• Maya Grossman

5 Pieces of Career Advice That Will Completely Transform How You Think About Work

Do you ever feel like you don’t know anything? Like you are completely clueless while the rest of the world has it all figured out?


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I know the feeling.


I was lucky to have mentors in my life that taught me a few great lessons, but it still took almost 15 years to figure out some of the fundamentals. I want to help you get a head start, so in the next few emails, I’ll share the 5 pieces of career advice I wish I had when I was getting started, and hopefully save you some time.


I’ll also share a few ideas on how to start implementing the advice, so you can take action immediately.


Let’s get started.


Advice #1: You are not your job


For the longest time, I thought my value was derived from what I do at work and the title I was holding. My entire life revolved around work, and so did my self-esteem. If something went wrong at work, my confidence would hit the floor. I had to get a title, a promotion, or the recognition that came with being a high performer to feel good about myself. I let my work take over every aspect of my life, set my priorities, and drive my decisions.


That wasn’t good.


In theory, being dedicated to your job can be rewarding, but when you tie your identity to something as fragile as a job or a title, it’s a recipe for disaster. The first time I was out of a job I felt useless and unworthy and I couldn’t bring myself to believe I’m a successful professional, even though I had the track record to prove it.


It was a cold fall day when I finally had a breakthrough. My husband and I took the day off to relax and just walk around the old city streets, eat local food, and disconnect from the daily pressures. We were sitting on a bench munching chocolate chip cookies while having a philosophical discussion. My husband asked me how I define success, and I was finding it hard to come up with a good answer.


My initial response was “get a senior title and the salary that comes with it”. It was the “obvious” answer, or so I thought…


My husband smiled. “You know that’s not the only way to define success, right”? He asked. I didn’t. I never really thought about it up until that moment.

I had to buy myself some time to think so I asked him: “how do you define success?”

My husband thought about it for a minute and answered “to have the financial, mental, and physical freedom to do whatever I want to do while making a difference”.

(Damn that was a good answer).


I am probably miss-quoting him, but if you knew my husband you would know this is the kind of thing he would say.


Here is the thing, my husband is an entrepreneur. He built two profitable businesses and he is now working on his third startup. He could have defined success in profits, he could have talked about building a public company or being acquired by Facebook/Google/Microsoft (just choose your favorite) but he didn’t. Unlike me, he wasn’t optimizing for a title or a salary, he defined success as a state of mind.



(This is a real photo from that day)


Instead of focusing on a fleeting moment (trust me, the excitement of a new title wears off quickly), he thought of success as a state of being.


His answer got me thinking. Am I focusing on the wrong things? This conversation stayed with me for a long time and really forced me to think long and hard about my priorities and what success means to me.

I can’t tell you I immediately decided to focus on making an impact (which is how I define success today), but that conversation started the process.


I spent a decade thinking who I am is what I do, and it didn’t exactly make me happy. I needed a kick in the butt to start asking myself the right questions and finally come to the conclusion: I’m more than my job. Hopefully, this email will be your wake-up call.


Here is the bottom line: your value does not depend on what you do, the title you hold, or how much money you make. Your value comes from who you are, what you believe in, and the choices you make, not your profession. You can be unemployed, you may screw up an interview or move back in with your parents and you would still be an awesome, confident, valuable person.


I know, it’s easier said than done. I’ve been there, remember?


Here are two practical ways to get over this feeling and adopt a new belief:


1. Tie your identity to something that is antifragile. Something that doesn’t change easily or is not affected by changes you can't control. Your job is fragile - you can have it one day, and not have it the next one. You don’t control your job, even if you own your own business, there are still external forces that can break you. On the other hand, knowledge, skills, values are all antifragile. Once you acquire them, they are part of you. Even if you lose your job or the economy tanks, your knowledge and your skills will remain the same.


Why am I telling you this? Because if you are able to tie your identity to something that is antifragile, it won’t be affected by change easily. You will be more resilient and more confident in your abilities.


For example, you can decide to define your identity around learning. You can choose to believe what separates you and makes you special is your ability to learn and grow. Believe that on a long enough timeline, you’ll out-learn anyone and achieve your goals. Alternatively, you can tie your identity to your desire to help others. You can be the teacher, the mentor, the leader and derive your value from your ability to make an impact on others.


Find an antifragile anchor and repeatedly tell yourself (and other people) that is who you are until you actually believe it.


2. Find something that gives you meaning, purpose, and energy outside of your job. Volunteer, create content, start a side business, mentor, coach, dance, run a marathon… find something that makes you feel really good about yourself that is not related to your job.


I spent the first 10 years of my career JUST working. Seriously, I barely even dated or had hobbies because work was the only “important” thing. I wish I started my passion project sooner because it really had a huge impact on me.


I dreamt about launching a podcast for years before actually doing it. That passion project gave me so much confidence in who I am, that for the first time in my life I didn't break down when I lost a career opportunity I really wanted. Don’t get me wrong, I was upset, but unlike previous years when my identity was completely tied to my work, this time I had another anchor that reminded me I was valuable.


To sum it up: you are not your job. Although it may seem like it sometimes, your value is not summed up with your work experience or your title. Tie your identity to something antifragile so it doesn’t break every time the job market changes.


Now that you know you are not your job, we can take it one step further and talk about success and what it means to you.

If you remember the story from my last email you know I used to believe there was only one way to define success. Successful people move up the corporate ladder and they get the title and compensation that comes with it. I know now that I was wrong, but it was the only definition I had for success.

We are constantly bombarded with images of what success is supposed to look like, even though we are looking at another person’s success. We keep playing the comparison game, and more often than not, we end up on the losing end. Success means different things to different people and you get to decide what qualifies as success in your life. Success is what you want it to be, whatever makes you happy and keeps you fulfilled, not what society deems as “worthy”.


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If you choose to define your success as career progression - great, just know it’s a choice you can make.

Advice #2: You can define what your success looks like

I had this little identity crisis a few years ago, I started to realize I was not my job and that meant I had to find a new way to define success to feel like my work and my life had a purpose.

I was so confused. I wasn’t sure who I was if I didn’t have my job and my title to represent me (think about it - most people present themselves as “I’m Maya, I’m the head of blah blah at this random corp”).

I decided it was time to ask myself a few hard questions:

What makes me feel fulfilled? Proud of myself?

What gives me energy and gets me through my days?

What do I look forward to in and outside of work?

If I could only be known for one thing, what would it be? What would be my legacy?

If I didn’t have to work a day in my life, what would I do?

These questions helped me notice things that were making me happy. I realized helping others realize their potential gave me energy and made me feel good. Speaking publicly was another thing that made me happy so I decided to do more of it. It wasn’t enough though, because I still wasn’t able to define what success could look like.

If I train and coach 100 people will that be enough? Do I need to become a renowned public speaker to call it a success? I was slipping back into the old habit of defining success as “more” or “best” and I didn’t like it.

I decided to try something else. I decided it was time I found my WHY. I wanted to understand why I was enjoying coaching others or speaking publicly. Why did it make me feel good? After asking myself these questions I started seeing a pattern. Helping others and speaking publicly were activities that allowed me to influence others, to help people learn and improve. My joy didn’t come from the activity itself, but from the result - making an impact. That meant success didn’t mean being the highest-paid speaker or the most senior leader at my organization. Success meant actually impacting people’s lives. If I can change one person’s life in a meaningful way, I will see myself as successful.


(Recording one of the first episodes of my podcast...can you tell I'm happy?)

This revelation had completely changed my life.

I no longer optimize for a title or a salary when I look for a job. I look for opportunities to have a big impact. I actively seek out speaking opportunities and run workshops to help young professionals design their career roadmap.

This realization is also what eventually drove me to write my book, invaluable. When I asked myself how could I grow my success as a coach, I realized writing a book would allow me to impact more people. I couldn’t scale myself, so I decided to share my knowledge.

To recap: don’t limit yourself by using someone else’s definition of success. Search deep within yourself and define what success means to you. It will make you happier and more fulfilled in your work and your life.

For the longest time, I was under the impression that more was always better. If I worked more hours if I crossed off more tasks and took on more responsibility I would win.

Once again, I was wrong.

There is a big difference between producing outputs (a.k.a doing more) and delivering outcomes. It’s the difference between checking boxes and making a real impact.


Advice #3: It’s more important to get the right things done than it is to get more things done!


Spending the majority of your time doing things that impact your job, your business, your career, and your life is much better than doing more of the things that don’t matter.




I remember being very skeptical when I started to realize this was the case. I was afraid doing less will hurt my reputation and my ability to succeed. I needed some guarantees so I ran an experiment.


I outlined all of my tasks for that week and ranked them by order of importance. Then, I completely eliminated the bottom 20%. Do you know what happened?

Absolutely nothing! No one noticed or cared. Those tasks were not impactful, which meant eliminating them didn’t make a difference. The good news was that I got time back to focus on the things that moved the needle for the company I worked for, allowing me to make a bigger impact through my work.


It’s very tempting to do more of the fluff because it’s easier to show “success”, you just need to do it. Doing the right things requires more effort, and can take longer to achieve, but those are the things that are going to get you into the employee hall of fame.


What do you think will benefit a company more?


1. Creating 10 pieces of content that don't really drive sign-ups

2. Hosting one highly curated event that drives 10X sign-ups


If you focus on getting more done, you’ll create a ton of content pieces, but they’ll just sit in your blog waiting for someone to find them. If you focus on the outcome - driving sign-ups - you’ll spend less time preparing just one event, but you'll get a better result. Fewer outputs, but a much better outcome.


How to make sure you focus on the right things?

1. Set up goals around outcomes

2. Measure what matters, not what is easy to measure

3. Constantly ask yourself: will doing this task move me towards my goal?


To recap: more is not always better. Focus on getting the right things done to make a real impact.


Let’s talk about a big misconception. Most people think their success at work is out of their control. We are brought up to believe we are supposed to play the game, wait for our turn, and hope that the opportunities we want will magically find their way into our lives.


Let me tell you a secret, hope is not a strategy.


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Advice #4: You can create your own opportunities


If you want to achieve anything in your career you need to create your own opportunities and drive your career forward.


I started my career in the travel industry. I never asked myself if that was what I wanted to do, I just woke up every day and went to work... for 7 years!

One day, I fell in love with marketing and realized I had to make a change. I had to take control over my career and come up with a plan that would give me an opportunity to land a job in marketing.


Here is how I got my first marketing job without "real" experience:


1. I figured out what it took to be a social media manager - I read every blog post, tweet, or piece of news about the topic to educate myself. I invested more than 50 hours over a few months.


2. I then reached out to my manager at the travel agency and offered to create social media pages for the agency in my spare time. I knew I needed hands-on experience so I created an opportunity to run social media within the travel agency.


3. After a few months, when I gained some confidence, I started applying for social media roles and got my first marketing job.


I waited 7 years to make a change that took 6 months of work and made me 100x happier. Don't do that.


You have the power to design your own career roadmap. You don’t need to wait for your manager, the company you work for, or anyone else to give you permission. It’s up to you to imagine the future, figure out what it takes to get from where you are now to where you want to go and do whatever it takes to get there.


Do you want to become a manager? Volunteer to mentor others. Do you want to get a promotion? Start doing your superior's job before you actually get it. Do you want to pivot into a new profession? Spend time with the relevant team inside your organization. Help them out in your spare time and learn the ropes.


Okay, so how do you go about creating your own opportunities?


You need to be an opportunity digger.


1. Proactively seek out opportunities. Set time on your calendar to work on this task.

2. Define your goals. Not all opportunities are created equal. What are you trying to achieve? What are you hoping to learn? Be very specific about your goal so you can come up with a relevant opportunity.

3. Always be in the know - keep yourself up to date with company and industry news, know your company and business inside out, and engage with other teams to get the bigger picture.

4. Build relationships. People will open doors for you.

5. Ask for opportunities - talk to your manager/colleagues and tell them what you want to do or achieve. They may be able to help.

(I share these and a few other ideas in more detail in my book).


Recap: you can create your own opportunities, you shouldn’t rely on hope to get you the job, raise, or promotion you want and deserve. Figure out what you want and what it takes to get there, and create your own opportunities.


I’m the most annoying person when it comes to coloring inside the lines. My dad was an army sergeant so I grew up following rules and obeying orders. I’m wired to do exactly as I’m told, but early in my career, I learned that’s not always the best strategy.

I’m all for following the rules, but sometimes, the rules are…well, stupid.

Especially in the workplace, some rules may be outdated, irrelevant, or simply illogical. They may stand in the way of innovation and growth, and in those cases, it is better to take action and ask for forgiveness, instead of asking for permission.

Advice #5: It’s better to ask for forgiveness than it is to ask for permission

I learned that from my manager at Microsoft. Our team was about to launch a new program and we wanted to share the news in the press. I had vast experience dealing with bloggers so I put together a press release and was about to send it to a few of my contacts, when I learned I was not allowed to do that.



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Apparently, there was an internal approval process we had to go through to get sign-off on our press release, and we had to work with the PR team to pitch the story to journalists. I was happy to do all of that until I learned it would take 2-3 months to get a spot on the PR team’s calendar.

I couldn’t wait that long, but I also didn’t want to get into trouble… so I came up with an idea that was not exactly against the rules, but wasn’t 100% kosher either. I rewrote the announcement as a thought leadership piece. Instead of making it all about the program, we shared valuable knowledge and ended with a short mention of the program as part of the educational piece. This was no longer a press release, but an op-ed, and I was allowed to pitch those myself (well technically no one told me I could do it, but there were no guidelines telling me I couldn’t).

This article became the first story in a series of articles that got a ton of exposure. It got so popular the PR team took notice and complimented us on the achievement… I mean… facepalm.

Now, a word of caution before you break any rules. Use common sense to decide when to cross the lines, and when to be compliant. I would consider breaking the rules when it impacts my ability to deliver results or interferes with my team’s ability to succeed. I probably won’t do anything that could jeopardize the company’s reputation or have a massive impact on the business. There are other ways to drive company-wide change, you shouldn’t do it by breaking the rules.

Also, remember breaking the rules doesn’t always go to plan. I got slapped on the wrist more than once and had to apologize after the fact. But If I’m being honest I have received more praise than criticism for consistently breaking the rules to get the results I needed for more than a decade. It’s one of the practices that fueled my success.

Unfortunately, when it comes to my own good, I’m still really bad at breaking the rules. I never book the more expensive hotel when I travel for business, and my expenses never pass the allotted budget, even though most employees do it all the time. Once an army brat, always an army brat.

I hope after reviewing these 5 pieces of career advice you feel more confident. It took me more than a decade to figure everything out, so hopefully, this advice will save you a few years.


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