
Career advice is often soft and touchy-feely which is why it doesn’t work. Most of the advice is not delivered in a way that smacks you in the face and tells you to “Wake the hell up, Sonny Jim.”
Rock bottom in your career can happen in a flash before you’ve had time to even understand what the hell is going on. Before you know it, you’re looking at your bank balance go backward and doing cartwheels in the process, and wondering what you’re going to do.
I’ve been here more times than I’d like to admit. There are a few things that I wish a mentor, friend, colleague or even stranger said to me that would have been very useful to me during this period of suckiness.
If I was to take my two rock bottom career moments of the last ten years, bottle them up in one of those message-in-a-bottle moments, and put them into the ocean, and send them to you on the other side of the world so that you open the bottle, read the piece of paper, and go “Yes that’s what I needed to hear during this shitty time in my career!” this is how it would go — Timmy D style.
1. Follow up like a German Shepard
There’s no point ‘trying’ without following up. Be like that cute, fluffy, German Shepard that pretends it hasn’t seen you each night when you get home from work and follows up with a “Woof!” as soon as you enter the lounge room — who doesn’t love a German Shepard.
- Ring the recruiter 354 times to follow up if you have to
- Apply for that job ad 250 times
- Message that hiring manager on LinkedIn 29 times in a month
I remember speaking with a talent acquisition professional (that’s Timmy’s corporate voice) who I was introduced to by a stranger on LinkedIn that I’d contacted for an intro. She said, “Ahhh, we’ve seen your application lots of times already.”
That’s the best thing you can possibly hear. It means you follow up which translates to two things: you are not going to give up, and you care.
Don’t let wussies tell you that following up makes you look bad or that you look desperate. You don’t. If you really want to be the Gary Vee, real-life version of a hustler, FOLLOW UP.
Who cares what they say. Get rejected. Ask again. Get ghosted 123 times.
Just don’t ever stop following up. Follow up is the action associated with being determined and that’s what people will see when you do it. Determination is sexy as hell to anyone that knows their stuff.
2. Your gut is probably right
Rock bottom is tough and getting off the bottom of Banes dark jail cell from The Dark Knight Movie is going to require you to make some decisions.

Image Credit: DC entertainment/ Warner Bros
Logic and data in these moments is not always going to be helpful. Sometimes you need something much more powerful: your gut.
If it feels wrong, it probably is.
If you are being asked to make a decision quickly, run.
If the idea of career change that is being sold to you appears in your mind as an image of a slave labor camp from the early 1900s, it’s probably not right for you.
When you need to find that extra
something to make a decision and you are stuck on the fence — even with
all the data, references, online reviews, phone- a-friends and
interviews — resort to your gut as the last part of the process.
Are
you jazzed up when you think of the idea that is going to take your
career out of the slums and back to living like the Prince Of Bel Air?
3. In-person over email or phone
God this one pains me. You cannot deliver emotion, passion, excitement, rawness or authenticity effectively unless you are doing it in-person. If your career is still in rock bottom then there’s a good chance that you are saying yes to Skype calls, Blue Jeans, Red Jeans, Zoom ya lader, phone calls and conversations via email. DON’T DO IT.
Whatever it takes, aim for face-to-face.
It’s easy for someone to reject you via an email or video call, whereas it is much harder to do face-to-face. People buy into who you are and your story much more when they can see that face of yours, that smile, those swagger moves you got, your facial expressions, the variety in the tone of your voice, and most of all, when they can look into your eyes. (Okay let’s not go all Titanic love scene just yet).

Image Credit: Shutterstock
There is a sense of authenticity that comes from eye contact which can’t be broken easily the way it can by a 200-word email that no one cares about.
4. Say ‘thank you’ like a boss
During a rock bottom moment in your career, there will be these beautiful caped crusaders who will help you for no reason at all. Sometimes they’ll do it right in front of you and other times they’ll do it behind closed doors like the FBI.
It’s like what your Grandma told you: “Say please and thank you!”
The old girl wasn’t wrong when she told you this as a child. Manners go a helluva long way because most people leave them at home on the kitchen bench with the photos of their children that sit idle on the fridge with a KFC Fridge Magnet.
During my various career challenges, there have been many awesome folks who I’ve high-fived and said thank you to. When someone helps you in your career, they are often saying (without realizing) “He/she is a good person worth chatting to or helping.”
That’s a big risk for someone to take and you acknowledging that and perhaps showing some gratitude could be the difference between making it out alive and being stuck in career quicksand for the rest of your working days.
5. Don’t take a dump on everyone
(Attention: Internet trolls, step away from the vehicle, drop the dislike button, put your hands on the roof of the car, reframe from swearing, don’t get angry at my selfies and #humblelife and relax for a moment before you go crazy at this point).
You got fired. You had a bad boss. You got made redundant.
Yeah, yeah, yeah…stop your complaining because you are taking a dump on everyone you meet and this will not fix your career problem. Implement that overused 80/20 formula if you have to.
20% of time spent talking about the not-so-good part of where you are at.
80% talking about solutions, positive stuff and not complaining.
Got it, amigo? We don’t want to be covered in the leftover brown stuff from your failed career experiments because it, frankly, is disgusting and unpleasant.
6. Use real examples to convince people
I know you think you are the best at sales in the world. But guess what? No one freaking believes you. Everything you say when your career hits rock bottom needs to be backed up with evidence.
Get crystal clear on tangible things you’ve done in your career. Put numbers in front and behind these achievements. Do the Career Hokey Pokey and turn around, because that’s what it’s all about.
This one has been a game changer for me during my rock bottom career moments. When someone asks me to show them I know about marketing, I point to more than 1000+ blog posts, millions of views on LinkedIn, awards, startup successes using SEO and any other concrete evidence I can produce.

Image Credit: Unsplash
You are probably not a good blogger if you’ve written one article in your life.
You probably won’t take a company’s sales to the moon and back if you have never hit a sales target in your life.
You are probably not a people leader if I can’t talk to a single person who has worked for you and can tell me why you are good.
7. Enjoy the sweet taste of silence
What do I mean? Most people don’t care that your career is in the dumpster, buddy. Through these challenging times, there will be lots of silence.
Who are you again?
What email?
Don’t know that person?
And no reply to the text message from the dude you worked with for 9 years.
You are going to talk with recruiters, smash the interview and then hear nothing. You will have a final interview with a hiring manager and then be ghosted and never know if that fart you let out in the interview was what stopped you from getting the gig.
The taste of silence is deliciously sweet because it will make you humble as fuck, grateful, at peace, and more determined than a greyhound chasing a piece of meat on a moving stick while the punters bet on who is going to win.
Silence will be everywhere during this career low point. You’ll never know where the next gap of silence will come from and that’s okay. People have their own stuff to worry about and that’s why you gotta own this career problem yourself amigo.
Let the silence piss you off.
Let the silence show you what you’re made of.
Let the silence take you from rock bottom to back on top.
All Rights Reserved for Tim Denning
