2021 Reflections: Creating and Reflecting on Multiple Life and Career Transitions
My reflections on stepping away from corporate life, the journey to full-time soloprenuer, and what I've learned along the way
Note: this is a long post (5000+ words!)
TLDR: A few months ago I left my corporate job at Salesforce, moved to Los Angeles, and started my life as an independent worker/solopreneur. It’s been a great experience so far, and I wanted to share what I’ve been up to, what I have learned, and what’s ahead.
Backstory: Curiosity Filled Side Projects
I’ve always been very curious and enjoy doing things that make an impact, and always seemed to have something that I was working on. What you also may or may not know, as that I’ve always been a bit of a ringleader as well as have had hints of entrepreneurship in my blood.
In elementary school, I used to sell bags of chips to my friends at lunch. I got my first job when I was 12, and when I was sixteen, I started an internet business. Despite this, I always knew I wanted to work a corporate job, and spent the first 10 years out of college in the big corporate life. I enjoyed it thoroughly and learned so much working with amazingly talented and smart individuals.
While I enjoyed corporate life, I was always someone looking to find other things to work on that spurned my interests and curiosities, which has led to a number of different ventures, projects, roles and initiatives outside of my core day job.
Writing for Business Insider, Inc and other media publications
The most notable thing, which many of you probably know is through MBASchooled. I’ve talked about MBASchooled previously, but the short of it is, I started it because I was trying to solve a problem that I had when I was an MBA student, but decided to stay with it after I graduated from business school back in 2015. Over the years, it’s become a go-to source for MBA aspirants, students, and alum, and helped me launch my side-gig as a keynote speaker, career coach and trainer, primarily for MBA and undergraduate students.
In 2020, I published my book, MBA Insider: How to Make The Most of Your MBA Experience, and while the subsequent book and speaking tour got shut down due to COVID-19, I decided to start a podcast. Between the rush to go virtual and the halo effect of the podcast and book, I started getting a ton of requests for help, whether it was through 1:1 or large group work. At my heart, I’ve always been a coach, even stemming from my days when I coached youth basketball, and I loved the ability to help emerging talent build the skills to thrive in the workplace.
At the same time, while I had loved my time both at Deloitte and Salesforce, I was starting to wonder if the corporate life was still a good fit for me. Like many, I struggled during COVID-19, especially being in San Francisco living in an apartment by myself, and being isolated. I’ve always been a self-reflective person, and someone who was fairly self-aware, but I started to really think deeply and ask myself questions about my own life, such as
What is the meaning of work and life?
What does a good life look like?
What is important to me?
What do I want, and what am I willing to sacrifice in order to get what I want?
Furthermore after 14+ months of navigating a global pandemic, I began to struggle with exhaustion, managing stress and well-being, and taking care of myself. This, coupled with the energy and engagement I had working on many of the side projects that I had brought to life over the years created an interesting dichotomy in my days, where during the day, I was dialed in at work, and often exhausted by the time it was done. But then, at night, when I worked on all of the aspects of side projects outside of work, I began to develop a second wind, bursts of energy and creativity, and general vigor and excitement in what I was creating.
Over time, I began to pay attention and notice these nuances in these feelings and changes. And after awhile, things begin to compound, especially when you have time to yourself to reflect and think deeply.
The Corporate Game: Adults, Teenagers and Kids
In the middle of 2021, I started to better assess and reflect where I was and where I wanted to go with my career. While I had spent the entirety of my career working at large companies, The pandemic, my well-being and my thoughts around my future began to drive me towards a desire to make some changes.
Through alot of reflection spent in my apartment and on walks in my neighborhood in San Francisco, I found myself thinking back to all the times dating back to when I was a kid, where I got the chance to pursue my curiosity and interests untethered by time or others, to create and build things, to rally people together, and to share ideas and knowledge. I loved the thought of being able to get back to a place in life where I had more of this in my life.
Corporate life had given me many things that I am forever grateful for. But even before March 2020, I was beginning to wonder if this was the place I was meant to be. After spending time as a management consultant at Deloitte, and starting at Salesforce in 2017 as a product marketer, I was starting to realize I was at an interesting inflection point in my career: In my world of work, I liked to say that there were 3 types of people: kids, teenagers, and adults.
The kids were the order takers, the people who were just told what to do and then were asked to do that thing really well.
The teenagers were the people who knew a lot more and had experience (thus not kids) and often got to sit at the adult table during the holidays, but still weren’t quite in a position where they had authority or power.
And finally, there were the adults, the people who made the decisions, and aligned the kids and teenagers together to achieve the goals of the family. At that point in my career, I was a teenager, spending a lot of time with the adults (VPs, SVPs, other leaders,) I was starting to see more and more what life as an adult was like, and tried to think deeply about how that might look if I was going to be an adult. While there were aspects of this that appealed to me, there were others that gave me pause and concern.
When it comes to a job and a career, I like to say that everyone has a “give/get ratio,” a ratio of things that they get, and in return, what they have to give up in order to get those things. As a consultant, I got a chance to work on interesting projects and for Fortune 500 clients at a much earlier stage in my career. What I gave up was flexibility, sleeping in on Monday mornings to go to an airport and get on a plane, and some agency and control over my time. At 22-24 years old, the give/get ratio was okay to me for where I was in life and in my career.
But as I thought more about what “adult life” would be like in the corporate world, I began to wonder if the give/get ratio was going to work for me, at this stage in my life. I was fortunate to get a first-hand look at the work and personal lives of people a handful of levels and seniority above where I was. I also had the privilege of a network of peers and mentors who would share their insights and learnings from their own experiences, and in my part-time role as a career and leadership coach, I spent lots of time thinking deeply about the role of a leader or executive in a large organization, and started to realize that many of these people got objectively “a lot'“ (get) but also had to give up a ton (give) as well.
Ultimately, I decided that in order for me to get the give/get ratio that I wanted, it would be best for me to pursue a different path outside of corporate life, or at the very minimum, to take a break from it to see another path. To be sure, I did go through an exhaustive reflection process, and spent time looking at everything in between large corporate life (working for a 70,000+ company) and small businesses and anything in between. But ultimately, stepping away from the large company and corporate world made the most sense.
In the summer, I spoke to my team and our leaders and informed them that I was leaving to take time off and to eventually work on my own business/soloprenuer journey. They were incredibly supportive, and during that time of transition, I also made the decision to move to Los Angeles. I had loved my time in San Francisco, but I was also going through changes in my personal life. I had a newborn niece, my parents decided to temporarily relocate to Los Angeles to be near my family, and my girlfriend lived in LA. Once I knew I was leaving Salesforce, I decided to make the decision to move to LA as well. After 14 months of more or less staying relatively the same, I had made a huge transformation in my work and my life.
Many people who know me well would have said this was a long time coming, but I can assure you that as someone who was going through the process, even though it doesn’t surprise me that this is where I ended up, it was not always clear as to what the end outcome was going to be. Even though I had spent 7-8 years working on many of these side projects and side businesses, it was always something I did out of interest, curiosity and an ability to work with interesting and fun people. It was only when I began to think more deeply outside of the lines of traditional ways we view work and career that I saw that I could do this as my way of employment. But through a great set of mentors, proactively reaching out to and getting guidance from some incredibly helpful other independent creators and soloprenuers, and some changing shifts in culture and the workplace (see creator economy, solo capitalists, 1000 true fans, liquid talent) the time to go my own way seemed to be the best path forward. Not only could I have the chance to work on exciting and interesting things that I had always want to spend more time on, but I could do it on my own terms, and also, have the chance to do it while being close to my own family. The idea of being able to see my niece at her earliest stages of life while also spending unstructured time with my retired parents who I hadn’t seen in 15 months seemed too good to be true or to pass up.
Making The Shift to Entrepreneurship : How It Started How it’s going
When I decided to leave corporate, I had a rough idea of what I wanted to do, and that was to:
Earn income to pay the bills through known ways of services (consulting, training, coaching)
Create and build things during unstructured free time
Build credibility and expertise through content creation
Spend time setting up the business
Spend time cultivating relationships in my life, personally and professionally
Outside of that, I was open to what direction I wanted to go in. I am about 4 months into this journey, and so far it has gone incredibly positive. For now, here is where I am investing my time:
#1)Earning Income Through Consulting, and Training and Coaching
While I had savings, an emergency fund and generally speaking have made sound financial decisions, I also wanted to start earning some income to pay the bills and get more comfortable with solopreneurship life. Since I had some experience already with consulting, training, and coaching, I knew that these were viable options and they were things on my radar. However, to be completely transparent, I got into two of these things by happenstance or accident.
Early on in my life after Salesforce, I reconnected with two people who are very knowledgeable in the talent development and learning and development space. I had some thoughts that I wanted to do something in this space, and figured it would be great to get advice on how to expand my network into these fields. In both instances, at the end of the conversation these individuals asked if I had any interest in doing some consulting & advisory work for their companies. I honestly wasn’t even going in with the desire to ask for this, but over additional conversations it was clear that I had some skills and abilities that could add value for the problems they were solving. In this case, it was related to my Product Marketing skills, as well as my domain expertise in training and career development.
The second way I started earning income was through corporate training. Again, this was something on my roadmap. I had plenty of experience as a trainer/facilitator in the higher education space, and very much wanted and was planning to build up the capacity to do this for corporate clients. But I backed into this again, accidentally.
I decided to start a newsletter (this one!) a few months ago to write more about the future of work and implications for talent and career. As a result, I started writing a lot about these topics, which ended up being thought leadership which I used to book a number of corporate gigs teaching classes on career development, and have a few more prospective clients for next year.
Finally, I have been a leadership and career coach in the past but had put this on pause for awhile. I have a few clients that I am working with now that I have more time.
Next year, I plan on scaling the corporate training business and focusing on continuing to serve through an advisory capacity to a number of consulting clients.
To formalize this a bit more, I created my company, Betterwork Labs, which is a training and advisory firm that helps companies build better workplaces and leaders. I’ve taken a lot of the learnings and research I’ve done working with thousands of students and professionals, and built numerous offerings to help leaders and employees work effectively in our fast-moving world of work.
Note: if you’re looking for a corporate trainer or keynote speaker on topics related to career development, employee engagement, or hybrid communication, please let me know (Alex.Dea@gmail.com)
#2)Building the MBASchooled Community and Serving MBA Students & Alum with Professional Development
I’m continuing to build MBASchooled, and focused on two main areas. First, in terms of building out a community. Over the years, I’ve had the privilege of meeting hundreds of amazing students and alum, and I am finding ways to engage with these people and help scale their knowledge to a wider audience. This comes in the form of events, and through a monthly newsletter and a private community. My hope here is to inspire and guide MBAs in their own development and to encourage relationship building, learning, and development.
Second, I’m continuing to work with a number of MBA programs on various leadership and career development trainings, and have expanded to serving all types of MBA programs (Full-Time, Executive, Online etc) These are mostly virtual but will go back to-in person, and focus on helping students build the skills they need to succeed in the workplace. My aspiration is to have a core set of schools that I work with each year, and to have a robust set of offerings that I use with them to help as many of their students as possible. I started doing this with 1 school back in 2017, and am up to about 15 schools in the United States. I’m grateful for the ability to work with some world class institutions, and look forward to building those relationships in the coming year.
Finally, I am also scaling out and strengthening the content engine (podcast, blog, newsletter) both in the form of operations (getting content out the door without me doing all the work) as well as offerings and partnerships (corporate and school sponsorships.) My goal is to make MBASchooled the go-to-place for MBAs who want to uplevel their skills and accelerate their professional development.
#3) Staying sharp as a PMM and Sharing Knowledge in the Product Marketing Community
I learned so much as a product marketer, and while I am technically not one by title, I use what I learned as a PMM at Salesforce everyday in my job as an entrepreneur. As such, I want to stay sharp in the role, and have picked up a few paid consulting contracts doing some PMM consulting work.
Furthermore, I love the community that has started to build around product marketing careers, and I know that it can be a bit of a perplexing maize to break into the role. As a result, I’m trying to do my part in clearing this up for job seekers, and have been producing a podcast in conjunction with the Product Marketing Alliance on this very topic. Next year, I hope to expand into doing some more formal teaching and coaching on these topics. If this is of interest to you, please let me know.
Note: if you’re a current product marketer and want to chat about careers, please reach out. (Alex.Dea@gmail.com)
#4)Thinking, Writing and Researching For Ideas and Creativity
I have always loved coming up with ideas and creating things, but surprisingly, it's taken me till this point of entrepreneurship for me to actually realize how much I really like, enjoy, and quite frankly, need this. I think for a long time, I considered myself not to be creative because I wasn’t an artist. But realizing that creativity can be more than just being an artist and making time and space each day to think and build has been so incredible for my own well-being, engagement, and sheer productivity.
A lot of this ends up in google docs that never see the light of day, but it also appears in my podcasts, my newsletter, or in the conversations I have on LinkedIn and Twitter. Being a product marketer, I did have projects that required creativity and time to think, but I don’t think I fully was able to access that part of my brain until now. Now, with the time and space, and control over the time and space to be creative, I’ve been on a creativity tear. It’s been really interesting and a lot of fun.
#5) Teaching on the Internet
One of my longer term goals is to be able to divorce time from money and create revenue streams that are highly leveraged. One of the ways I think I can do that is by teaching on the internet. Online courses have been around for years, as have other forms of learning and professional development and I am beginning to invest in building out projects in this space.
This has mainly taken up time in the form of researching, honing my craft, and starting to build out content and ideas, as well as doing a few small pilots. I’ve gone down the rabbit hole of cohort based courses, digital products, and building online courses. I’ve also spent a lot of time thinking about my audience and who I serve. I have a few ideas for what I want to start, which include:
Starting side projects
Building an internal thought leadership platform within your company
Managing Your Career
Product Marketing Bootcamp For Aspiring Product Marketers
As you can see, it's a bit of an expansive list, but starting next year, I will start to winnow and narrow that down.
#6) Cultivating Relationships
I’ve spent a lot of time catching up with people I know who I haven’t talked to in awhile, chatting with people that I’ve met who are new, and just taking meetings with people who are doing things that I think are interesting. Some of these are for specific reasons (wanting to learn something) but others are for just ideating and gathering or potentially coming up with ways to work together and partner. Working solo means that if you’re not careful, you can end up being pretty isolated, this is one way in which I feel like I am still connected to something that’s bigger than myself.
What’s Been Fun
I have been thoroughly enjoying this experience. But if I were to get specific, here are a few things that I really like:
Creating - I love being able to create and build things, for myself, but also, for others. Having the time and space to do this has been really exciting. Whether it’s having time to create a podcast episode with an amazing guest, writing posts like this, or building a training deck for a client, I love being able to use my insights and thoughts, connect ideas and then convey them in a way that helps other people.
Free Time - Having free time every week just to read, research, write, think, ideate, etc has been incredible. I didn’t realize how much I valued this, until I got to have repeated weeks of interrupted time each week just to think and ideate
Choice - Having autonomy over my time, over my deliverables, over my clients, over my projects, has been really great. I love the choice of how I get to work, and who I get to work with.
Living in Los Angeles - Living in Los Angeles has been great so far. In addition to living here, I live within a 1 mile radius of my parents, sister, niece, and girlfriend. In a given day, I can go for a walk in the morning, work for a few hours, go for another walk, do a bit more work, and end the day having dinner with my sister and my niece, and do that multiple times a week. I’ve also had the chance to reconnect with friends who live in LA, as well as to meet people I met on the internet in real life.
Picking who I get to work with - Working for yourself means you not only get to choose your projects but also who you get to work with. I was always really fortunate to have coworkers I genuinely liked and enjoyed, and now that I work for myself I love being able to choose who I work with. This has allowed me to work in a professional capacity with some people who I really like, enjoy, respect, and admire, which makes the process so much more fun and meaningful.
What’s Not So Fun
Life is not all rainbows and butterflies, and there certainly are some downsides
Missing On Opportunities
One of my favorite things to do as a product marketer was to work with sales and to strengthen their toolkit as they sold million dollar deals to corporate customers. Being able to watch these people cultivate a relationship, communicate effectively, articulate and manage objections and challenges and patiently play the long game to seal the deal taught me so much. Now that I am in the solopreneurship business, I have gone from being the guy supporting the sales team to being the guy supporting the sales team and the sales team!
I booked my first paid workshop/speaking gig 7 years ago and earned $300 and remember to this day how nervous I was asking for that amount. I’m happy to say I have come a long way since then, and have built up what I think are passable sales skills. That said, I still continuously face rejections or things that don’t pan out. During the past year, I’ve had projects or speaking gigs that I thought were in the bag, but got cancelled at the last minute. I’ve had people reject my services and told they were too expensive, or not worth it for the level of experience and expertise that I had. I’ve had people tell me they were interested in working with me, and then after 4-5 follow ups, I still haven’t gotten a response back. These are not fun things to hear or take in, it can be really hard to not let these bother you or ruin evening.
Putting yourself out there
Fear of rejection is something that I have always really struggled with personally and professionally. Going the route of entrepreneurship means consistently putting yourself out there with the prospect of getting rejected each and every day. Two very real situations that tend to keep popping up with this are, first, getting rejected, and taking it very personally. Second, is not doing something because of the fear of getting rejected, and as a result, spending time analyzing it which in of itself causes fear and anxiety around the thought of being rejected (meta, I know.)
Feeling like I am behind
This constant feeling like I am behind. That I’m not moving fast enough, or not moving the needle far enough. These are moments of anxiety, of fear, of imposter syndrome, and are not so fun to deal with, but in almost all cases, are fleeting moments. The importance of running you own race at your own pace is something that I intuitively know.
Self-Doubt
The corporate path I was on I knew I felt pretty confident of what I needed to do and where I needed to go. When you get to go your own way, you gain the choice to choose your path, but because there is no mental model, or paradigm, it sometimes is harder to believe that you can actually achieve what you set out to achieve. Furthermore, I naturally sometimes just question myself and my abilities. The result of this is playing small, or shying away from an opportunity because we think we aren’t enough to handle it.
Not having my thing figured out
As a product marketer, I regularly focused on figuring out the answers to the questions
Who is our customer?
What problem do we solve?
How do we articulate our value clearly?
The importance of having tailored and specific messaging that demonstrated we knew who we were serving was all I thought about each and every day. As a marketer, I know that you cannot be everything to everyone, and that its important to speak to your audience and niche.
Unfortunately, I am still not entirely sure of who I am, who my main customer is, what problems I solve for that customer, etc. It is a little bit of cognitive dissonance of knowing that I am not doing the things I know I need to be doing, and accepting that it is where I am at right now. Part of this stems from the fact that I am early in my journey, and purposefully trying out numerous paths to see what resonates and sticks. But I still sometimes feel anxious or at least perplexed, because while I understand where I eventually want to be, I am not quite there yet.
Running the nuts and bolts of a business
I have a deep appreciation and respect for all of the small business owners and entrepreneurs out there who are excellent at their craft, good with customers AND know or figured out how to jump through all the hoops of starting a business. As someone who would like to think they are “smart” and at the very least resourceful (read: decent at google searching) starting a business is a lot harder than I thought it was, and takes a lot more time.
Filing paperwork, paying the right fees (so you don’t have to pay more) figuring out taxes, payroll, corporate credit cards, insurance, these are all mundane things that also (And if you’re a startup founder trying to build something in this space bless your heart) I’m incredibly grateful to all the other solopreneurs out there who have been kind enough to answer my questions or point to the right counsel or guidance because even in today’s age where there are literally millions of people who have started a business from scratch it still isn’t always easy or clear cut.
The Journey to Soloprenuership is Full of Learning and Surprise
Even with planning and intention, you cannot fully predict what is going to happen or how things are going to unfold. This path also appealed to me, because of the learning and growth that could come from it. Here are some of the things I’ve learned so far.
It’s Not just you - Being a solopreneur doesn’t mean that you do all the work yourself. In fact, it’s the opposite. It’s recognizing what you have to give up, or let others do because you are being thoughtful and intentional about the work that only you can do. This has been hard for me, as I feel like I need to simultaneously take proactive ownership while also prioritizing my time, but it's a good lesson to learn for anyone who is trying to go out on their own.
I thrive in creative environments - I have thoroughly enjoyed the chance to have time and space to think, ideate and create things. I have never considered myself to be a creative person, mostly because I have always associated creativity with art. But having control over my own schedule and time has allowed me to think expansively and turn thoughts and ideas into more concrete deliverables. The amount of energy and excitement I get from getting to do this was surprising to me, which goes to show you that even when you are self-aware and self-reflective, there’s still a lot of yourself that you sometimes fail to see!
Emergent Opportunities Will Arise - While some of the first few official paid projects and gigs I’ve gotten have come through things I planned in advance, a number of them have come as a result of serendipitous encounters and emergent opportunities. I was able to use this newsletter to build a few relationships that led to training workshops. I connected with an old colleague who connected me with one of her former employers who needed help. I’ve met a lot of smart and thoughtful people who I’ll continue to connect with over the next phase in my career.
I need alone time to think - While I loved the hustle and fast paced nature of corporate environments, one thing I didn’t realize I needed was alone time to think. Again, as someone who has always been self-aware, I know that I thrive in team-based environments and around people. What this experience has taught me, is that while I do love those environments, I also need dedicated space to be by myself to think, process, and let things sit. During the past 5 months, I’ve spent good chunks of my day by myself, on walks listening to music or podcasts, or just sitting in silence, and it has helped me clear my mind, synthesize my thoughts, and become more thoughtful about what I want to do.
What’s Ahead
As I get to the end of 2021, I’m happy and proud of the decisions I’ve made, the impact I’ve created and excited for what’s ahead. I’m also incredibly grateful to the many of you who have supported me in so many ways on this journey. The tagline to my book is How to Make The Most of Your MBA Experience because I think I’ve been asking that question to myself, not just about the MBA, but about life in general.
For me, making the most of my life experience is about building and creating things that positively impact others, spending time with friends and loved ones, and using my talents and skills to help other people be their best selves and positively impact society. My journey to solopreneurship has allowed me to do all of that and more.
At the end of 2020, I took the last two weeks off to recharge, and get ready to come out of the gate hot for 2021. While I don’t think I expected all of what was to come, I end the year incredibly grateful and happy for how things have played out, and even more grateful for the ability to lean heavily on others as I navigated through the ups and downs of this year.
For those still reading, if any of what I am doing sounds interesting and if you’d like to work together in a consulting, training, or keynote speaking capacity don’t hesitate to reach out.
And to others, if you are currently thinking about taking a break from work for personal or professional reasons, or potentially pursuing a path to solopreneurship my DMs are open. I would love to be a sounding board.
PPS.
I’d like to give a shout out to the following people (and their respective products/resources) who have been instrumental in helping me on this journey. If you are thinking about making a leap to entrepreneurship or trying to build or create something or just want to learn more from smart and thoughtful people make sure to check these individuals out.
Excellent article Al! Super interesting, and I'm rooting for you in 2022 & beyond!
Surprised Woj didn't break the news first. Great post.