Riding Roller Coasters

Don’t know about you, but I’m not that good at riding roller coasters.

I’d avoided them all my life until my wife, then girlfriend, took me on one several years ago.

It was one with a nice high hill and big ol’ drop coming right out of the gate. 🎢

I screamed so hard going down that hill, my vocal chords seized in fear and no sound came out of me. Not a sound. Felt a lot of pressure in my head though!

Now I ride a roller coaster most days of my sales career. On this topic, I have words I can actually vocalize.

It’s an important topic because it’s par for the course for anyone who wants to make a life in sales.

What you see on LI/IG/TikTok is…not much

A lot of the biggest sales influencers on social media have achieved very high levels of financial success in their careers:

• One guy I get emails from once earned ~$1.6M USD in one year of work
• A former AE I follow was a top performer at 3 tech unicorns (startups valued at over $1B)
• Another influencer I like has made President’s Club 5 times in his career and he’s only 28!

Of course, social media is generally a highlight reel.

While influencers can be decent at talking about their career struggles (I appreciate those who do), what’s easily missed by following these folks is that they don’t represent the norm for salespeople.

They are the exceptions, not the rule.

We’re all on this things together

I’ve spoken with a couple of veteran salespeople lately (one of them is one of the influencers above – they’re joining me for a podcast interview next week!).

They both talked about how hard it is to sell most tech right now.

And they’re right. In Canada and the US (and probably elsewhere), it’s a tough environment for sellers.

Economists talk about interest rate changes taking full effect on an economy after about 18 months.

The Bank of Canada started its historic rate hikes in March of ’22. We’re in August of ’24 and right in the heat of that impact zone.

A lot of businesses are feeling pinched because their customer bases are pinched.

This creates plenty of the famous sales objection, “we have no budget.”

Or it’s making sales cycles so painfully long that folks can’t close deals in time to make a quota. And that’s stressful!

The roller coast for most sellers is intense right now and probably will be for a while (some guess ~1 year but who really knows?).

Job searching is also a roller coast

Applying for open roles. Making asks of strangers for informational interviews. Selling yourself through an interview process.

These are the pillars and rails of the job search roller coaster. They can be difficult experiences. Building a career is hard.

I think about my friend who applied 10 times to a big tech company before landing a role. She was rather cowardly let go at the end of her first year, shifted to contracting and then back to a full-time job in a different industry.

The bumps are there whether we choose them or they choose us.

Smoothing out the bumps

I see at least two things folks can do during volatile periods of limited success:

1. Sharpen your skills: we can almost always control what we’re focused on and how quickly we improve.

Waiting out stormy weather in your career? It’s a great opportunity to learn something new or grow your skills.

Maybe you take an improv class or learn to tell better stories so you’re more effective in interviews. Maybe you work on your cold calling so you can book more meetings when the market comes back around in your favour.

The choice here is always yours to make.

2. Never ride alone: there’s the saying that “misery loves company” – not what I’m advocating for.

Instead, we can ride our career roller coasters with others. Sharing our experiences and lessons. Listening to challenges our friends are facing. Them hearing our own.

People talk about “when the going gets tough, the tough get going.”

More concretely, to me that means the tough lean into their communities, find support, and move forward.

No one ever needs to ride their roller coasters alone.