Celebrating 2 Years of Entrepreneurship

Reflections and learnings of 2 years of making the leap from corporate to entrepreneurship

This week is the 2-year anniversary of leaving the corporate world and starting off on my own journey of entrepreneurship, running my own leadership & talent development consulting business, and the multidimensional job of being a facilitator, podcaster, speaker, and community builder. 

One of the fun parts is reflecting back on all the things I get to do, and how various seeds and snapshots of these opportunities were planted long ago, but are now coming into life and into focus. 

As a kid, I grew up going to conferences and events, and watching the leading management thinkers share their ideas on stage. I remember asking my parents and family about what it would take to get to do something like that. And methodolically over the years, I got brief glimpses of it, to now, where I get opportunities to do that today.

My first job, working at a golf course gave me the chance early on how to manage people when I was just a teenager, and while the stakes and context is certainly different, I spend a lot of my days teaching managers how to be good managers today.

And even with writing, podcasting, and blogging - those seeds are most evident with starting MBASchooled, but even back when I was in college I began to see the power of sharing ideas and information to communicate with others.

In college, when I ran for and became student body president, part of my platform was around using technology (at the time facebook, twitter, and youtube) as a means to better connect and share how the student government was going to work for the students BTW: If you want to see a fun video, check this out.

And all the scrappiness and resourcefulness from the successful and not successful entrepreneurial ventures (selling potato chips at lunch, selling t-shirts to my freshman classmates through our class facebook group, trying to start a driveway sealing business) have come in handy as I’ve tried to build my business today.

I often get asked by newer entrepreneurs or individuals working in leadership positions who are working in a side business/side hustle situation as a coach, consultant, or creator what it’s like to make the jump, and I feel grateful when I hear that my story has been useful and helpful to others, so I wanted to share a few learnings I’ve had from the past year of my journey.

#1) Values Create Value

As an ex-consultant, one of my go-to playbooks when I have to do something is figure out what the mental models, best practices, frameworks, and then to go implement that for myself. 

Over the past two years, in some instances that has worked pretty well. You don’t need to reinvent how you decide to file your taxes or selecting a website host, and there’s a case to be made that not reinventing the wheel of what millions of people have already done in starting a business is an efficient and best use of your time.

But there are other parts of business and my business where after looking at the best practices and frameworks, I realized it just didn’t land for me, or it honestly felt like something that I couldn't do. But I still had to do that thing - be it sales, marketing, content, podcasting, etc. I wasn’t going to not do it, (you have to sell if you want to eat)  so in those moments where I couldn’t follow the best practices or the frameworks that others told me to follow, I just tried the best I could to find an action that aligned to a value of mine and then to act in that way. 

So far, I would say that I’ve seen some positive results. Many of these things involve my own ideas and how I do business, and in many ways I think it helps because ultimately, the nature of my business is connecting with other people, either through my ideas, services, or just general nature and disposition. 

When you act in a way that shows your values, you get a chance to show someone else who you are, what you stand for and what it might be like to work with you. This has come to roost for me a number of times in the past few months where I’ve connected with people or businesses and gotten opportunities. In each of these circumstances, instead of the traditional route of trying to get the business, 

I just acted in a way that was more aligned with one of my values, and I started seeing positive results. In some cases, some of this requires a bit more of a longer game approach, but I also think that it creates conditions for me to deliver more impact, which I think will eventually lead to a greater ROI. Morever, the feeling of being able to integrate your whole self into who you are and how you conduct your business cannot be underestimated.

#2)Making time for creativity

One of my frustrations with my last few corporate jobs was that I worked in roles that were inherently creative but never got to be creative mostly because there was literally no margin in my day.  As Cal Newport calls it, the hyperactive hive mind that sometimes takes over knowledge worker life basically killed any sense of creativity I could have, save a few exceptions. 

What’s been interesting and fun to me over the past two years is that I’ve actually learned I not only am creative, but I really like creativity. Being able to create margin in my calendar each day, where I actually have time to think, has unlocked a level of creativity and output that I don’t think I realized I was capable of. Whether it’s the fact that I’ve shipped over 100+ editions of this newsletter, started a new podcast, or come up with new ideas for frameworks and POVs in my consulting and training work, realizing that I’m not only a creative person but that I can embrace this creativity is exciting and unlocks a whole new kind of possibilities.

Many corporate jobs emphasize and encourage repeatability, standardization and efficiency thanks to our guy Frederick Taylor – While I’m not suggesting that approach doesn’t matter, part of why I chose this path was so I didn’t have to always rely on that approach to getting things done, so finding other ways to lean into the things that make you uniquely you is something I’ve tried to implement when running my own business.

#3)The balance of autonomy & choice 

Having autonomy is great, but what’s also been challenging is learning how to use it. I’m fortunate that there are times when opportunities come my way. There’s always a challenge of figuring out what to say yes and no to (and then the feeling of FOMO that comes with it.) 

In this kind of business there are so many potential paths - consulting, advisory, training, coaching, keynote speaking, productizing your work, writing a book, doing partnerships, running a course, the list goes on. It’s awesome that so many of these things are on the table, but how do you choose?

But there is also another challenge with this, and that is about not just what you decide to pursue, but how do you know if it’s working, and if it’s not working, what do you do? Do you keep going, give it more time, “fail fast” and move on?

I experienced a lot of this earlier this year, when I tried a bunch of new things when business was dry. In my old job, if something wasn’t working, I had some judgment on how to evaluate it but I also would hear about it from my boss or another leader. 

You don’t have that mechanism anymore because you are the boss, so it requires a lot more judgment. The tension here is the false positive - cutting something off too short before it becomes effective, or letting something go on too long and wasting precious time or resources. This at its core is the essence of entrepreneurship, and I think it does come with experience.

#4)Learning how to say no

As someone who is in a profession that is very online and that naturally means connecting with others and sharing my ideas, I am fortunate and grateful that I get a lot of opportunities that come my way, and more specifically, introductions to individuals and people who reach out. This in many ways means that the work you are doing is working because people are associating you with hopefully opportunities that are aligned to your goals. 

While this is great, it can often feel overwhelming, and even draining. This is especially true as a people pleaser, and someone who believes in generosity. This is probably the thing I am struggling with most at the moment, but I’m learning and leaning into learning how to say no, be graceful and compassionate and also how to advocate for myself and what I need. 

#5)The tension is the point  

Most days I either feel like I’ve got it all figured out, or that I am 27 steps behind where I want to be. Oftentimes it feels like there is no in between. This tension used to bother me, and to a certain degree, it still does. I want to speed up success, mainly to feel secure in my life for myself and for my family, but unfortunately life business doesn’t really work that way. In those moments of tension, I am trying to lean more into them and pay more attention to that feeling. In those moments, instead of trying to solve for the 26 steps I’m behind in, I really try my best to figure out what is the 1 step forward. This is not easy, but it's important if anything for my own self-preservation 

#6) Your Career is a Team sport

One of the most important career lessons I’ve learned is that your success is often correlated to the amount of people who want you to succeed. The perk of working at big companies is that there are people anywhere, and at places like Deloitte and Salesforce, I always knew people willing to help. I’ve had to reinvent that infrastructure now I’m on my own (although grateful for my colleagues who still return my emails!) - Building a new set of relationships has not only been helpful for my business, but for helping me grow, as a founder, podcaster, writer, speaker,  person, friend, sibling, cousin, husband, and colleague. In a world that feels at times so disconnected, business is still a wonderful vehicle for learning.

Conclusion: Embracing The Messy Middle

Scott Belsky, Founder of Behance and CPO at Adobe, wrote a book called The Messy Middle which explains that chaotic and ugly process after you create a startup, business, idea, and before it comes to life. In many ways, I feel like my business is in the early innings of the messy middle. 

The potential and promise is there. It’s like the clay is all out on the table and there is plenty of canvas, but it's still in clumps and not fully formed. I can see the potential and possibilities, and now comes the messiness of figuring out how to shape and form it before it goes into the fire and becomes a final product.

My observation is that there are two approaches to navigating the messy middle. Approach one is to power through it, just suck it up, pound through and exert your will and skill until you get through the middle.

The second approach is to embrace the messiness, and use curiosity, patience and creativity like an artist to learn your way through. I don’t know if one is better than the other (I think both can work?) but I am much more of a type two person. I see all that’s there and the possibility, so I’m going to do my best to embrace it.

When people ask me how my business is going and if I am happy with the choice I made to leave the corporate path, I often tell them two things that seem contradictory.

1. I can’t believe I waited this long - I am really enjoying what I do, and doing some of this as a side-hustle for almost 7 years was great training ground, but wow, why couldn’t I have woken up sooner to how awesome this was and made the leap even sooner!?

2. I wish I could have worked in corporate longer - Not having a steady paycheck, worrying about cash flow, and dealing with rejections and dead ends with opportunities and income is really hard. Also, I just got married, and live in Los Angeles, so it would have been a bit nicer to have a few more years of nest egg saved up under my belt

I think all this really means is that I made the switch at the time that was right, and my hope is that these lessons of entrepreneurship and business that I’ve learned are ones that I can continue using to choose work and build a business that leads me to my own path to success.

That’s all for this week. Thanks for reading!

Al