Three Things to Consider before Making a Career Move
In seeking inspiration for my next Recipe for Success, I did an Instagram AMA, one of you asked “I’m starting to think I need to make a job change, but I am afraid. What advice do you have on dealing with the fear of changing jobs?”
First and foremost, I love this question, because making a big career change is indeed a scary thing. Coming from someone who lived by the philosophy of using your 20s to figure out what you like and want to do, I’ve made my fair share of career changes. So in this article I am sharing a few things that have always been considerations for me when making these big moves, in hopes of inspiring you to have more confidence when evaluating a potential change in your career.
I love a three part essay, so I’ll give you three things to consider: the obvious, the less obvious, and the least obvious advice I’ve picked up along the way. My hope is that if you’re considering a job change, these ideas will help you maximize your personal happiness, your professional skills, and your personal wealth!
Okay, so let’s start with the obvious —
If you’re entertaining new job prospects, you are searching for something. What is that something? Is it more pay? A better boss? A new industry? More stability? More startup-y? What is it that you are chasing as part of the next experience for your career? Spend some time journaling into the reasons why you are considering a change and what the qualities are of the thing that would light you up the most.
I had a friend tell me once to make a list of the top 5 companies that I would literally DROP EVERYTHING to go to work for. If you’re struggling to get to the root of some of the questions above, perhaps this is a good place to start. Write the list of your top 5, and then write all the reasons for why you would drop everything to go to work for them.
If you’re going to change roles, what’s the job (or what are the types of jobs you’d entertain?), what’s the company (or what are the types of companies you’d entertain?), what are the pay and benefits (or what do you hope to make in your next role?), who’s the team? (or what are the qualities of the exec leadership team, your manager, and your peers that you would love to find in your next role?) Most importantly — how do these things compare to your currently situation?
As an example, when I was in my early mid-twenties working as a Product Manager, I came to the realization after about 2 years doing Product Management work (building software) that I was very unhappy in the work that I did day to day. In working with this coach, we assessed my skillset and looked at moments in my day when I achieved “Flow State.” One of the things we found was that for me, I always achieve flow state during “High Stakes Presentations” (think: a sales pitch, or pitching a new capability to add to our product roadmap to a senior executive stakeholder), in addition to this, we also came to the conclusion that some of my strongest skills were “Storytelling” and “Data Storytelling.” After sitting on some of this guidance, contemplating the decision to change careers, and what I would want out of a career change, I realized that: 1) I wanted to be at a company in the Consumer Industry, 2) I wanted to be in a customer-facing role, and 3) I wanted to be able to leverage my storytelling/data storytelling skills to help consumer brands win in the market. Shortly thereafter, I found a wonderful new home as a consultant for emerging consumer brands, helping them tell their story and data stories to retailers, like Target and Whole Foods, so they could win space on those coveted retail shelves. Roisin Branch, xCMO of Soul Cycle and current CMO at Blade, told us a similar story when we asked about her journey to leave the wellness industry for air mobility.
Next, we need to combine the obvious with the less obvious —
When I was early in my career, I thought more about what I didn’t like about the roles I was in, and let the “what I didn’t like” propel me to action. Didn’t like some poor decisions of my executive leadership team? Leave the company for a renowned leadership team. Didn’t like the day-to-day work of Product Management? Leave the company for a role that was customer-facing. Didn’t like working from home too early in my career? Leave the company for an “in office” company.
What I didn’t consider (and somehow managed to accumulate anyway), was what each move in my career could do for my skillset.
I started my career as an analyst for a data company, learning how to crunch numbers to help solve business problems, then I was promoted to a sales, marketing and customer retention role, where I learned the value of the GTM functions and how they worked together to grow company revenues, after that I spent time in Product Management, understanding how products went from little ideas to game-changing technology, thereafter, I found my way back into customer-facing work via consulting, channel sales, customer success and ultimately that led me right back to sales, marketing, and even starting my own company for a few years. I chased exactly two things: the ephemeral high of getting out of one situation where I didn’t like something, into another that seemed more promising than the last, and came with a bigger paycheck.
Hindsight is always 20/20, but I sometimes wish I’d had more foresight. Foresight to ask myself not just “can I make more money doing this?” but “Where am I headed?” Instead, it took me about a decade to realize one thing: I love sales and marketing, I love the consumer industry, and I love having the opportunity to make more money, the more money I help others make.
So here’s the less obvious thing about making a career change, instead of running away from what you don’t want, what if you were to run towards what you do want? If you’re going to leave your current post, what skills, key relationships, or experiences do you hope to gain or strengthen in your next move?
A few months ago, Lauren and I had Sarah Jahnke on the pod. We asked her about her decision to leave a prestigious career in fragrance at L’Oreal, for her startup in the home-care category, and she said “A mentor told me ‘Go where you’re going to learn more.’ And I decided to take the gig at Homecourt, where I would learn: [how to be a CEO, how to raise money, how to build a consumer brand from idea to in-market, how to lead a team of startup employees and so much more.]”
Again, if you’re evaluating a career change, you’re probably running from something or to something. Pause for a second and take inventory: Where have you been? Where would you like to head? What skills, key relationships, or experiences do you hope to acquire in your next move?
And finally, the least obvious — How can you maximize this opportunity?
A few years back, I was contemplating a career move that really tested me.
I was in a company that I truly loved. I loved the team, I loved the leadership, I loved the technology, I loved the customers, and I my role and pay. There was literally nothing wrong with this company whatsoever. I’d been there for a number of years, and I got a call from an old boss of mine about an opportunity to join her at a new company and build something from the ground up together. As enticing as this opportunity was, to be honest, I wasn’t sure that I would pursue it or not.
The place where I was at the time, was on the precipice of an acquisition by a much larger company and I thought I would stay with the business, see the acquisition through, and get to live that experience.
That said, when the opportunity presented itself to build something from the ground up, grow my people-leadership skillset, build my GTM chops (sales, channel sales, and marketing), and my executive chops (I was responsible for compiling and presenting to the board our monthly and quarterly performance), needless to say, it was very enticing.
It was about at this time I listened to a podcast (or read an article) about how when you move jobs to an external company, you’re essentially doing a “Personal IPO.” Here’s how it was explained:
When a company IPOs, investors don’t buy shares based on the current value of the company, they buy shares based on its future potential. The idea here is to think of the moment in time where you are deciding and negotiating your role, pay and other key benefits at a new company, as your Personal IPO… An opportunity for an investment in you, and your future potential to deliver value at said company.
You see, your current employer is paying you a salary based on your current performance, or perhaps even something closer to what your potential was when you started at the company, if you have been there a long time, it’s very possible that your open market value is much higher than your current wage. Now that’s not to say your current employer is taking advantage of you, in fact, that’s not the case at all, they are simply paying you based on the current value of your skills, in your position, at their company. It’s an equal exchange of value that the two of you have agreed to.
That said, when you start looking at external opportunities, a prospective employer’s offer to you is an investment and bet on your FUTURE POTENTIAL. They believe that you, above other candidates, can help them achieve their goals. And let me tell you what, as a hiring manager, hiring is damn hard. When you hone in on someone you really want, you really want them to say yes. And it’s in this moment — the moment where you have an offer on the table from someone who really wants you on their team, that you have power… the power to IPO.
So, back to my predicament — stay at the ‘being acquired company, or leave to build something from the ground up — I sat down with myself and did an honest evaluation: What would have to be true for me to make the move? What did I want the value of the stock of my Personal IPO to be?
The role itself had everything I was looking for, but there were a few things I’d need to have as guarantees to say “Yes” to the move: I would have to make no less than $X as a base salary. I would have to get an interesting number of shares in the company (as I would be forgoing potential future shares in my current role), and I would have to have a variable comp plan that should we be successful in achieving our goals as a team, I would be in a position to have the best financial year of my career.
Knowing this, I entered the negotiation with an abundance mindset: Yes, I was excited about the role and the opportunity, but it was going to be a “No” for me unless I was able to achieve my negotiation goals… my Personal IPO. And I was ready to do just that.
If you’re entering into a negotiation with a prospective employer, who is offering you an opportunity you really want, it is easy to say yes to the first thing that comes your way. Before you do, though, I’d like to encourage you to think about this: What’s the opportunity cost of pursuing this career move versus another one? Because by saying “Yes” to this, you’ll be saying “No” to a whole lot more. When you realize this, you realize that making this moment count is everything. So get your ducks in a row, make a list of what you want in your IPO and then come up with strategy to ask for it.
To wrap this up —
Every big career move I’ve made has been scary. In fact, I’ve often felt a good amount of Imposter Syndrome that I got each gig I did. That being said, I have found it’s easier to calm my inner voice of Fear by reminding her that I was searching for something and I found it in this new opportunity, that I was not running away from what I didn’t want, but towards something that I did want — something that would expand me, my skills, my network and my abilities, and finally, that I was adequately leveraging this moment to IPO, so that regardless of how things turned out in the long run, I would feel very much taken care of and supported in the near-to-medium term.
There’s no silver bullet for the fear that inevitably comes when you decide to step out of your comfort zone and do something new, but hopefully if you consider these three things, you’ll get what you want out of your next move, more often than not.
Good luck!
