. You don’t want to talk to them anymore. So you close down and give up.

And that inner voice that used to be a whisper is now a full-force 3 a.m. taunt. You’re so burned out and demotivated that it’s hard to get up in the morning, much less work.

Here’s your compassionate reality check: This process is normal. It sucks, but it’s normal. And you will go through this many, many times throughout your career.

There are some great books on this topic (The Energy of Money is a great one) but here’s my take:

Running a business – like everything else – is cyclical. Some days (or months) you’re super-creative, motivated and in the flow. Other days, you wonder why the heck you decided to go into business for yourself. Some months (or years) you can’t keep up with requests for business. Sometimes, you happily talk to phone solicitors because – darn it – it was the first call you’ve received in weeks.

There is dark, and there is light. There is super-busy, and there is super-quiet. It’s all part of the process.

Your freelance writing business will ebb and flow like the ocean. You may as well relax and enjoy it!

Plus – and this is just my opinion – most folks quit too early. They hit the dark times, and they freak out. The fear is too much. They lose too much sleep. Instead of following their passion, they do what’s “safe.”

Granted, there are times you do what you have to do to live – and there is no shame or judgment in doing that. Just know that it’s one thing to let your dream die and give up. It’s completely another to do everything you can (even if that means taking a part-time job) to keep that dream alive.

I strongly believe that we are rewarded for being passionate. When we’ve done the planning and we can see the goal on the “other side” – we will eventually get there. The trick is – and I know that this is easier said than done – stay calm, manage by facts, and take care of you.

Some positive steps that you can take right now are:

  • Take time away from your business. Seriously! It may feel like the “worst time ever” to do it, but you need the perspective. You need to be able to look at your business with fresh eyes (and a calm brain) if you want to move forward. Otherwise, you’re going to burn yourself out and involve yourself in “busywork” that doesn’t move your business forward.
  • Take a hard, hard look at your business focus. Hindsight is always 20/20 – and for me, I know that a lack of focus can decimate my business opportunities. You may be an “online writer” – but who is your target audience? Can you picture what she/he would look like? What her hopes would be? Her fears? It’s so easy to do “anything” to get money in the door that we stray away from what we really want to do (and who we really want to work with.)
  • Spend time every day with “the end in mind.” Allow yourself to feel what it would be like to work with that company you really want to work with. Or imagine writing the check that pays off that last credit card. Or finally having enough money to take a “real” vacation. Keeping that excitement and vision alive is paramount.
  • Celebrate your successes. It’s so easy to say, “Well, yeah, I’m making money – but it’s not the money I want to make.” So what? You’re making money! Congratulate yourself and pat yourself on the back. You’ll never be able to break out of your funk if you never feel “good enough” to celebrate your successes.
  • Don’t believe everything you read and hear. Although your colleagues may say that they’re “raking in the bucks,” know that it may not be true. After all, it’s very, very hard for entrepreneurs to admit that they’re losing money (in our minds, we call it “failing” – even if that’s not the case.) It’s a whole lot easier to say that things are “great” rather than admitting “Yeah, I’m feeling pretty scared.”
  • Take care of you. At the risk of sounding melodramatic, you’re all you’ve got. If you get sick from the stress, you’re going to put yourself in a worse situation. If you ignore exercise because you “don’t have time,” you’re going to feel worse and be less productive. I would watch every piece of food you put into your body and focus on high-quality meals. The better you feel physically, the better you’ll be able to handle any situation. (After typing that, I’m feeling a little guilty that I just munched the complimentary chocolate they gave me on the plane!).
  • Recognize the voices in your head. The voices telling you that you’re a failure at 3 a.m. aren’t real. It’s your fear coming back to bite you. Notice the voices. Laugh at them. Learn from them. But do not let them get to you. They are not real.
  • Know that your hard work is not in vain. At this very moment, someone may be discussing hiring you – you just don’t know it yet. Your life and financial situation can change with one phone call.
  • Get support from other entrepreneurs. My support network is comprised of search folks and local Portland business owners. I love them. I can go to them hurting and scared and frustrated and come away feeling fantastic. It helps to know that you’re not alone (and you know that you’re never alone, right?) Other people have gone through this multiple times. They survived. You will too.
  • Ignore the naysayers. They do nothing but sap your energy and make you feel bad about yourself.  If you walk away from a friend feeling drained and tired, you may want to keep that friendship “on hold” until you’re in a better spot.  You don’t have time for folks like that.
  • Finally, recognize that this is, in fact, a phase. It’s the darkness before the dawn. It’s miserable and scary and…a little bit exciting too. Once you’ve gone through this a few more times, the process does get easier. You start to recognize what’s happening and move through it a little bit faster. It doesn’t make it “fun.” Heck, I go through this phase kicking and screaming (sometimes literally!) But at least you may not take it quite so personally next time.

If you’re going through this – hang in there. Know that things will – eventually – be OK. And let me know how it’s going. We’re all in this together.

24 replies
  1. Amy C. Teeple says:

    Wow Heather. Thanks for writing this. I can definitely relate. It’s tough to stick it out when your fears are sneaking up on you.

    I strongly agree that you need to find a strong support system. This is not only good to help boost your morale, but many times it helps to have someone who can see something that you cannot – simply because you are too close. As you mentioned in a recent article, sometimes you ignore something that is so obvious and you just need someone else to point it out.

    I need to second your tip about taking care of yourself. Sometimes you can get into these cycles where you get caught up in a struggling business and you let everything else fall to the wayside. I have been there, but I know that when I force myself back into my workout routine, I really do get better focused on my work. I get a renewed energy and couldn’t we all use that!

    By the way, as long as it wasn’t your breakfast, I think it’s OK to have that piece of chocolate every once in a while. :-)

    Thanks for the post.

    • Heather says:

      Yeah, I’m really glad that I wrote this post. A bunch of folks have pinged me privately about it – they were thinking that they were the “only ones” who felt the way they did. Which is kinda sad, really – in our hyper-connected world, it’s discouraging to hear about folks feeling very, very alone. Of course, they aren’t alone…but I understand how they feel.

      Thanks for your post, Amy. And I’m really trying to not feel guilty about that piece of chocolate that was so, so good (or the croissant that I ate earlier…yum!) :)

  2. Nina says:

    Thank You Heather! I have to really work on recognizing the voices in my head. I think that’s where the main issue is. Great tips! I will bookmark this post, and use it for refrence when I’m feeling stuck. I appreciate all that you share!

    • Heather says:

      I TOTALLY understand. Those voice are MEAN. I once read that any internal “voice” that isn’t operating from a place of compassion is a voice to ignore. Easier said that done – especially at 3 a.m. (and I’m a big “wake up at 3 a.m. and stress person.) But it does put your internal voices in perspective.

      We’re all in this together – even if we’re “competitors,” we’re still people just trying to get by and enjoy a better life. If only we’d feel as comfortable sharing our fears as much as we share our successes….

      Thanks for your comment. Great to hear from you. :)

  3. George Passwater says:

    Love, love, love this post Heather. Thank you for posting it.

    I can also relate to this. It sucks, but I know I can never give up. I have heard the voices inside and out, but I don’t give in – I keep fighting. It doesn’t matter what happens, keep crawling and soon you will be up and running!

    Thanks for the this great post Heather!

  4. Claire says:

    What a lovely and inspiring post. Thank you for sharing your thoughts on the subject of tough times – you’ve covered the challenges on so many levels – how insightful!

  5. Adrian Grossett says:

    Wow – what great inspiring information – you’ve certainly been there got the T- Shirt – BUT your also educating the rest of us – to stay POSITIVE no matter what – and that is priceless information!

    Thanks keep up your good work and best of luck in your business ventures.

    • Heather says:

      Oh yes, been there, done that, got the T-shirt. Multiple T-shirts, actually. It can be super-hard to stay positive sometimes, especially when you feel like you’re the “only one” going through something (which is never true, but feels VERY true.) I’m glad that I was able to help other folks feel a little better about their situation, if only for a little bit. :)

  6. Devin Miller says:

    After a great day exploring a German forest and all of it’s beautiful fall leaves, I came home and read this. How beautifully written.

    It’s comforting to know we’re not alone – even though I sit in my house alone everyday striving and trying and writing and making lists and wondering if “it” will ever be here to validate the hours. (“It” being of course money.)

    I feel proud though that I did step away from the computer and my business today…I haven’t been so good at this lately.

    I’d been telling myself I needed a full day of fresh air for awhile, but kept messing around with “busy work”, trying to make everything happen in a day. Stepping away from the process really does offer great clarity, more energy and a “calm brain.”

    I loved this article. I’m still in the early stages of growing my business, and now Heather, you’ve inspired me to get back to work and finish my own marketing strategy and target market research right now.

    Never surrender!

    • Heather says:

      That’s the really hard thing about working alone. It’s so easy to “strive and write and make lists.” You mean to take a break – you may even schedule it in. But it’s easy to start feeling guilty and think, “I’ll take a break after I finish this. Then this. Then this.” Before you know it, you’re exhausted and stressed and miserable – and you haven’t taken the break that you promised yourself.

      GOOD FOR YOU for taking a full day for yourself. Your walk sounds lovely.

  7. Dan Walton says:

    You just brought tears to my eyes… It’s all so true. Some times are busy, some times are slow but, it all crashes out on the same beautiful beach… Thanks for being on my support team!

  8. Pamela Jones says:

    Perfect post at the perfect time. It’s just what I needed today for a pick me upper. Work’s a bit slow now; wondering what I’m doing wrong. Now I know I’ve done nothing wrong. What’s happening to me happens to all writers. Thanks, Heather. As always, you’re a jewel.

    • Heather says:


      Oh yes, it happens to all writers (and all business people as well.) I’ve been self employed most of my life and I’ve seen times of incredible financial success…and I’ve also seen the other side. :) The hardest thing to remember during a financial downturn is it isn’t personal (even if it feels very personal.) And eventually, somehow, it always works itself out.

  9. Dianne Jensen says:

    I’ve known it as feast or famine. I have a full-time gig, but live in Cali so side jobs are welcome. One freelance client has a tendency to disappear for months at a time, then come at me with 40+ hours of work within a one-week span. On top of the day job, it pushes me to the brink. Then nada again…it certainly is frustrating and makes it tough to figure out my finances, but I’ve learned to roll with it and enjoy the few times a year when I can go nuts with my money. Of course, I tend to spend it on crazy stuff like new tires for my car or sending a double payment for an old “oops” to the IRS.

  10. Teagan says:

    It constantly is amazing to me exactly how Bloggers for example your self can find enough time and also the commitment to keep on Producing great discussions your blog is excellent and one of my personal need to read blogs, I’d been more than impressed with the blog post I simply wanted to thank you and congratulations

  11. Adonna says:

    Thank you for this heart felt post. I have been self-employed for a long time and I can second every thought contained within. Feast or famine is very common in the beginning of any new venture!
    It can also be helpful for people to remember that being a freelancer also means that you are now a small business person and entrepreneur. It can be very helpful to hunt down stories of startups and small business woes. Most of the problems that they will find there are *very* similar. They can really help us to remember that we aren’t alone.

    • Heather says:

      Adonna, GREAT tip. Reading about other entrepreneurs is a great way to normalize your situation. I’m always surprised at the number of successful folks who “fail” (sometimes, quite publicly) until things really start flowing for them. It’s a good lesson that a scary situation isn’t permanent – and success is right around the corner. Thanks so much for your suggestion!

  12. Ruth says:

    This post is great and everything in it is so true.

    It’s not just for freelance writer’s it’s apt for any sole trader starting up in a new business….and when I say new, it can be the first two to three years and you still feel on a roller-coaster.

    Proper sleep patterns and eating are so important yet we so easily dismiss them as unimportant. If we have to work through the night putting a proposal together or doing mundane tasks such as dealing with rubbish emails we do it as there doesn’t seem to be enough hours in the day at times. Then there follows a period of non-productive days because we’re so dog-gone tired. And then, what happens, we beat ourselves up for being unproductive and the demotivation kicks in.

    For me, to be able to recognise these peaks and troughs in my business life is 50% of the way there. I know, if I’m tired or feeling demotivated then all I need to do is give me some me time – get some sleep, take some time out, walk with the dogs, do some housework (that’s a great motivator as it’s productive and I see instant results) and catch up with some friends. Life as it was when I had a “real” job and didn’t take the work home. I come back from this with added vigour, passion and determination and my brain is rested in order to be creative, think of ways in which I can provide added value to my existing and future clients and get the excitement going again.

    What’s also important about the “me” time is that I dump my brain. I write everything that’s floating around in my head down on paper. Often on separate ‘post-it’ notes. Often of outstanding tasks but it’s not a to-do list. One look at a list that long would prevent me from taking the needed time out. But little individual notes help me to prioritise and after my few hours or day off I can then set about picking one, two or three of these notes to work on and put them in my day book. Putting a tick through them and seeing everything done for the day is more motivating than seeing a long list which has had more stuff added than crossed off.

    Lastly, I have a business coach. This is the person I go to if I start to lose focus. She is brilliant in grounding me and finding ways of doing stuff that without getting it all out in the open, my hopes, fears, vision, goals would all just be a big mush of too much to do.

    The support network is imperative as not only can you learn so much from your peers when you communicate on an open, honest and equal basis you will not only learn a lot but you will contribute a lot too. One of the people I consider to be a queen in my industry (some may consider her to be a competitor) is way up there in my support network and with all her knowledge and experience she shares with me, I get a great sense of contribution, pleasure and feeling that it’s not a one-way street, when we spend time talking together or she calls me up to run an idea past me.

    So, I would say, don’t treat competitors as the competition. You can often find ways to help each other and often, pass overflow of work, referrals to people you know, like and trust. This keeps your clients happy too.

    Again, a great post – sorry I found it so late!

    • Heather says:

      Ruth – your comments are fantastic! Thank you! I especially liked your tip about the brain dump. I was feeling overwhelmed yesterday and created a to-do list. Turns out, my list wasn’t as bad (or as long) as I thought – and I felt much, much better.

      (And yes, unfortunately, you can still feel like you’re on a roller coaster 3 years in…)

      Thank you again – GREAT ideas and feedback!

  13. Matthew Newnham says:

    Hi Heather,

    Hmmm, 18 months after you posted this (spooky timing) and this is still every bit as timely. Thanks as ever for a value-packed post (and thread). Great marriage of head and heart…

    Best wishes from Scotland,


    P.S. Your post reminded me of that Mamas and Papas song, Dedicated To The One I Love, with the line: And the darkest hour is just before dawn…

  14. Matthew says:

    I’ve gone through a few of these dips in the past … it’s always good to know you are far from alone when you feel this way … bookmarked this article, thanks!


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