Generalist Career Profile #3: Natalie Hoop

Beyond Retail

Natalie’s story is a lesson in overcoming assumptions. 

We assume a college education is the only surefire way to achieve financial security and success. 

Natalie’s story challenges that. 

We assume retail is just one thing. We assume it’s something someone chooses because they don’t have any better options. We assume it’s a part-time back-up job until you find your real career.

But Natalie’s story shows us that retail can actually be an incredible container for learning and growth in your career, and that all of the skills acquired are extremely transferable and valuable across industries and roles. 

Her story is a testament to the non-linear career path. 

She knows what it’s like to backtrack, to reassess, to ask for help when she needs it. 

But she also knows what it’s like to prove her worth beyond the role she was hired for and leverage that to do work she cares about.

At its core, Natalie’s story teaches us the importance of making ourselves indispensable. Of finding gaps, taking on projects, and keeping business goals top of mind. 

Because no matter the title or industry, those traits are always valuable. And luckily, they’re challenges that generalists are especially well-equipped to take on. 

TLDR;

• Career: Retail (from part-time to District Manager), Educational Publishing, Startups

• Top Takeaway:

  • We don’t have to let the assumptions of others define our paths. We don’t have to embark on a degree because others say we should. We don’t have to only take certain roles because others believe we’re only capable of one thing. At the end of the day, it’s up to us to decide, explore, and discover the best path for us.

In a Nutshell: Natalie’s Career Path

As a kid, Natalie loved reading. 

You couldn't find me without a book in my hands.

That love of words (and probably a TV show or two) led Natalie to want to be a lawyer when she grew up. 

I knew what I wanted to do. I was dead set. I wanted to be a district attorney, and I wanted to help people who were harmed and then bring people to justice. That was my mission.

She chose a college with that ultimate career goal in mind. But a first-hand experience with how the justice system really worked had her questioning her legal ambitions. 

My roommate at the time was involved in a court case…I went with her to all of the hearings…and realized that the law is a lot of red tape. There's a lot of process that goes into it. 

What she thought was “justice,” most often didn’t really look or feel like justice. 

I'm sitting in these courtrooms and hearing these stories,...and in so many cases, the punishment didn't fit the crime or maybe they weren't guilty, but they took the plea deal because it was cheaper or less time. And so I realized that the justice system isn't what you think it is. It is much more people having to operate with their hands tied and that was not something I wanted to do.

In the meantime, she had started working retail part-time to make some extra cash. She ended up getting offered a full time role as Assistant Manager and decided to take the plunge. 

I was offered an Assistant Manager job, which to an 18 year old kid was more money than I had ever thought I could make…I decided to leave college and go into retail until I knew what I wanted to do. It didn’t make sense for me to pay for an education where I didn't know where I wanted to be.

The decision to leave school was like a gut punch to her parents.

Neither of my parents had gone to college. And so this was a really important thing that my siblings and I went to college and got a degree. It was drilled in my head from a very young age that that was the way to secure your future.

But Natalie slowly realized that college isn’t the right path for everyone. And having a full time job lined up - one where Natalie could afford to move into an apartment of her own - softened the blow when she broke the news to her family. 

I can do it. I'll have income coming in and I'm gonna do this until I figure out what I want to do. I think it allowed me to feel more in control.

As a budding generalist, working in retail turned out to be an incredible container for trying out and acquiring a ton of different skill sets. 

It was honestly the best education I could have gotten…When people think retail you think, oh, a cashier, but that’s not the case. You have all of this transferable knowledge because you do a little bit of everything so you can figure out, Oh, this is part of the job I do not like oh, this is where my skill set really shines.

Over her 20 years in retail - Natalie did a little bit of everything. Working her way up from Assistant Manager of her store all the way to District Manager, Natalie is living proof that retail can be an incredible engine of career growth (and not just the negative stereotypes that we associate with it).

You hear retail and you think customer service, you think somebody that is offering service to another human being, but that is not actually what retail is. Retail is being a generalist. If you are in any type of leadership from supervisor all the way up, you are not just in charge of one aspect, you are in charge of many aspects. 

First, you’re in charge of people management. 

As an assistant manager you are in charge of leading people. You are in charge of HR policies, documenting them, hiring, performance management, coaching, performance reviews.

Then, there’s inventory. 

You’re also in charge of inventory; making sure that you have the correct inventory, that you are ordering correctly, that the supply chain is on time. It’s working with a lot of internal and external vendors for product lines and trucking and logistics companies. 

Then, there’s budgeting. And back when Natalie started - those budgets were on good ole’ pencil and paper. 

You are in charge of making sure that your margins are correct….They gave you your historical figures from last year…and they gave you a goal. So they said at the end of this year, we want you to make this amount of profit. And you had the sheet and you were in charge of saying okay, based off of this I believe I'm going to do this amount of sales. I'm going to have this amount of labor. I'm going to do this amount of expenses. This is what my rent is going to be. And I had to write it all out and mathematically do it….So accounting, forecasting, capacity modeling, all of that was huge. 

And then, of course, marketing. 

How to merchandise, how to do impulse buying, how to specifically talk to people…how to upsell, how to product match.

And outbound sales.

You also have to proactively get sales. So event management, client services, business accounts, offsite events. 

Not only do you get exposure to how things are done in your store, you have the ability to move to other stores and see how things are done elsewhere. 

And so you can also see how other managers run their stores. Do they run it differently? What do you like about it? What do you don't like about it?

Beyond exposure to different roles and work styles, moving stores also meant exposure to different demographics, cultures and religions. 

So for instance, you could go into one of your stores, and it could be really Catholic and so maybe the books you carry or the holidays that you need to gear up for could be completely different than going to another store 10 miles down the road where they're Jewish and so you have to know the Jewish holidays and stock the right authors.

As you move up the ranks, you can find yourself planning and supporting construction and growth initiatives.

When you are doing store management or multi unit, then it's building new builds. It's working with corporate offices, communication. In a lot of cases, I had to go to Chamber of Commerce's or to go to the local municipality and get permits so my contractors could come in. 

But after 20 years, Natalie found herself feeling worn down and ready for a change. With a young son at home, the extensive travel was proving untenable, not to mention feeling the limitations of working within corporate bureaucracy. 

I didn't think I could make as big of an impact as I felt that I used to make. Corporations take a really long time to make changes at the higher level. At a store level, it's really easy to make a lot of changes and be impactful. But as a District Manager, you're kind of a bridge between your stores and corporate and you can't always get the changes that are needed on both sides to happen.

So she quit. It was the first time she had quit without another job lined up. Unsure what might be next, she looked toward roles in Corporate America, assuming that was the logical step coming out of retail. 

I was like I need to get my foot in the door. I will take any position in corporate. I just need to get in there. And that will allow me to get to my next level.

And it didn’t work. Even after going back and getting a bachelor's degree. 

I got this fancy degree that I knew I needed because that's what I was told in my head - my limiting belief. The only thing stopping me from getting into corporate was my degree. [Even with the degree], I went on a ton of interviews and I made it all almost to the final rounds. 

But there were no offers. 

After all the rejections from corporate, Natalie needed to take a step back and evaluate her options.

So I was like, What else do I like to do? Like let me rethink my path. So I ended up taking a huge pay cut for an entry level job at an educational publishing company. 

It was here that Natalie started to embrace her generalist skill set, realizing that they could be applied across a variety of businesses or anything she wanted to do. 

I was Jack of all trades. I came in for customer service, and then quickly did everything from working with the marketing team, creating campaigns, inside sales. They had me do inventory. I was managing huge inventory numbers between our company and state warehouses….And I realized my skills are vast and can be applied to anything I want to do.

She used this insight to pivot into the startup world, although she was still wary of employer’s assumptions about her retail experience. 

I still had that limiting belief and really was like, okay, the easiest way when people think retail, they think customer service, so I started looking for roles where I could manage customer service teams. I knew I had the skill set, I was confident in that skill set. And I felt it was very easy to explain the value and give specific numbers and metrics that I was able to achieve by coaching my teams. 

Her first job at a startup involved managing a bilingual customer service team. While she didn’t speak Spanish, she decided to download Duolingo and start trying to learn to make sure she could be the best manager possible. 

I can't ask [my team] to help our clients and then not be able to also help the clients. That is not a reasonable expectation. I'm never going to be as fluent as [my team], but I should be able to read a communication and be unable to understand what the customer is asking enough that I can help solve it.

Taking on new skills based on specific project needs was fast becoming a trend in Natalie’s career. Even in her current role as a Program Manager (a quintessential generalist job title), she assesses project needs and then seeks out the skills, resources, and experts needed to get the job done (along with lots of experimentation). 

My current role involves a lot of passive sales marketing. I have zero sales marketing experience. …So when I took the job, the CEO would ask a lot of questions and my response is okay, I'm gonna go research and get back to you. I will figure it out. 

She soon realized that her ‘figure it out’ attitude was an extremely valuable trait - not to mention something she enjoyed. 

That's half of the fun is figuring stuff out when you don't know how to do something, but you'll figure it out. So I was running these campaigns and figuring out which marketing and messaging works with no background. But the CEO was willing to take a chance on me because I said I was gonna figure it out. 

Natalie also discovered that working in the startup world means there’s a lot of you don’t know what you don’t know. She managed to make herself indispensable on a variety of teams by identifying knowledge and process gaps and spearheading projects to fill those gaps. 

A lot of projects come up by pointing out where there were gaps either in foundational operations or procedures that needed to get created and then handling it. 

While exciting, transitioning to startups wasn’t the easiest of moves. 

It was crazy learning that most startups don't make a profit…When you come into retail, the be all and end all is profit. If you are not profitable, they will shut down your store. You live and die by profit. So coming into startups was very hard. 

Fortunately, Natalie was able to leverage her retail background to bring a different perspective to the startup world and drive real value. 

I would look at where we could increase capacity and productivity, without aggregating the service and save labor. And so a lot of that is being able to go and either automate processes or working with product or engineering on friction points for the customer, that if we could just solve it that would release this amount of labor every week, and then doing calculations to show how much money it would save in the long run so they could make an informed decision around spending and potential ROI. 

Yet another example of the value of her “retail education.” 

The GeneraList: Generalist Thoughts & Trends 

When transitioning out of retail, Natalie came up against others that put her in a box. 

I had a lot of people, companies, jobs, that…really focused on this idea of No, no you only do retail, there's nothing else you can do.

But once she managed to make that leap, she came to understand that she had a generalist skillset. And that skillset was valuable. 

I've been in that job transition where I thought maybe this was impossible, and it wasn't going to happen. And then when I did it, I was able to realize what my skill sets were and that I was a generalist…And this is a common theme of people who want to transition or go into another role, and they don't think that they can, it's really a mindset issue. And so I don't want people to be stuck where they don't want to be. 

While it’s important to recognize your own skill set, it can be challenging to truly communicate the value of your skillset to potential employers - especially when they believe a specialist would be the best fit for a given role. 

Explaining your value in a job and getting that hiring manager to really rethink what they need is a huge challenge. 

Generalists are often industry agnostic, shapeshifting and diving into new industries and soaking up information like a sponge. But getting employers to recognize that can be a major challenge too. 

You know that there are a lot of companies that are excited about hiring generalists, but still believe that they need to have background in a specific industry. And honestly a true generalist does not need a background in the industry because they will go in and figure out the industry and learn, absorb it and be able to be productive no matter what the industry is. 

On top of that, being a generalist can come with serious financial tradeoffs. 

We're all programmed to believe that in order to make more money, or gain more impact or clout, you need an additional title. And generalists at the end of the day, don't care really about the title, but in a lot of cases salaries for roles with generalist titles are kept at a lower end. Maybe you cap out at 80,000, but if you've been a generalist for 20 years, like that's probably not the salary you're going to want anymore. 

While generalists may progress in their careers, generalist salaries often remain stagnant - leaving many generalists at a crossroads. 

There's not enough positions that are available that have the salary requirements that most generalists want as they get further along in their career, which makes a lot of generalists feel that they have to pigeon-hole themselves and pick one type of department.

Despite this, the term generalist is resonating with more and more people these days. Natalie says the proliferation of startups can explain why. 

There are so many more startups and there were 20 years ago, so more people find that they like to be a generalist if they have worked for a startup because you have more of an opportunity to try lots of things. 

The nature of today’s job market is another potential reason why the term generalist has been gaining traction. 

I think the other piece is this job market. I think it used to be very easy to submit your application and get 10 interviews and not have a problem and I think in this one, it is impossible to get any type of interview or job. I know so many people that I've been connecting with recently that have been in the market for a year and they're struggling and they may not even be a generalist but the market is not what it used to be. 

Because of this, more and more people are exploring how they can present themselves to future employers in a way that will land them an interview. 

And in a lot of cases, their concern is my experience is a jungle gym. It is not a linear path. It's very hard for me to show this to anyone and get a connection on the other end who's reading these resumes or applications. And so I think that's why I'm hearing the conversation more because people are trying to talk about these challenges. 

Despite the challenges generalists face in today’s job market, Natalie still staunchly believes in the value of a generalist career path. 

I'm starting to hear the term generalist a lot more. I'm starting to see that more people are connecting with it. I just hope this trend continues…I'm hoping this is the start of a change because I think there are a lot more people out there who want to be a generalist, but either don't think they can or don't see a career path for them. And if career paths start getting built out for generalists, I think it would be so beneficial for employees and employers both.

And believes that there are a variety of roles that can be a great fit for generalists.

Business operations, product, or program management. I know a lot of people don't think about it. But if you're a project person, if you can run a project in one type of industry, you can run it anywhere. And I think generalists do really well running projects because they take into consideration the impact across multiple departments, and both internal and external stakeholders.

But given the amorphous nature of job titles, Natalie says it’s extra important for generalists to read job descriptions in great detail. 

What I have really learned throughout my career is one title and one company is not the same as at another company. You really have to read the job descriptions and interview to find out what they expect from that role. I have unfortunately taken roles that I thought in the interview process I had vetted enough and then when I got there I realized it was not what was going to make me happy.

Natalie’s Advice For Navigating a (Generalist) Career

1. Make educational decisions that are right for you, not just ones that are dictated by our families and society.

I ended up going back to school later on. I paid my way and I did it…I did an online degree while working full time and raising a kid and I was like, You know what, I need to finish my bachelor's because it's going to help me from a knowledge perspective and a job perspective. And guess what? It did not.

All of my classes were things I had already learned in my career. I had real hands-on experience. Nothing was new. I learned zero in that degree program. And it was because I had people, bosses, mentors in my career who gave me that knowledge for free. 

I thought it was going to open all these doors, but I got 0 additional opportunities by having a bachelor's degree. Most people didn't even think to ask me if I had a degree even if it was not on my resume. It was never brought up in compensation. 

But I truly thought that is what was needed in order to get a higher level job because you hear all the statistics about people who did it and it helped them make more money. It did zero benefit for me except given me student loan debt. 

2. Narrow down your next desired career move.

The first thing you really want to do is gain clarity. If you are transitioning from point A to point B, you need to figure out where your point B is. I think in a lot of cases, generalists are so open that they'll take anything and it may not be the right fit or the right move. So really gaining clarity on where you want to go as your next move I think is huge. 

3. You can ask for more than what’s offered. 

In terms of whether you think you can get there, that's a mindset issue. And it's one that I work on every day, honestly. I hired a career coach to help me. I needed it. I needed to get my mindset, because I was stuck at a point where I thought I had to take what was offered instead of what is what I need. 

4. Don’t undervalue your skills.

When you're transitioning,... you think you have to take all those steps down or you have to backtrack in order to reprove yourself. You don't. Your skills are extremely valuable. There is a company out there that wants them. You just have to get clear on what you want to do.

5. Don’t wait around. If you know a role isn’t right, leave (if you can). Trust your gut. 

Context: Natalie had wanted to leave a job she didn’t feel was right, but was convinced to stay by her boss and coworker. 4 months later she got laid off anyway. 

I was just miserable. It did not serve them or me. And now when I got laid off I was crushed because again it was only like four months later. But you know looking back on it now I'm like, Oh, they so did me a favor and I can tell I was just miserable. And I should have just trusted my instinct. When I wanted to pull out I should have just pulled out and I should have not let anyone talk me out of it. 

What stood out most to you about Natalie’s story? What did you learn? I’d love for you to comment and let me know. :)