Brutal Truth about Outside Sales in 2026 | SOS Ep. 382

Feeling stuck between underpaid and overworked after years in outside sales? We dig into the quiet mistakes that stall careers—abandoning your network once you land a role, clinging to low-yield activity, and trusting trophies to speak for you—and lay out a practical path to get your leverage back. The big shift is treating your career like an operating system you can design, test, and scale.

We start with the hard truth about timing and control: waiting until you’re unhappy or unemployed compresses options and pushes you into roles that don’t fit. With layoffs and market volatility, the only hedge is deliberate preparation. You’ll hear how top performers run concurrent plans—career, money, networking, and sales execution—so they can choose opportunities instead of chasing them. We also unpack why “President’s Club” rarely translates on its own and how to reposition your story around business acumen, territory turnarounds, and repeatable processes that win in resource-constrained environments.

Then we get tactical. You’ll get a simple pipeline assignment to cut 20% of dead deals and reinvest that time in higher-value targets using a P3 lens: past, present, potential. We share practical ways to grow a real network on LinkedIn—thoughtful outreach, insight posts, and case-style updates—so you’re visible before you need visibility. We close by reframing your professional identity as a sales operator who adapts fast to changing buyer behavior, including the new realities AI is creating in how customers learn and decide.

Want clarity on where you stand right now? Grab the free Sales Operator Diagnostic from the link in our bio, subscribe for more no-fluff career strategy, and leave a quick review to tell us which upgrade you’ll start this week.

Transcript

Why Mid-Career Reps Get Stuck

SPEAKER_00 0:00

The Surviving Outside Sales Podcast is hosted by Michael Kelly and presented by SalesDocus. Whether you're dominant, dominating, or getting out. Surviving Outside Sales.

The Hidden Cost Of Ignoring Networking

Market Reality Checks And Layoffs

Take Control With An Intentional Plan

Avoiding Arbitrary Deadlines

Build And Test Your Career System

Ageism And Strategic Career Timing

SPEAKER_01 0:16

Now, if you've been grinding six to ten years in outside sales and you still feel underpaid, underleveled, and overworked, I have great news. This episode is for you. Today I'm going to show you exactly why you're stuck in the three operator upgrades that can fix that. Now, if you're not between six and ten years in outside sales, you're still going to want to hear this because you're either one of two things. You're either before the six or 10 years and you need to know this stuff when you hit the six to 10 years, or you're over 10 years and you really got to hear this. So we're going to talk about your career progression. All right. And how you are in control of your career. You may not know it. I'm Michael Kelly. Thank you so much for listening. This is the Surviving Outside Sales podcast. Um, today we're going to talk about the common mistake that I see when I talk to my clients, when I talk to sales professionals. And that is not viewing what you're doing right now as a piece of a larger puzzle. A lot of sales professionals, they're just trying to find a job that pays well. That's all they're concerned with. And the moment they get their job, they post it on LinkedIn and they disappear. They don't continue doing the fundamentals needed to be a professional. Here's the problem, okay? There's a hidden cost to that. You're not building a network. You're not, that's your rainy day fund, folks. Your network, like LinkedIn, what have you, that is your rainy day fund. Okay. You have to keep building that. That is what is going to sustain you whenever you lose a job. I was working with a client and I got sent down a rabbit hole this week with LinkedIn. And I started looking at, and I was connecting with a bunch of people, and I was looking at a bunch of their LinkedIn pages. And I was I was shocked. I was absolutely shocked. And I was stunned. Because think about all of the advantages we have right now in this outside sales world, in the professional world. We've never been more, we've never been able to connect with people easier, faster, in more ways, more platforms. And yet on LinkedIn, there were some, there were some sales professionals with less than 300 connections. There are some that had less than 100, and you are in sales. That is scary. That is absolutely scary, and that's terrifying. And here's the problem, okay? Your network is not something that you can turn on at the drop of a hat. Okay. You have to constantly be building it over and over and over again, rinse and repeat. Okay. So you just believe, and it's a false belief, that oh, I'll just I'll apply and I've got a great resume and I know how to interview and all of that stuff. Well, I'm here to tell you as well, there are hundreds of other people in your market who are saying the exact same thing, but about 95 of them, oh that's a little high. Maybe about 85 of them have a bigger network than you. I heard a stat the other day that absolutely blew my mind. And it is that 74% of people on LinkedIn have less than a thousand connections. I could not believe that. No, I couldn't verify it. This did not come from somebody from LinkedIn, but it was one of the big um, it was one of the big influencers of like 50,000 followers or 25,000 followers, whatever. Said that. And I I didn't believe it at first. I couldn't believe it. That just doesn't seem real. It doesn't seem real to me. And I started doing some digging, and it is true. People do not have a network on LinkedIn. So the mistake I see is that people don't care about their career until they're unemployed or they're not happy. And that is the that is obviously the time that they take action. But unfortunately, a lot of the people that reach out to me, they're unemployed. And so what's happening is you are you're you're you're rolling down that hill or you're running down a hill, trying to keep your legs moving as fast as possible so you don't fall down. So what happens is you just take positions to take positions. And I spoke to somebody six weeks ago, so just after the new year, that decided to take a position. Um, I recommended against the position, not recommended, that's maybe to be too strong of a term, but I did not recommend that this person take the role because it wasn't a direct fit. And it wasn't in the direction that they wanted to go. Sometimes you can take a role in a different industry if you are ready for a change. That's totally fine. I've kicked the tires on some things in the past where I'm like, you know what? I don't really want to change industries, but if I did, it would be for this role. I've kicked tires. I it wasn't at a time where I just applied to every job on the board, but I've done that before. But this isn't what this was. This was just, I have to do this because I don't want to dip into my savings. There was this arbitrary line that was there. And I think that a lot of us create these arbitrary lines, these arbitrary deadlines that have absolutely nothing to do with um reality. Because in when you try when you shorten down this time period right now, where you have uncertainty of your job, you're unemployed, or you're in the wrong role, it's temporary. It is temporary. Over the years, you'll you'll stress out about a month, you'll stress out about three months. But think about your career. Your career will be 25, 30, 35 years long. What is three months? Now, if you're having to do this every other year for three months, yes, that's a problem. But the mistake that I see is not investing enough time, energy, and money into building a repeatable plan and a system for knowing if you're in the right role, getting out of the role if you're not in the right role, and finding the role of your dreams. Okay. And when I advise clients, this is the exact same things that I should have done when I was younger. I'm learning through mistakes that I make. I stayed a company's, I stayed at a couple roles way too long because I was quote unquote loyal. And then I realized what loyalty really got you in this world, which is nothing. There is no such thing as loyalty. There really isn't from a company standpoint. There was a there was a big company that laid off uh 600 sales reps so far this year. 600. And there's another company that laid off about 150 to 200. They had to clear their books and restructure. The executives kept their jobs. It was the entire sales team, regional directors down, lost their jobs. So they're just as loyal, they're as loyal as the next paycheck. So what are you gonna do to control your career? You have to plan it out. You have to be intentional. You can't just say, well, I'll get to it later. I'll only do it if and when I'm unemployed. Nope, it's too late. Because what happens is you don't get a chance to, you don't get a chance to take control, so you don't get a chance to dictate terms. You can only, I mean, if you're unemployed, you can only find a job that happens to be available within the time period you're looking. But if you have your eyes open, if you have a plan of what you want to do and what you want to achieve, and you start looking, or you start putting the, you start building your network, you start putting feelers out before it's time to exit, that is when you're gonna make the right decision. Because you're gonna, just like everything else, just like in the sales world, you're gonna build the avatar, you're gonna build the plan, you're gonna put in the actions, and then let the chips fall where they may. You don't have to take it. You're not applying for roles. You're just testing the market. You're you're putting feelers out, but you're building a network, you're letting people know how talented you are, what you have to offer the market. And in sales, it's about no like and trust. That'll never change. And it's the exact same thing finding a role. It's the exact same thing when you're trying to get your career. So the mistake is I'll just wait. It's not a priority right now. I don't need to do it. And the hidden cost is you're losing, you're losing that ideal career track that people have. Man, there's some, I look at some resumes and I meet some people that have ideal career tracks. I have not had, I did not have an ideal career track. And I'm telling you right now, okay? I was part of a lot of companies being sold, sales divisions being liquidated. The writings were on the wall, but when I was younger, I didn't do anything about it. I said, Well, that's not my problem. I don't need to worry about that. I just need my only thing is I just need to go out there and I need to do my job. That didn't work. I'm advising against what I did when I was younger. I learned by my mistakes. And if you believe that it's not important to you, trust me, I'm telling you, you have to be prepared. You have to have a plan. It's not a matter of when, or I'm sorry, it's not a matter of if, it's a matter of when you're gonna have to execute that plan. So, what average reps do is they just wait. They wait. They don't have a rainy day fund, they don't prepare, they don't build a network when they don't need it. They wait until they need it to try to build it, and it's too late. What the top five percent do is they constantly they build a networking plan, they built a career plan, they built a money plan, they built a sales plan, and they execute all of them concurrently. They're always tweaking, always testing those plans. They run them concurrently. That is what the top 5% do. And that is why I'm hoping every single person who's listening right now, and everybody who goes through Sales Builder Academy, that they get an opportunity to become the 5%. Because what you don't want to be is you don't want to be, you know, my dad before he passed, uh, he said, do not carry a bag into your 50s because there's ageism out there. So if you're listening out there and you're over the age of 40, you're getting close to the no hire zone. That's it's not to say you can't get a job. People over 50 get hired. It's just a lot harder. It's a lot harder. There is ageism in the sales world. And it's one of the things where, you know, people who have lots of experience have lots of experience that they want to share. They have lots of ideas about how things should be run. And that's not usually what a lot of companies want. They want people to just follow the playbook, don't, don't make waves, you know, don't don't give your opinion, things like that. So there's a three-part, there's a three-part idea that I'd like you to think about. Okay. And it's kind of the breakdown. Um, the first thing is the mindset change. All right. That's kind of the that's kind of pillar number one. All right. You have to have a new mindset, a new shift. This has to happen. Your beliefs have to change. And one of the beliefs, if you don't think this right now, this has to change. You say to yourself right now, as you're listening, in the car or wherever you are, I will not wait until it's too late.

unknown 13:31

Okay.

Three Upgrades: Mindset, Skill, Positioning

Why Trophies Don’t Translate

SPEAKER_01 13:32

I want you to say that to yourself. I will not wait until it's too late. If you wait to build your career plan, it's too late. You can't do it. You can't just float through. All right. Second is your skill upgrade. So the first one's your mindset, second one's your skill. Okay. So, what specific behaviors or systems must change? You're going to have to spend a little bit of your free time on LinkedIn. You're going to have to spend your free time learning new skills, new sales skills, new scales abilities, what is out there. You're going to have to take away some of your quote-unquote work-life balance. You're going to have to invest time, money, and attention to develop these skills and to change these behaviors. You can't just go out and do what you've done, you've done all along. I've had to do that. It's been painful. I've had to almost completely change in the last six to eight weeks what I thought I should do, I should be doing, what I was doing, the plans that I had, the frequency. I had to change it. It wasn't working. The market's different. Things evolve, things change, habits change, buyers' habits change. You're affected by what everyone else in the market is doing. It's not just you. You're not in a bubble. And the third is positioning upgrade. That's the third pillar, positioning upgrade. Okay. You have to market yourself differently. You can't just say, well, I'm, and I see this on LinkedIn all the time, oh, I'm six-time presidents club winner. I'm eight-time presidents club winner. I should get interviews. I can tell you that that might get your foot in the door, but nobody cares. Just because you there's enough examples of people who are president's club winners failing at companies, not doing well, that hiring managers, HR directors, district managers, that might get your foot in the door, but that doesn't impress them. That's not what you can just say. Well, I was this. What's your business acumen? How can you make how can you make the life of the people that are hiring you, how can you make their lives easier? How can you perform the task with the resources that you have? I've I've shared stories before about people who have left my the company that I work for before me. I've taken over their territory and it was an absolute train wreck and a dumpster fire. And they got they got fired because they couldn't perform, and they go to the next company and they make president's club. Because the companies I work for had very little budget, had zero name recognition, and had big, massive territories that they had to manage. So they couldn't handle that role. So each role is gonna come with its own challenges. So you have to work on your positioning. It's okay if you've won awards. Everybody's won awards. I've won like 40 some awards in my sales career. Nobody cares. Nobody. It's a what have you done for me lately type of economy. So it does not matter. How are you gonna translate that? How will you translate those quote-unquote awards, presidents' clubs? How will you translate those into this current role? That is your positioning. It's not just, oh, well, I've won presidents' clubs. I don't need any help. Well, if that were the case, why aren't people beating down your door for opportunities? There was a guy that I talked to about two weeks ago, and he was curious about sales coaching, et cetera. And I said, Why, why wouldn't you do this? I asked questions like, Why would you do this? I said, Why wouldn't you do this? He said, Well, I don't really need, I don't really need coaching. I mean, I've won presidents club eight times. I'm good. I'm good there. And I said, Okay, good there was let me ask you a question. Um, I see I'm just looking at your LinkedIn profile. Have you won President's Club at multiple companies? He's like, Well, no, it was all at one company. And I said, Oh, okay, how long are you at that company? I was there 12 years. Oh, okay. So I said, not to not to you know split hairs, but if I was interviewing you, I would ask the question, um, why didn't you win presidents club at every company you work for? What was different about that role that you won presidents club? I said, Do you know that answer? And he didn't know the answer. He got a little offended by it, but I'm like, hey, look, I'm not here to make friends, okay? I'm here to tell you the truth. I'm here to tell you my observations and prepare you. And I feel like that's what I was doing. And the guy chose not to, the guy chose not to get coaching with me, but that's fine. I don't know if it would have been a good working relationship anyway. But my role is to get people prepared for whatever it is sales call, interview. I'm gonna ask the tough questions because if if you're sitting across from somebody who has the perfect job for you and you can't get those answers, then I have failed as an advisor. I failed as a coach. So the three things again, mindset, skill, and positioning. You have to upgrade. 2026, you should be focusing on the upgrade. Those are three things that you should be focusing on mindset, skill, and positioning. So I want to do this, okay? I want you to do a little homework, all right? So I'm changing up things at the Surviving Outside Sales podcast. I'm I'm adapting to the times. Okay, no more is it just me being a talking head sharing stories from the field. All right. I'm gonna give you homework. And you can do this or you can't. It's just totally up to you, all right? Um this week, I want you to audit your pipeline. All right. The current deals that you have current you have right now, I want you to audit your pipeline, and I want you to remove 20% of the dead weight. And I don't care if it's recurring revenue. Um, I know in the pharmaceutical and the medical sales world, the disposable world, a lot of people like to go get quote unquote fake uh sales calls. They like to pad their stats and they go to accounts that are really low buyers. You're not gonna change their behaviors, you're not gonna change anything. You've given it the best shot, and their capacity is very low. On a scale of, you know, one to ten, they'd be fours, five, or sixes. You know, you need the business, okay? Those kind of keep the lights on. The small account, all the small accounts, the hundreds of small accounts, keep the lights on. But you should not be spending a ton of time on them if there's no hope for them to increase their numbers, okay? Remove them immediately. Not immediately, but you know what I mean? Like just don't make them a focus. I want you to all your pipeline, okay? And I want you to replace them with higher valued targets.

unknown 20:53

Okay.

Homework: Audit Pipeline And Refocus

Become A Sales Operator

SPEAKER_01 20:54

And I want you to focus on the higher valued targets. I want you to do whatever you got to do to focus on them. Get to know their business, get to know their needs, get to know their customer mix, their client base. What makes them tick? Who makes the decisions? Do the PPF. I'm sorry, the the the 3P. I'm sorry, the P3 sales method. Sorry, I've changed the name so many times. Uh the P3 sales method, uh trademark pending. Uh the 3P sales method, past, present, potential state. Dig deep into your top accounts. Don't dabble with these people just to make it look good on paper and activity. It's time for productivity. And I want you to do that because it's also uncomfortable. And I think more than ever, I think the one thing that I can do, the one thing that I tell my my coaching clients, but I don't really tell it to the podcast audience, is I I give them the straight, I give them the straight dope. I give it straight to them. No sugar coating. You're gonna rise and fall to your level of preparedness, you're gonna rise and fall to your level of effort, you're gonna rise and fall to your level of adaptability. So you've got to be comfortable with the uncomfortable. You've got to get out of your comfort zone. With that said, you can you got your homework, you got your mindset shift. So if this hits you, if this hits you like a ton of bricks and you're like, oh man, Mike, you're so right. Here's your next move, okay? If you want to know exactly where you're stuck in. Your sales career. I want you to download. It's a free download. I want you to download the sales operator diagnostic. Okay. There's a link in the bio. Go down to the bio, click on that link, it'll show you what tier you are operating at. You'd be surprised where you think you're going to be and where you actually fall. And this diagnostic tool is there to help you. It's there to help you analyze where you are right now as a sales operator. All right. Going back to the beginning of sales, surviving outside sales, I thought of myself as a sales builder, sales architect. All right. I didn't grow my territories because I was the smoothest, or because I did the finger guns, or, you know, I had the biggest budget so I could take doctors out and accounts out to eat. No, I did it because I created a processes and systems. I used frameworks within my business. I trialed, erred, built, scaled, rinse and repeat. And that's what I think that I that's the thing that can help most sales professionals out there right now. How are you as a sales operator? Not as a task completely, not as an activity warrior, but as a sales operator. The sales operator diagnostic is going to be the key to understanding yourself. And that's the first step and the big pivot that should take place in 2026. I really do appreciate every single person who is who's been listening. I had a little bit of a hiatus over the last probably two months. I've been in the lab, I've been in the sales lab. I mean, I have a new podcast set up. I know you can't see it right now. I have a new podcast set up, just a little, little different than what I had previously. I've been spending late nights, late, late nights, over and over and over, every single night. I've been working seven days a week, doing late nights because everything has changed. I'm not being hyperbolic. Everything has changed. Expectation levels have changed. I mean, I've always said that every quarter is different, but the way people buy and the way that consumers take information in has drastically altered because of AI in the last six weeks. And that's going to be the next episode you're going to see that. AI has killed outside sales, and I'm going to talk about it. Reminder click on the link to do the sales operator diagnostic. And uh thanks for listening. This is another episode of Surviving Outside Sales. Till next time. Cheers.