How to Up-Skill for a Promotion Even at a Dead End Job with No Opportunities

The moment you discover you’ve been toiling away in a dead-end job is a sobering one. I remember the instant I realized that I was going to be stuck at the same level for longer than forever.

I remember it was annual review time. My favorite time of the year (nope, not kidding.) I’d been with the company almost three years. I’d put in excellent work: pulled the team morale out of the gutter, helped sales climb back up to the five million mark, hosted c-suites from the home office, and piloted our outreach program.

It was all needed groundwork for something bigger and I was ready for it. I was buzzing with anticipation during the meeting as I and my boss’s boss talked turkey.

Then came my favorite question: Ok, Rowan. How can I support you this year?

This was the moment I was waiting for. I wanted a stretch project to prepare me for something beyond my current job title. So I launched into a marketing idea I developed to help our brand awareness at the field level. But something strange happened. The longer I spoke, the more frustrated I could see he was becoming. When I’d wrapped up, he shifted in his chair and said something that altered my professional trajectory.

*heavy sigh* "Rowan, that’s not your job. Focus on your own job description. I need you to stay in your lane. And stop asking about anything else."

A bucket of cold water got dumped over my head. I tried to mask my disappointment as I smiled and shook his hand, ending that meeting and closing the chapter on my future at the company. I had held the belief that that company desired to promote from within. I thought they valued developing talent and innovation. But even if that was true, I had a gatekeeper. I wasn’t getting any opportunities from this guy to help me move forward in my career.

So I had to think of something else. I had to get creative, think outside the corporate ladder structure. Thankfully, I learned three critical lessons that day.

1. You have to take your development into your own hands.

I’ve worked for several retail brands and although intentions may be pure, the chances of truly developing and promoting field talent is tiny. Brands with little structure, lots of structure, well meaning district managers, great team members… None of it actually translated into a promotion. I stayed at the relatively the same level for 8 years.

What I wish I would have done earlier in my career is take initiative. Do the thing. Write my own freakin’ permission slip.

I started taking on side projects outside of my J.O.B that were in line with the next step for me. I was done waiting for the stars of I’ve Proven Myself and There is an Opening to align.

If you also feel like you’ve put in great effort in your position, you produce results, and keep the ship sailing smoothly… but you can’t seem to snag that promotion or a step into a better job, then it might be time to create your own luck.

You can either make an impact where you are: institute some change that will get you some much-deserved recognition. Or you can start doing some work on the side to pad your portfolio. Whatever it is, the next step is not only to think outside the box, you need to break the box. Change the rules. Get creative.

2. Self-awareness is Key.

Knowing your strengths and opportunities gives you an edge. I wish I could say that all the leadership I’ve worked with have even-headed, wise, and malevolent. But I’d be lying. While I have worked with some truly inspiring individuals, there are those who are just there for a check. And it shows.

The biggest difference I see in people who are successful and stuck is their willingness to grow. If the desire to grow is there, they are the ones up-skilling, developing, asking transformative questions. In other words, when promotions or special projects come up, they are the ones top of mind.

Being self-aware of your strengths not only gives you a wheel-house to conquer, but it helps your team. Understanding how to apply your skill sets within the dynamics of your team is a hallmark of a highly efficient team.

So what does it really mean to understand yourself so well that you can open proverbial doors?

Self-awareness leads to self-appreciation and increased self-worth. Here are other benefits specific to your career:

  • You will be eloquent and persuasive with superiors.

  • You will become a magnetic storyteller with clients which leads me to higher sales.

  • You will be insightful on another level, so it helps you see a 30,000-foot view. (I use that perspective to create results while balancing all the daily minutia.)

At the beginning of the year, before COVID-19 shut the world down, I was weighing my options. I was deciding among three different companies. During conversations with the hiring managers, I gave unusual and memorable answers. My answers were at times weird. But they were uniquely me. And I was able to explain my role and how I could enhance each team.


You know that question they ask during an interview: give me three words to describe yourself? Most people say team player, creative, perfectionist (ick. My least fave answer), hard worker… Things like that.

Instead, I said: grout, jasmine candle, and Seabiscuit (yeah, the racehorse). The hiring manager burst out laughing, delighted, and completely caught off-guard by my answer. Before I could explain, she’d called others over to meet me.

From there I was able to explain exactly how I do my best work, what kind of team I am motivated and inspired by. Because of my total candor, she was able to see exactly how I would fit into the dynamic of her existing team.

I got the second interview.

Getting to Know You(rself)

If you’ve been feeling stuck on a hamster wheel, feel like you’re in a dead-end job, and know you have so much more to offer, then you can make a change too.

You have two choices right now.

Option one

What I see most people doing is realizing they would like things to be different and giving up. They believe odds will never swing in their favor, the status quo will always be… quo. Basically they believe their fate is in someone else’s hands. This is a vulnerable, diminishing, and sorry place to be.

Option Two

The other choice is to realize you have potential beyond your current circumstances and create an opportunity for yourself. If you have the desire, the inspiration, and the vision, then you can create that change. The difference between you and that other guy is that you are a doer. You see your fate is in your own hands. You’re about to break the box.

The change starts with some self-reflection. You need to take personal inventory, take credit, and stop qualifying. You’ve accomplished a lot to be where you are.

I like to break Taking Inventory down into three sections:

The Data (all the numbers and metrics you have directly impacted)

Soft Skills (these are the most important because they impact the results)

Energy (often forgotten, this category impacts the morale, cohesiveness, and trust of a team).

Once you’ve done a really good job of bragging on yourself, you have a fully stocked pantry with specialty ingredients you will use to create your banquet. (Yup, mama’s hungry writing this.)

These ingredients are the foundation of how you reinvent yourself, up-level your performance and impact, and develop a healthy self-appreciation.

For a The Complete 5 Step Guide to Being the Best Candidate, click the link.

3. Sometimes You Give More than You Recieve

When you’ve outgrown your workplace, it can feel like you’re just going through the motions. This is something you want to become aware of and put a stop to. I’ve been there more than once working in the field of corporate retail. It’s challenging, however when I change the perspective and get a little Camelot:

Ask not what my company can do for me, ask what I can do for my company