My route to sales was a less than typical one. Originally from the UK, I got my Bachelor’s degree in English Literature. After a brief stint in advertising, I ended up working as an English teacher. 

Teaching high school students was never the plan. In fact I actively avoided being pigeon-holed into the role and then, sure enough, I became one. The best parts of the job were brilliant. I got to discuss literature I loved, worked with some brilliantly gifted and intelligent colleagues, and had the pleasure of working with students. They kept me on my toes, made me laugh and above all, were gifted young people who inspired me.

It wasn’t all sunshine and rainbows though…

I recently shared a post on LinkedIn about my struggles with anxiety and depression whilst working in teaching and my challenges with returning to work after the holidays. That might provide some helpful context on my previous career and my mental health at that time. For this article though, I’m honing in on my switch to sales and what my first few months have been like.

Most importantly – what I’ve learned, which might help you better manage your Mental Health if you are in a new role or new to sales.

First Things First

Right off the bat, I want to make the following clear:

  • I’m not cured 
  • I still struggle with anxiety and depression, to varying degrees depending on the day
  • I’m better able to cope with both now and for that, I am very thankful

You’d be surprised by how much overlaps between sales and teaching. Anyone who has read The Challenger Sale will know why (if you haven’t, definitely put it on your to read list). I’ve been struck by how many interpersonal skills I learned in my training as a teacher, also translate to what being a good salesperson is all about: asking good questions, teaching the prospect about your product, and sharing a new way of thinking or perspective on a previously held idea or belief. 

At the ripe old age of 30 (I’m now 31), becoming an SDR isn’t the typical career move but I knew that starting in a new profession and in a new country, equated to a new beginning. I use the word beginning because, like everything in life, your career is a journey. As trite or cheesy as that sounds, seeing myself as a beginner rather than at “the bottom” has been extremely helpful. It has helped me reframe my role at my company as well as within my own mind.

The role of the SDR can often be undervalued but as one of my colleagues, Adam, puts it, we are “the engine” that keeps the company moving. I’m thankful to Adam for sharing this powerful metaphor with me in a conversation very early on. Not only are SDRs the engine of any sales organization but you, as an SDR, have an engine too. You need fuel to stay running and, more importantly, you need the right type of fuel. 

Before I get into what I learned after months one, two and three, I want to implore everyone starting out in the world of sales to remember your value both as a professional and as a person. Fuel your personal engine with kindness and compassion. As another one of my colleagues, Dustin, put it, “you couldn’t have done it without yourself”.

By Day 30 I Learnt: My Why

To be a great salesperson, you need to understand your product, your target market/audience and above all – your why.

Everlaw (the company I work for) shared Simon Sinek’s famous TED talk with me, which centers around the importance of finding that why. This was instrumental in understanding what is expected of me, and managing my own expectations. I took this philosophy and ran with it in my role and beyond. 

This meant I contributed to conversations around diversity, equity and inclusion. I signed up for the company’s (virtual) Movie Club and I put myself out there in discussions on everything from top prospects to a debate on hot dogs (sandwich – yay or nay?). I also signed up for a course our L&D team ran.

Why did I do all this? Simply because these things are all a part of my why. I care about all of these things, so why wouldn’t I get involved?

Finding your why has a far more lasting impact on your mental health though.

As mentioned in my LinkedIn post, when I was teaching, simply going to work was an enormous challenge. I couldn’t find my why and that’s because I was fumbling in a fog, trying my best (and failing) to cope with anxiety and depression. Desperately searching in that grey void made my why a mystery to me. Now having invested in my mental health and doubled down on making it my top priority, my why is much clearer. This new found clarity helps me keep my main why and source of motivation clear. It shines a light and keeps things in perspective on the days when that fog begins to roll in.

You need to keep your why top of mind when you head to work each day. It will help take the edge off the times when you don’t feel your best. When cold calls are the last thing you want to be making or writing personalized emails feel like climbing a mountain – you need to find your Why.

Hard days are common in sales, especially when you’re brand new. Take a step back, literally or metaphorically, and keep your why top of mind.

By Day 60 I Learnt: The Value of Scaffolding

In teaching there is a well known principle called scaffolding. A quick search online will inform you that “instructional scaffolding is a process through which a teacher adds supports for students in order to enhance learning and aid in the mastery of tasks.”

As a new salesperson, scaffolding comes in obvious forms such as training and enablement resources, research, data and analytics. The less obvious and far more important support comes from your colleagues. These people (should) have built a framework for success. They already know what it takes to be successful in the role and they can give you a blueprint to work from.

Since starting at Everlaw, I’ve been incredibly fortunate to have a wealth of experience to tap into. My colleagues have provided me with valuable insight into how to become an effective SDR. In addition to sharing their best sales strategies, they have also shared how I can best take care of my mental health. Colleagues have spoken to handling rejection, how to cope with the highs and inevitable lows of selling, and the challenge of fighting burnout. 

What strikes me about the salespeople in our organization, is the blend of energy, optimism and pragmatism. It’s this blend, this subtle alchemy that makes a great sales team. Yes, I am biased but I share this in the hope of raising awareness around what a sales team can and should look like.

Of course we have our bad days and we are far from perfect but remember, perfect is the enemy of good. As a team, we are committed to refining and improving on existing processes. We commit to leaving our egos at the door and whilst this is a lofty goal, it’s one that grounds us in mutual respect. The result of buying into this philosophy is the empathetic community we are able to foster and develop.

What does this mean for a rookie salesperson like me?

I’ve got people to learn from and lean on.

By Day 90 I Learnt: Patience Is A Virtue

As a self-confessed perfectionist – or as I like to put it, an aspiring imperfectionist – my first few months taught me about the importance of being patient. In my new role, I am learning about a whole new industry and a technology that is totally alien to me. A little less so now, for my colleagues reading this! 

Early on, I was desperate to hit fast forward and skip to crushing it on the phones and obliterating my quota. I had to stop and recognize why my company invested a huge amount of time and energy in training me. Being “thrown into the deep end” should be a thing of the past. I am encouraged by organizations committing to training and enablement for their new sales hires. The company ROI on this is huge and a way of ensuring long term success and lower churn rates.

In sales it’s vital to be a life-long learner because there is always more to learn. From my very limited experience so far, sales is about fine tuning processes. Each word on the phone or in an email counts. How and what you say matters. Expecting yourself to nail it all instantly is unrealistic.

I was certainly tempted to rip up my scripts and totally change my outreach strategies after my first quiet month. But again, listening to those with more experience and trusting my training meant that with a few tweaks and with more practice – I could generate better results.

Patience is a real challenge, particularly in sales. LinkedIn especially can make your first few months in sales feel overwhelming. There is a lot of humble bragging that can easily induce that nagging self doubt and anxiety about your performance.

It’s important to limit how much time you spend comparing yourself to others. Everyone is starting from a different place and no one figures it out overnight. Progress takes patience, so focus on the progress you’re making in yourself instead of the others around you. 

Key Learnings

At the risk of writing like one of the students I used to teach, I feel a conclusion is important.

For the record:

  • I don’t have everything figured out when it comes to the world of sales. I’m nearing the 6 month mark in my first sales job and I’m a long way off having it figured out.
  • Sales is an incredibly demanding profession. It’s definitely a marathon not a sprint. Be kind to yourself, as much as possible. 
  • When the going gets tough – seek help. Don’t exist in the vacuum that is your own head. We are social beings built for interaction – reach out to someone and get some support.

I’m incredibly fortunate to have supportive colleagues. From the CEO, to our VP of sales, my managers through to fellow SDRs and countless people outside the sales team, I feel comfortable speaking to them about everything from email templates to mental illness. But that’s me, that’s what I feel comfortable with and that’s how I operate.

How you move through the world of sales and your professional life might look totally different. There is no one size fits all, so I share these lessons as a way of broadening your perspective or perhaps introducing you to a new one. Success in sales can come in many forms, be yourself and hone your craft, it’s yours to own.

About the Author

Profile photo of James DeaconJames Deacon is an SDR who works at Everlaw, a legal tech company based in Oakland, California. If you’d like to connect with James you can find him on LinkedIn or Twitter.


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