How To Overcome Sadness, Depression and Crippling Self-Doubt (Guest Post)

Nobody wants to talk about depression.

Everybody wants to watch inspirational TEDx videos, get pumped up off a triple espresso and a Nike commercial.

Everyone wants to talk about how great it is to be motivated, driven and happy.

Even if we’re crying inside.

In a way, I think our societal tendency to “fake the funk” has been exacerbated by social media.

Think about it. Everyone takes pictures of themselves at their best. Doing something fun, sharing an exciting moment or hugging a significant other.

We start to look at life through an Instagramed filter and sometimes…it seems like we’re the only one who’s having a bad day. This false perception that we are alone in our struggle makes us feel like it’s not ok to talk about our challenges — because, hey…nobody wants to bring other people down. It’d be better to say nothing at all than to ask for help or admit we’re lost.

Even if that’s what’s real.

So we hold it in and bottle it up. Not only is this counterproductive (you can’t solve a problem you don’t address) — but it can also be profoundly harmful and unhealthy. You can literally shorten your lifespan by holding on to stress and anguish.

Why don’t we talk more openly about things like depression and loss?

My mission at Rich20Something is to bring you material to enrich your life by helping you to launch a business you care about and be happier.

You can’t do either one of those if you’re depressed. Another thing to remember: Depression usually doesn’t mean “I’m-so-sad-I’m-going-to-kill-myself”. That’s one end, on the extreme side. Often it can just be the nagging, heavy feeling that you have no reason to get up in the morning…day after day.

Even the most positive among us go through bouts of depression. This is ok…and it’s NORMAL.

We just need the strategies to deal with it.

That’s why I’m excited and proud that my friend Robert James Collier from Practical Idealist has agreed to share this amazing guide with us.



My friend, Robert James Collier.


I’ll let Robert share his story with you — but I just wanted to note that I keep a close eye on who is telling the best stories and creating the best content all over the world. Robert’s practical, actionable material on living a better life is world-class. If you’re not getting updates from his new blog, take a second and do that now. Totally worth it.

Robert, take it away.


Okay, depression really fucking sucks.

It’s like doing everything you can, day in and day out, just to have the chance to take a positive step in the right direction.

Every day is an accumulation of all the shitty days that came before, piled onto your back like 49 contestants from the Biggest Loser, waiting for you to take them to the finish line.

The finish line, of course, is your bed. Because you can’t wait to get away from everything and everyone and just do nothing.

The last 5 months I’ve been in and out of depression. There are weeks I go without answering the phone or returning text messages from my family. I spend entire weekends on the couch. I even started watching Kourtney and Kim Take Miami—to make myself feel better… about feeling bad.

Kinda like eating a cheeseburger when you already feel like shit.

(Don’t pretend like you don’t know what I’m talking about…)

I’m all for positive thinking and reinforcement, but let’s face it… sometimes that shit doesn’t cut it. Positive thoughts alone won’t lift you up out of the crappy situation you find yourself in every day.

I wish it did. But it doesn’t.

I tried maintaining a daily workout regimen, meditating, reading, hanging out with friends, Skyping family, waking up earlier, getting more sleep, taking vitamin D pills, eating bananas, making long-term plans, developing a routine, writing down my goals, talking to my cat… you name it!

None of it worked for me.

So here I am. Still depressed on a cold, rainy day in Detroit, Michigan with nothing but gray clouds outside while my cat Celestine sits on my feet.

Did I mention I lost power in my condo? Yea, that shit just happened. Because that’s what happens when everything sucks: it just gets suckier.

Here’s what the sky looks like outside…

This is my first time being depressed for this long a time. So I’m no expert on it. But I can say with confidence that the thing that sucks about depression is that you know something is wrong with you, but you’re not sure how to fix it.

So here’s a guide to lifting yourself out of depression when you’ve tried workouts, vitamin D, meditation, (insert failed remedy here) and none of it has worked.

This worked for me and hopefully it may help you…


1. Celebrate the small wins

This, I think more than anything, will help you to deal with your depression.

There are so many days where you try to lift yourself out of your funk, only to find that 20 minutes later—whether you went to the gym to jump on that treadmill or not—you still feel like shit. It’s okay!! It’s okay to feel this way because it’s not you! But remember to celebrate the fact that you even went to the gym!

Let me give you an example…

Before this 5 month spurt, I woke up every morning at 5:30am. I jumped out of bed, drank a glass of water, and headed to the gym to start my workout by 6am. After my workout, I came home and showered by 7:15am so that I could begin meditating by 7:30am. After 30 minutes of meditation, I would take a quick nap, get ready for work, and be out of the house by 8:45am.

It may sound rigid, but it was a GREAT routine! One that made me very happy to start the day off right by completing the most important tasks of my day early!

Well throughout this depression, I’ve wanted to return to that routine. But I’ve failed and failed and failed again. Some successes thrown in there, where for a few days (5 days tops!) I woke up at 5:30am. But the successful days were sporadic and the failures FAR outnumbered the successes.

Each morning that I came even close to waking up that early, I would just turn off the alarm and go back to sleep because I wouldn’t want to get out of the bed.

And at night, I’d know that I should turn off the tv so that I could go to sleep and wake up early, but I’d punish myself for not feeling right and keep the tv on anyway (because that makes sense…). Then I’d feel like crap the next day for not waking up early like I intended. This cycle repeated itself day after day… after day.

This self-sabotaging behavior, or psychic masochism, is more common in people suffering from depression.

Finally, I realized I wasn’t going to win this battle. At least not in the way I was attacking it: as an all or nothing proposition. Instead, I would attack my morning problem in small bites.

Each morning I would try to wake up 5-15 minutes earlier the day before. But here’s the catch: I wouldn’t actually wake up… I would just celebrate the fact that I COULD’VE woken up “if I wanted to”!

Sounds crazy, right?! But it worked!

Each morning I set the alarm on my phone for 5-15 minutes earlier than I did the day before. And the next morning when it was time to wake up, I would just turn it off and decide whether or not I’d actually want to get out of bed.

99.997% of the time I’d decide to stay in bed. But I still felt good about it because I knew I could’ve woke up at that time had I wanted to!

The next day would roll around and I’d do the same. “15 minutes earlier” I’d think to myself. And I’d turn over and go back to sleep.

It’s funny, but although I didn’t actually reach my goal of waking up early like I wanted to, I felt better about coming closer to achieving my goal. Any goal!

I started applying this to other things I was having trouble with.

I would start work for projects at night that I know I needed to finish soon. Even if I spent only 15 minutes on it before I went back to doing something worthless, I’d feel like I spent 15 minutes more than I would’ve if I had otherwise gone straight to watching Kourtney argue with Scott about getting drunk and punching his fist into a mirror the night before. (This is kind of embarrassing that I know this…)

Even with typing this post, I had to decide whether to sit on my couch and… well, do nothing. Or hop on my laptop for a few minutes and bang something out.

Already I feel better!

Celebrating the small wins is the best trick I know for making yourself feel better in any situation.

Harvard psychologists agree.

Allow yourself to fret over not knocking out the big projects or to-do’s another time! For now, we’re just working on doing something.

I promise, it helps!


2. Cultivate positive self-talk


It’s unrealistic to think we can be completely free of depression, but we can learn to understand it enough to not give it total control over our lives.

Despite the fact that positive self-talk alone won’t get you out of your funk, it does help.

Remembering that your depression is a temporary state of mind and reclaiming hope that it will be alright in the end is a helpful reminder that things will get better.

Also, reminding yourself that you have so many experiences and events to look forward to in your life (traveling around the country, your wedding, spanking your children) does help to put things into perspective, although it may not totally alter how you currently feel.

Positive self-talk is a very practical method to break patterns of negative thought.

If you’re looking for a resource to guide you, check out What to Say When You Talk To Yourself by Shad Helmstetter.


3. Speak with friends, family and those you love about how you’re feeling

This is a difficult one. It’s something that I struggle with. But I find that when I turn to the people I trust most not to judge me, they show sincere interest in what’s going on with me and want to help. Even though they may not be able to, just having them listen makes me feel better.

Love is a powerful force. And knowing that those who love you truly care about the direction of your life can reinstate hope and a drive to get better.

Also, I noticed that those whose calls I didn’t want to return because I felt like I owed them something or because didn’t want to have to explain myself, they cared too.

In fact, I haven’t come across one person who I have shared what I’m going through with who doesn’t care.

People genuinely care about your situation and want you to do better.

Remember this when you’re down because it’s so easy of us to think the opposite when things are going wrong.


4. Write

Taking inventory of your life by writing down exactly what you’re thinking and feeling in that moment is one of the best tools I know for uncovering some really interesting things about yourself.

The insights you learn from your own writing can be invaluable in helping you to understand your state of mind and how you may overcome it.

The best part is that you don’t need to have a mission for your writing. No structure. No theme. No intended outcome or length. Just write.

Sometimes all it takes is a couple of words with a pen and paper (or laptop) and the rest of the words write themselves.

Write whatever messed up shit that comes up and filters from your mind to the paper. I’ve written some pretty messed up stuff. But each time I write, I learn a little more about myself.

The action of writing down everything that is trapped inside of you is a freeing event. It’s like taking a bottle of your emotions and unscrewing the top to let them out. Even when what you write is really messed up, somehow it feels better to let it out onto paper.

At times what you see on the page is flat out ugly. Other times, you may find bits of compassion, gratitude, and hope in there.

Here’s a suggestion: make writing down whatever is on your mind the last thing that you do before you go to sleep at night. Do it in a journal or moleskin notebook, so that you have all your writing in the same record book.

You don’t have to examine it. You don’t even have to read it. Just let it out and hit the lights.

You’ll feel a little better.


5. Accept the fact that you’re depressed. And try not to minimize it.

This took me a while…

For weeks and weeks I would try to pull myself out of it by trying to push through the blockade of not wanting to workout or whatever.

I kept telling myself “I’ll be fine” and trying to pull myself together—like I’d done with everything else in my life to this point—using positive self-talk and continuing to do anything that should make me feel better.

It’d move me in the right direction for a few days or even a week. Then all of the sudden, I’d be right back where I started.

Low to the ground.

I tried reaching out to a friend from middle school who posted something to Facebook about how depressed she was and how she wished things would be better. I sent her a message saying that I was going through something similar, though on a much smaller scale, and that maybe we should chat to see if we can help one another out.

She said something I’ve heard medical professionals and people who’ve experienced depression say before: “No depression is better than another. They all affect people differently, and they all suck.”

She’s right.

What she was saying to me is that what I’m going through sucks just as bad as what she is going through. There’s no ‘Scale of Shittiness’ that I can compare my pain to hers.

Not only would that be pointless, but it’d probably suck just as bad for the winner as it does the loser (“Oh, I’m not as screwed up mentally as you are, yet I still feel like crap and am complaining about it”.)

Being able to accept the fact that you’re depressed is a huge step.

It helps to eliminate that feeling of blame for not doing things which you feel like you should or for feeling the way you feel—because it’s not totally in your control.

Once you’re able to accept the fact that you’re feeling depressed (which is to say, after you’ve identified that depression is in fact what you’re experiencing), you’re able to take the necessary actions to remedy it. Whether that’s vitamin D pills, sun lamps, medication, or counseling, it should be prescribed to you by a medical professional.

Want more tips?

This is what helped me to work my way through depression. I’m not a medical professional, but I hope that what I’ve used to get through my experience with severe depression is helpful to you too.

And if you’d like more practical ideas to improve your daily life and achieve worthy goals, then you can join our free community of Practical Idealists here.

Depression sucks. And it’s not something you should feel like you have to deal with by yourself.


Your turn:

What would you add to the list? What’s one tip that you use to overcome your unhappiness? Please leave a comment below and share your thoughts.

PS: I wrote this a year ago when I was in the middle of a depression which began in the winter and laster roughly 5 months. Thank you to those who helped when when I was low to the ground…

I really appreciate your support and love you very much.


Robert James Collier writes at Practical Idealist, where he shares practical ideas to achieve worthy ideals. If you enjoyed this article, join his free newsletter. You can also find him on Twitter @RobertJCollier.




Final word from Daniel: Thanks so much for posting, Robert. I found this post particularly useful because in the entrepreneurship world, people don’t want to talk about these issues. Everyone wants to appear strong. We can’t do our best work if we’re hurting. I made fun of TEDx earlier, but I actually think this is an incredible video on overcoming depression. Worth a watch.


Oh, and wow on psychic masochism. That makes a lot of sense to me. I think that is another thing I need to read about.


I remind myself that I have gotten through it before and good mental states and experiences have ensued, but at the same time, I don't know how I can keep getting through these episodes that seem to get more severe as I get older. I am, what others tell me, a very youthful looking and seeming 48 year old woman. But there are times when I just want to die literally and feel like I have the energy of 90 year old who just feels like she's been here too long. I know hormonal changes at this point in my life is also taking it's toll. 

My big mistake, after getting off of meds and starting to feel good and able to handle a few bad days here and there much better, was moving to a place with more cloud cover for months out of the year. This spiraled me into a SAD episode. I got so desperate that I went to see a psychiatrist and she put me on Wellbutrin, Adderall, and Lamictal. All of these things have backfired on me. Now it's summer and I have another bout of the sever srpingtime/summer SAD I used to get as well. Medications simply make things worse for me or have never done enough. I've been medicated since I was about 18 or 19 years old. I've had ECT and have considered it, almost getting it the past few years. But it's so impractical, that I just don't do it.

Again, my Adderall use has backfired on me as it did a couple of years ago and now in the process of getting off of that though it helped a little with energy and depression this past winter. 

Stress is a big trigger for me and now I have to move again - back to where there was more sun and I felt at least better for more months. But honestly, I am really really tired and my brain is in such agony. 

I have an alpha-stim device coming in the mail tomorrow. I borrowed  a friends and it really helped me after just one hour. I felt good the whole next day and then the mood plunged again.

I have tried everyting - ever supplements and I do know what you mean when you exercise and then not long after, you are very down again. I know things are seriously bad when my yoga practice doesn't have the same effect anymore, though it helps me focus better than other exercise. 

Anyway, really hanging in there and giving myself reasons to hang on. There is always ECT which I had when I was just 20 years old. I was practically catatonic from depression at the time. Again, major ongoing stress was a huge trigger.  I try and learn coping skills - which I have learned to deal with stress, but having bipolar II disorder makes it really difficult to deal with major life changes - such as another big move. 

I just wanted to say, most of all that I agree with everything you posted as tips on how to get through a major depressive episode. I force myself to do at least a few productive things a day and keep up with my part-time business. Because I know that if I let everything go to hell, my chances of seriously wanting to not do this anymore at all will increase. It gives me a small measure of control - that I can still function in spite of the illness. 

Reading also helps me. It engages a different part of my brain and gives me a sense of progress, along with a major distraction from troubling thoughts. This works much better for me than watching a netflix series, though sometimes I just can't even read. I try and I just can't get into it. Too difficult to focus. 

Getting out and socializing just a bit even helps some of the time, but I have learned I have to be careful who I have in my life. Some people are just so needy and high-maintenance that I can't let them drain my energy. I also have learned lately how to stay away from disappointing people when I am more sensitive due to depression. I just disengage as best as I can. Some people just cannot be supportive and I feel rejected so I stay away. 

Thanks for these tips. It reminds me I am doing the best I can. All the best to you!


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I think that being able to take vitamins to fight depression is a great option. Without being able to have that kind of re-balance in our life it can be hard in those rough winters. That is something that I suffer from during the colder months. Thank you for sharing. 


Thank you for the article, Daniel; I definitely agree, even while maintaining a daily regime to occupy yourself, it doesn't always help. My husband has struggled with anxiety and depression for a long time, and he's still looking for solutions. One thing he might try is counseling. We've been researching different clinics in our area, and we're thinking about getting some consultations scheduled.  Thank you for the advice, Daniel; hang in there. 


I really like the tip here about opening up to family and friends about how you feel. Depression is something that a lot of us go through. It can really hurt you emotionally. Further, it can take a toll on your loved ones. The best way to deal with it is to seek help, both professional and familial. 


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Trivedi Effect

Oliver Armstrong
Oliver Armstrong

TL;DR version: SMILE, Redefine success and cut yourself some slack, You WILL succeed with the right approach.

I read this when it posted, and it was very helpful but I haven't felt able to comment until now. Last March (2013) the business I had spent 5 years building went under. It spectacularly flamed out ending a 6 year friendship, placing me $40,000 in debt, and kicking off more than a year of roller coaster depression that caused me to doubt everything about myself. A hell of a way to end my 20's, at an all time low, not at all the successful entrepreneur that was a core part of my identity.

Having just definitively come out the other side of that depression and started to launch my second business with vigor, I'd like to say thanks to Robert for writing/posting this article. It helped a lot. In case anyone else is going through a similar rough patch I would like to add a few things that have recently helped put crippling depression behind me:

1) Smile. No seriously, the muscles involved with smiling are neurologically connected with the parts of our brain that are active when we are happy. More importantly, it's a two way street. Forcing a smile will make you feel happy in the same way feeling happy will force you to smile. Now, when an unexplained bout of crushing self doubt, anxiety, and depression descends on me out of the blue, instead of day drinking and binge watching Netflix for 12 hours, I grin like an idiot for no reason until I feel better. Sometimes it takes an embarrassing 15 or 20 minutes of forcing a smile, but literally ANYTHING is better than feeling that depression for hours, days or weeks.

2) Redefine Success and cut yourself some slack. Piggy backing on Step 1 above, Redefine how you look at your successes and "failures". On a long enough timeline my business was 0% profitable = FAILURE. However, if we do a little mental gymnastics and look the individual tasks and goals we were hugely successful at almost everything we did. I solved problems that multinational corporations with revenues of hundreds of millions of dollars had failed at for years and I did it for less than they probably spend on toilet paper in the head office. That is a HUGE SUCCESS. 

Here's a dirty little secret about business and the nature of the Universe: success and failure are most often just victims to extremely random events, even on the cosmic scale. It's hard enough to overcome the vicious randomness of events outside of our control without beating yourself up about it all the time. I know. Latch onto the brilliantly successful things that you've done as a person and cut yourself some slack for not being an omnipotent meta-human.

3)You WILL succeed with the right approach. Whether it's the business you are starting, or just making it through this bout of depression, you WILL do it if you have the right criteria for accomplishing it. I think we've all heard the saying "what would you do if you knew you couldn't fail?" That's the kind of pseudo-motivational crap I expect to see in scrolling vinyl letters on a wall behind a receptionists desk in my old office (another reason to take Daniel's advice and quit your day job).

Here's why its wrong: there is no IF, and you can't fail if you don't quit. A better question is "Knowing that you can't fail, why aren't you doing the things you want?" Now to make something clear, the Universe is FAR to immense and random for us to say I want THAT and only THAT, and getting THAT is my ONLY measure of success. That's how most of us structure our goals and we set our selves up for no possible outcome but failure. I must have THAT one job, I must have THAT one girl, I must have THAT one business, I must have THAT one profit model. The people who are successful with that approach are only lucky, nothing else. 

If you are looking for one single thing in all the world it is not likely you will find it and you will be very upset by that, however, if you are looking for anything that will work for you, it will be impossible to not to find it. When you are open to all opportunities, all you have to do is keep moving forward and you are 100% guaranteed of getting there. Now that I sound like an amateur motivational speaker or a hack spiritual guru I'll wrap it up. Life is a game, but it's not a race. Just because Apple, Google, Exxon Mobile, Jim down the street, or whoever seem like their winning the race, it does NOT mean you are losing the game. My next business may not (probably will not) compete with Google, but it can still be a huge win. YOUR success and happiness is NOT a zero sum game being played on someone else's board. Oh, and since this IS Daniel's blog let me add this: test everything. Always test, test, test!

Sorry that ended up so long, I don't have my own blog :)


Thanks Daniel! I"ll check that one out. :)


Great post! I love the candidness. I've tried all those things too.

Another I'd add to the list is "Read something written by an oppressed person." Those authors can shed a new light on things and help me really remember what's important and that I'm probably getting sad or depressed about stupid shit in the grand scheme of things.


Thanks for sharing Dan and James! It's really easy to get overwhelmed with the accomplishments and positivity we see on social media.  (I try to remember that we all are creating our online persona- and just like I try to put my best and happy "self" forward, so do most people).

Tip 5 is a big one for me- the worst part about my low moments and depressed times is that I beat myself up for feeling that way. I have a lot to be thankful for- so I feel like my worries/self doubt and deprecation/etc. are unwarranted, but this criticism and guilt just perpetuates what I'm feeling.

Rich20Something moderator

@cmurphs12  totally right, Cara.

Then it becomes this weird cycle of embedded shame. Shame because of not accomplishing a goal, then that makes you depressed, then you get shame that you're depressed. It's like emotions wrapped in emotions, and it becomes so tight that it forms a knot.


@Rich20Something that's exactly how it feels! Its nice too know Im not too crazy and other people experience the same thing!


Great article, Robert. It's refreshing that someone is finally talking about depression among young entrepreneurs. It's not all rainbows, unicorns and start up funding!

Back in the fall, I was pretty depressed for about a month. I had been backed into a corner by a relative who "forced" me to do business with her. It was draining and I felt resentful. Some days, I would just stay in bed all day so I didn't have to face my business or my relative. I felt like shit, basically.

My boyfriend encouraged me to start doing things I liked as a child and get back to my creative roots. It worked MAGIC in my life. It brought the excitement and the joie de vivre back to my life and lifted me out of my funk. And the best part...I was able to turn it into an Etsy business where I am now earning a little cash on the side. 

So my tip to anyone suffering from depression would be to say "Fuck the world" for a little while and focus on your creativity and get back in touch with who you really are independently of this crazy, fast-paced world that we live in.

Sorry for the long post.

Rich20Something moderator

@GUESTxx  Totally agree here. Do you think creative pursuits have a "cathartic" effect?


Great article! Way to challenge the status quo and discuss something that is ailing so many entrepreneurs!