R
R

RickShameless

Accounte Executive

Good Citizen
Contributor
Fire Starter

Am I in a Rut? Has This Happened to You?

Hey Y'all,


A little bit about me:

I went to University because everyone around me was, all my siblings did (I'm the youngest), my parents wanted me to, and all the other wrong reasons we go to post-secondary education with no vision. I woke up in year 2 and dropped out after. After doing some soul searching and taking advice from some people in my life, I found sales. I had no experience so where did I go? Men's Warehouse to start selling suits.


I quickly got moved up into a commissioned role after about 6 months, and finally had something to show. I quickly did a lateral move to start selling cars at a local Toyota. I was crushing it there but hated the commute and the cutthroat Ups system. So I turned to the internet to find my ideal next move. I did some research and found the description for a SaaS Account Executive. Realizing that I could work from home or a funky office, and have a territory where I wouldn't compete directly with my teammates I fell in love - but didn't have a lick of experience.


I found a posting for an SDR role and spammed the VP of Sales at the company to hire me. On my first call I got a demo, proceeded to crush all standing opportunity generation records, all in an attempt to reach my coveted Account Executive role. 5 quarters in I got promoted to Account Executive - the youngest at the company by a long shot. I had made it.


Now in my second year as an AE, I am on pace to make between 100-125k this year. I am 24, and all of my buddies are stuck in entry-level accounting/finance/bank jobs making 60k or less, taking shit from their bosses. A couple of them went on to get Master's degrees as they couldn't land these jobs with their Undergrads. I'm making more money than all my siblings and my parents. I should feel like a winner, but I don't.


Despite my achievements I'm in a constant state of imposter syndrome, I feel like I'm not progressing now after spending 3 years in SaaS, and I feel aimless. Yeah making 6 figures is great, but after taxes and stuff, it's just money. I need advice and I don't know where to turn. Hell, I felt more drive as an SDR gunning for the AE spot. I had a goal.


Has anyone hit a wall like this in their career and just felt awful about where they're at? Should I keep grinding at the same company? Should I make a lateral move to somewhere with better mentorship? Should I ask for a raise? Should I change careers? I need help from somebody who's been through this already. Could anyone connect with me offline perhaps?


🎈 Mentorship
☁️ Software Tech
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17 comments

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TechSalesQueen
Executive
5
Sr. Enterprise Account Executive
Ask yourself if this is how you want to spend the rest of your career. Ask it now. Ask it void of a need for money or proving anything to anyone in the exploration. What do YOU want for yourself that will make you feel like you remained true to your passions and to what motivates you. If it isn’t sales? Please run. Go follow your dreams. Sales doesn’t get easier. It’s perpetually stressful. I’ve made $80k in a single month and still wanted to change careers. I’m constantly the #1 rep in the country and I still don’t feel fulfilled. If you’re 24 and young and you still can go follow a passion making decent money with some grit and hard work then go do what you really want to do!! If your goal is leadership and money then stay. But I have to believe most of us want more than what we’re stuck here bitching about day in and day out. I spend every single waking minute of my free time on my side career that I’m hoping to turn into my full time job. I’ve sacrificed a lot and I appreciate the confidence and business acumen and training I’ve gotten along the last decade but if I was 24 again I’d run for my freaking life. Just some thoughts from a 34 almost 35 year old here. I wish you lots of luck either way!!! 🙌🏼
RickShameless
Good Citizen
1
Accounte Executive
Thank you so much for the encouragement. Good luck on your side career Queen! 
Diablo
Politicker
3
Sr. AE
All are anonymous so connecting offline might not be a possibility.

Listen, I see you throwing 3-4 options money, career growth, changing industry etc etc. but what is it that you want, what can bring you joy? All have been through this and going through this almost everyday but trust me you have your own answer.

Loved the fact that you had a goal (in the past), try to have one again because that will give you the direction. For some money is more important than other factors and vice-versa, but you cannot make someone else goal your goal unless you resonate with it.

Give yourself time and think...
RickShameless
Good Citizen
0
Accounte Executive
Thank you, Diablo for the thoughtful response. I guess I’m just bogged down with the choices and am frozen to indecision. Going from 125-200k sounds nice but I’m not sure how I’d get there in my current role. There’s guys doing it here for sure but they’re vets with 16 and 13 years in the bank. It’s an old company it turned 30 this year. I also don’t know if 3 years is enough to move with. <br>Feel like a first-world problems Whiney B*tch lol.
1nbatopshotfan
Politicker
3
Sales
There’s no shame in feeling like you’re in a rut. We all feel that way sometimes. What’s motivating you? Figure that out and then peg your job/career to what you’re motivated for/towards. Is it a ski house or minimal hours? Do you want to work in a field where you help people, or do you only care about money? 

I would recommend thinking long and hard and evaluating quarterly on what you want out of life and what gets you to that point. 

Keep your head up and don’t make any rash decisions. Put enough cash away that you can take time off if you need to or want to. 
RickShameless
Good Citizen
1
Accounte Executive
Thank you for the kind response and advice, NBA. Been socking money away for this exact thing. 
1nbatopshotfan
Politicker
1
Sales
No problem. Keep your head up! This has been a really difficult year + for a lot of people. It’s not shocking that you’re thinking about a change. Have you taken much time off? That could help. 
RickShameless
Good Citizen
1
Accounte Executive
Not really worth it because we have monthly targets. I think I need a month to decompress.
1nbatopshotfan
Politicker
1
Sales
Take a long weekend. Recharge where you can. No matter what the monthly number is, a day won’t kill you. Burnout will. 
FamilyTruckster
Politicker
2
Exec Director, Major Accounts
You’re young and making good money. But being dissatisfied happens. The chase (for now) is over. 

Ask your current boss if there are any projects you can help them with. Also, what do you want to do? Are there any other options at this company you’d like to pursue? What do YOU want to do*?

*I still ask myself what I want to do and I’m 35. You’ve got the world by the balls. Take some time to reflect. 
dwightyouignorantsale
Politicker
1
Account Executive
I feel this. I am the youngest rep on our team and despite being the person that is often leading trainings and get reached out to for help, I always feel like I am not to their level. There isn’t really any good advice I can give for not feeling “imposter syndrome” aside from looking at your achievements as proof of you knowing what you’re doing. I guess do a bit of soul searching to try and figure out what’s missing… is it actually about the money? and will a raise make you feel better about your role? Are you more worried about your next step, perhaps you’re thinking this is as good as it will get? Would having a degree make you feel less “imposter” like? It really comes down to what the missing piece is.
RickShameless
Good Citizen
0
Accounte Executive
You're asking the right questions for me, Dwight. Thank you for the response. Soul searching is the hardest part. I hope I get my answer. 
dwightyouignorantsale
Politicker
0
Account Executive
you’ll figure it out sooner or later; I’m confident in that. Best of luck to ya!
Kry
Good Citizen
1
Lead Alliance Manager
The best advice I can offer is to expand your circle - set career and personal goals for yourself 2 years, 5 years, and 10 years out. Whether it is getting to a VP title in 10 years, or having a serious relationship in 5 years. Set goals and visualize them. 

Additionally, one thing I have always found helpful is not only seeking mentorship from individuals who have done it before me but I also seek to mentor folks that are coming up after me. It opens your eyes to a lot of different perspectives.

To start write down your goals that you want to achieve and work backwards from their - wants you have goals you can establish a plan to achieve them and put your goals in motion to see progress. 

Happy to hear any other approaches to this challenge!
letmeofferyouthis
Opinionated
1
SDR Trainee at Ramped Careers
Buy yourself some property. Go travel. Just set yourself a new goal man.
goose
Politicker
0
Sales Executive
Can't finish college, can't finish car sales, can't finish AE role...  I sense a trend.  
MinisterOfChaos
Politicker
0
Commercial Account Executive
First, take a deep fucking breath. You are 24 years old. Barring a catastrophe or horrific accident, you have plenty of life left to live. Embrace that.

If you are unhappy in your current position, find something new. 

If you are happy, but you're just looking for something extra, find a hobby, start a side hustle, travel (I know it's rough right now), etc. If your company has offices globally, figure out if that's an option for you. Nothing like learning how to sell in a different culture.

If you are seriously questioning whether or not Sales is right for you, talk to team members in other departments at your current company. Ask them about their day-to-day. If something sparks your interest, inquire about making that type of change.

At times, as many others have said, we all get in a rut. Leverage your support system to help you re-ignite a passion or reset expectations and think of a different goal for yourself.

In regard to the feeling of imposter syndrome, that never goes away. You may reach a point in your Sales career (or any other career you choose to pursue) when you don't necessarily feel that way, but it will rear its ugly head in other aspects of your life; I wake up daily as a father facing the demon of imposter syndrome. You need to learn to live with that and push through.

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