Have A Focus Role, And Know It's Not Gonna Be Easy

Erin Lewber’s name comes up a lot in teacher transition spaces. She’s been on the scene longer than most, offering tips on LinkedIn, a free resume template, and well-reviewed coaching services since before the pandemic. In addition to coaching, she also leads a global sales team at Amazon (nbd). We were grateful to sit down with Erin and hear her thoughts on all things career change. Thank you, Erin!

How did you get into coaching?

I lost my job back in 2011. I worked in a family business and very quickly, I found myself going from this vision of, "I'm gonna inherit this someday" to, "What am I gonna do?" I had no idea how to tell somebody how my skills made sense for a job at their company.

I floundered a lot. I worked for Trader Joe's corporate for a little while, which was a wonderful company. But I just knew long-term, I didn't want to be in retail.

I moved into staffing kind of accidentally. Suddenly I found myself in a corporate setting, having never sent a calendar invite or sat in a meeting before. I just kept thinking, "Does somebody know that I have no idea what I'm doing here?"

But that was the start of me learning about hiring, job searches, and recruiting. I was working with candidates, reviewing resumes, talking to hiring managers, understanding job requisitions—it was really cool to learn. I stayed in that industry for about six years.

Right around that time, I started helping people with their resumes and job searches informally. Just like, "Oh, I'll help you out for 50 bucks." It was just fun because I knew what it felt like to be in a really tough situation and not know what to do.

Fast forward—I moved to Amazon in 2017, and I started posting on LinkedIn… I ended up connecting with some of the early leaders in the teacher transition space, like Stella Igna and Raven Wilson. We started having teacher talks and doing webinars, giving advice. At the same time, I got a life coaching certification.

Now, most of my business is word-of-mouth. I post daily on LinkedIn, and I work almost exclusively off referrals. I always joke that I just do this so I can make friends. I've stayed at the houses of former clients, and some of them have become my closest friends. 

It’s just been a really cool evolution and a fun project with a lot of purpose along the way. It’s a cool community. And I feel a little bit lucky, like I just happened into it at the right time. 

In teacher groups, I hear a lot of suspicion about career coaches. People are skeptical of their intentions and the value of their services. What you would say to a teacher who was on the fence and perhaps hesitant about hiring a coach?

I think you should absolutely be hesitant, because coaching is not regulated in any way, shape, or form. So anybody can turn around tomorrow and be like, “I’m a coach.” There are people on LinkedIn who are giving out advice who, not that long ago, were sending me messages about not knowing how to navigate their own situation.

So there is some concern around that because those people—I mean, they’re lovely people—but I just don’t think they necessarily have the experience and the multiple-perspective acumen to really advise somebody in a way that says, “Hey, I’ve been at the 10,000-foot view. I can tell you what works well overall.” Instead, they’re like, “I have my one situation where I did it one time, and this is how I did it, and I want you to go do it that way, too.”

Also, let’s be honest. Teachers are generally not paid all that well, right? So a lot of times, the cost [of coaching] is a huge component. Partnered with cost is this fear of, “If I spend this money, is this going to be worth it?”

There are things that are cheap. There are things that are on the other end of cheap. There are things that fall in the middle. And I think there’s a lot of self-worth or trust in self that gets tangled up in, “Am I willing to make an investment?”

What I see is, you have people who are not sure, so they deny themselves any support. They’re just gonna go alone. And then they just sort of bludgeon themselves into a wall for months, alone, when maybe they could have used a coach.

And then you have other people who think, “I have no idea what I’m doing.” And they’re so fearful they’re almost delusionally okay with parting with a big amount of money.

You hear those stories come out where somebody’s like, “Look, I got really bamboozled, and then I took the payment plan, and they didn’t say that there was going to be a charge on the payment plan, and so now I’m paying this amount of money.”

Pardon me for saying so, but those are really shitty human beings who do things like that.

But it’s real, and it’s out there. And so you start to hear these rumblings—everything that’s going on in your own head, plus, “Oh my God! It’s so much money. I don’t have this money, and I probably shouldn’t spend it. So, I’m just gonna try on my own.” And then you have the other version of somebody hiring someone and overcommitting financially and then having a horror story.

You can see where the paralysis almost comes in.

I don’t think everybody needs a coach. I think everybody can use a coach at some point in their life for something, whether it’s for a career transition or not. It’s very individual. 

I really like giving small amounts of information away for free to get somebody on the right track. I want you to do well. And I know that in the long run, that serves me because I treated you the right way—the way I would want to be treated.

But, you know, there are other times when it’s the perfect season for a coach because it’s a big, important move.

I’ve had a coach myself. I hired a more executive-focused coach in 2023 for more than $10,000. So not cheap. And I went into it thinking, “This is either gonna be the best or dumbest decision I ever make.” And it was the best, thank God!

But sometimes, your life is in that place where you’re like, “I know I need to do something, and this is the time where I’m going to put myself on the line and be on the hook.” And sometimes when someone is reluctant to work with a coach, there’s an opportunity to be curious about whether it’s really about the money—or if it’s about being afraid to commit in a big way because they don’t trust that they’re ready.

What’s a piece of advice that you feel doesn’t get said enough or gets overlooked? 

Okay, I’ll give you two.

One—It is not easy. It was never easy. It’s not going to be easy. Stop thinking it’s going to be easy. There’s nothing wrong if it’s hard. Stop quitting. There are so many educators who come up against friction and think it’s a signal to give up.

And it's not. People who've done it before you didn't just trip and fall into a new job. All they've done is maybe make it look easy, but it hasn't been easy. 

So that's the one thing—it's hard. And to think otherwise is really setting yourself up to be disappointed and frustrated before you've even started.

The other piece that I feel like I say over and over again is the idea of having the focus role, knowing what you want to go after next—it's step one. If you have not done step one, don't do any other steps. Don't hire someone to do your resume. Don't download my resume template and start working on it yourself. Don't make a LinkedIn profile. Don't be applying to things. 

Figure out what you want to do.

Because there's always that rule of—you have to translate what you've been doing to the language of wherever you're going next. And if you don't know—if you've been speaking English and you don't know if you're going to go to Spain or France or China—you don't know which language you need to practice and be ready to show up to speak. They're very different, and one doesn't work for the other.

It's interesting because I feel like I say it so much. I'm like, everyone must be sick of hearing me say this, but then I'll get 10 more DMs this week saying, "I'm just not sure why this isn't working, and I've been applying." 

And my first question is, "Can you tell me what you're applying to? Because I cannot tell from your resume. What are we trying to accomplish here?” 

And oftentimes, I get, "Well, this or this, or this or this," or "I was thinking about this."

So first, get that clarity around what you want to do next. And then, know whatever you pick, it's gonna be hard. It's not going to be a walk in the park. 

Are there any other myths you want to dispel about the transition process?

I think we've seen this go away a little bit, but it got really bad maybe a year or two ago, coming off the pandemic. There was a lot of hiring and [a lot of] remote jobs available, and you almost ended up with this attitude, "Well, everyone else did it, so here I am—give me my job, too."

I talked with a lot of hiring managers, and the word that kept coming out of their mouths was “entitlement.”

We had a lot of this in the EdTech space specifically. And then you see these posts where it's like, "EdTech is not nice to teachers. They don’t want to hire teachers." And it’s like, well, how did we get here? If that's true, let’s just try to be curious about how we ended up here. 

I think it was really sloppy presentation of candidacy. Showing up not ready, not understanding the job, and just saying, "Well, I can do anything." Well, yes, I'm sure you can, but you wouldn’t show up someplace unprepared and expect to be recognized as someone who’s prepared.

And we saw a lot of that. I got a lot of feedback from hiring managers about that, specifically with teachers. They’d say, "They just seem to think they’re next in line to get their job, and I’m just not seeing where they understand the discipline they’re trying to break into."

It seems to have chilled out a little bit. But just know, you have to come prepared and to do that, you have to have a focus role. And even then, it’s gonna be hard and take time. But it can be done.