Reflections on my 2023

Reflections and takeaways from my 2nd full year of entrepreneurship

TLDR: This is a longer post on my year end reflections on 2023. If that’s too long for you, check out my latest podcast interview with Steve Hunt

2023: a Year in Review

I’m getting to the end of my second full year of being an entrepreneur and running my leadership and talent development consulting practice. I wanted to take some time to reflect on the year, what I learned, and what I am thinking about next year. (If you want to read mine from last year, it’s here)

First and foremost, this year I got married. This is a big life milestone. My wife is my biggest supporter. She always listens to all the things I have to say about my work (and work, broadly speaking, meta.. I know..) and provides me with coaching, guidance, support, encouragement, and unconditional love that I am forever grateful for.

While I have no doubt in my mind that I worked hard to get to where I am and made sacrifices and intelligent decisions, I also know the privilege I have of being able to get to do the work I get to do, A big part of that is in having a supportive partner who not only believes in me, but is willing to make space and sacrifice because she knows how important this is for me. I don’t take that for granted, and feel a deep sense of gratitude to her. I would like to think I am a supportive partner in return, but have the rest of our life to keep working at it!

The Beginning of The Year: If you don’t sell you can’t eat

Overall, I’m happy with how the year turned out. I will be honest and say the year started off pretty challenging, but I am very happy with how I rebounded.

On January 1st 2023, I woke up and went to my computer, opened my to do list and looked at my calendar and I had this sinking feeling - There was literally nothing on my calendar or to do list. I had nothing on the books for the month of January. I wondered why not, and then I realized that I had made no effort to drum up business in the 3 months prior! This was definitely an oh shit moment.

I wasn’t sitting around during those 3 months, I had a busy and packed schedule. But it was a wake up call and an important lesson in the life of being a solo business owner - If you don’t make time to prioritize business development on a regular basis, don’t expect things to magically show up on your lap.

To top things off, the year started off slow, due to headwinds in the economy. And given that my clients were in the technology industry, one that got hit hard by layoffs, things were looking pretty grim.

But I did my best to make lemons out of lemonade, and decided to take action. I decided to invest in building online courses and finding opportunities to teach online, as well as in looking into my immediate network for introductions to people who might be interested in my services. 

One of my core beliefs in life is that if you don’t know the answer to something someone you know probably does. I also started reading, consuming, and learning anything I could about sales and business development. I talked to other trainers, speakers and facilitators who were seasoned professionals.

I connected with old colleagues who worked in selling professional services to learn the ins and outs of pricing and packaging. And talked to veterans and whomever would take my call who had previously worked in an HR leadership or consulting role, to get their perspectives on how to best position myself in the market. (If you responded to my text, email or Linkedin message, thank you!)

 

Business Starts to Appear

The results of my actions didn’t come right away, but after a few months, I started to see progress. As time went on through the year, some dominos started to fall into place. I had existing clients who I asked to refer me to other potential clients, and got business that way. After a few workshops I did, I had a few attendees make introductions without me even asking people they knew in their network. 

And through connecting and relationship building with existing people in the HR and talent space or through new relationships I made, I started to see some progress. While I have yet to perfect business development and sales, I went from nothing to something, and feel confident that through consistent habits and improvement, I’ll continue to get better. Above all, I learned that I actually A) wasn’t bad at business development and B) I sort of like it! I feel excited about the possibilities and opportunities ahead.

Being an Opportunity Generator

While I was hard at work working on my business development skills, I did what I could to make the most of opportunities that came my way. Each moment you deliver something to others, is your opportunity to unlock your next opportunity. I said yes to things when I wasn’t entirely sure if I should say yes, and went the extra mile to follow up or make a connection with someone who attended my training, someone who connected with me on LinkedIn, or a colleague I knew who cared about some of the same things that I cared about.

In basketball, certain players are known for being able to “get their own shot” meaning, they don’t require anyone else to get offense going, they just can do it themselves. Being an entrepreneur is somewhat similar. You need to be your own creator of opportunity. And in a professional services business like mine, that means getting out and in the hearts and minds of other people.

Some of this can be done digitally (thankful for Linkedin and other media) but some of it comes through old fashioned being in front of people or at least top of mind to them. We do business with people we know, like and trust. So you have to find ways to make yourself known, likable, and trusted. I tried all sorts of things to do this this year. Hosting events, connecting people, doing workshops, attending conferences, doing research, connecting with people on Linkedin. Some of these worked, others didn’t, but I learned a lot and made some great relationships along the way.

Meeting Lindsey Pollak IRL was one of my highlights!

Enjoying The Journey While You’re On The Journey

The end of the year has been a sprint. I came back from my honeymoon in October and it’s been a never ending string of commitments to deliver on. October, November, and December were a series of conferences, in-person trainings, keynotes, virtual trainings and client kick offs. These were all good things - these are the exact opportunities that I want and need in order for my business to grow - and being able to show up and deliver great work plants a seed for the next opportunity. 

That said, it is challenging! There are lots of moving pieces and balls that I feel like I am juggling in the air. The past 2 months at times have felt like a grind. I had to tell myself multiple times during those moments to make sure that I didn’t lose sight of the moment, and really pushed myself during that time, to take moments to appreciate and enjoy what I was doing.

This hit me back in October. I got the chance to meet Lindsey Pollak, the keynote speaker, NY Times Best-Selling Author, and Career & Workplace Expert. I’ve gotten to know Lindsey virtually over the past few years, but this is the first time that we met in person. When I was 22 and fresh out of college and floundering in my job, I found Lindsey’s first book, From College to Career and began reading and following her work. As I got more into the career and leadership space, she was always someone who I admired and looked up to from far away, and even more so, when I got into this line of work, and started being able to contribute my own ideas and perspectives in this space. Lindsey is a pioneer in the career & workplace space.

I know I am here because of people like Lindsey - but to have that full circle moment, of being that lost 22 year old trying to figure this work thing out to having a career where I get to research and advise on work and then to meeting and talking shop with someone who you truly admire and respect and feeling that mutual respect back, was so humbling and meaningful.

I am really trying in those moments to also breathe and to observe the opportunity in front of me. I worked to get to this point to do this kind of work because I wanted to do it and I enjoy it, and I don’t want to just let it pass me by. So I am doing the best that I can to honor that, and to enjoy the experience while it is in front of me.  Doing work that is impactful and meaningful is a privilege, and one that I’ll fight to ensure that as many people have the possibility to get.

Overall it was a good year! That’s the headline. Despite the rough start, the year ended up well, and I feel excited about what’s head.

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What Went Well

• Bouncing Back From a Slow Start - When I had my oh shit moment when I realized I had no business to start off in 2023, I didn’t panic or feel sorry for myself, but rather, took action. I leaned into what I knew how to do, which was to learn as much as I could on my own, ask for help, and try things. I am ending the year up in revenue from last year.  I attribute that to my willingness to ask for help, learn and grow.

• The Edge of Work Podcast - I’m proud of the podcast. The idea behind it, as well as the effort and craft that I’ve put into it. On numerous occasions, I’ve had podcast guests say to me, “that was a really great interview.” In many of those cases, that feedback came from people who are on a lot of podcasts. While I still think the podcast has a lot of room for growth, I am proud of the intentional effort I put into something, and for starting a movement around it that seems to be resonating with an audience.

• Relationships - Being in business for yourself means you get to work with people you want to work with. I’m so grateful for the relationships I’ve made, both clients and partners. It truly makes this work worthwhile. Many of these came from just reaching out to people, people I met at conferences and followed up with or people I met online. I will always be grateful for the friends and colleagues I worked with when working in big corporate companies, but I’ve had so much fun building my own web of relationships now that I ma on my own.

• Speaking Engagements - I’ve had a number of speaking engagements that I’m especially proud of. Over the summer, I had the main stage at a conference that my Father used to speak at. In December, I did a keynote and a panel on a topic I’m passionate about. I grew up going to conferences and seeing speakers speak on stage and wondering what it took to do that, and have been working ever since then to get that opportunity and here I am. I don’t take that for granted and I cherish that deeply.

• Inspiring Others - I’ve received a handful of messages, emails, texts from people, some who I knew, others who I didn't know who wrote to say that something I said, wrote or spoke about, inspired them to do something or take action. To know that I made an impact is why I do the work I do, and is something I don’t forget.

What Didn’t Work Well

• Comparison Traps - Comparing myself to other people who are farther along or more successful. This game never ends, I think I am getting better at managing it, but it still sticks around.

• Rejections - Submitting proposals that got rejected was not fun. Nor was getting asked for proposals just to get ghosted, or get told that there was no budget. Not getting responses to outreach that you do, none of these things are fun nor easy to manage. While I accept that they are part of the process, it does not make it easy!

• Managing Priorities - Even though the idea of prioritization is simple to handle, it does not mean it is easy. One aspect of this is managing the priorities at hand, the other aspect of this, is figuring out what to prioritize. How do you know if it should be project A, or or project B? There’s always the fear that you choose wrong, which sometimes can also paralyze you from taking action. While I can’t point to any specific examples, these are all regular challenging thoughts in my head.

• Legal Issues - I got hit with some legal issues in the beginning of the year from another larger organization that is in my industry. This was not a fun process. Without getting into details, it taught me the importance of doing business in a way that aligns with your values and that makes you proud of the person that you are. And in many ways, it was reassuring in that I ended up talking to a number of other founders and business owners who went through similar experiences.

• Teaching on the Internet - I set a goal for myself to invest time and effort into teaching on the internet. My two main ways of doing that this year were through a course I made for Udemy, and then through teaching on a learning platform. While I was able to execute on both of those things, the results did not go as well as I hoped for. My Udemy course netted me a total of $3.62 (womp womp!) If anything, it just underscored to me how hard it really is to scale by teaching courses (live or digital) on the internet. I’m not ready to give up yet, but it does confirm yet again just how challenging it is.

• Business Development Planning for 2024 - As a result of what happened in January, I made an effort to start planning for 2024 as early as October 2023. However, I got so busy with work that I needed to deliver in 2023, that many of my well-intentioned plans got sidetracked. I wouldn’t call this a failure by any means, but it didn’t go as planned or as I would have hoped. There’s room for improvement, but I will say that I am making steps in the right direction.

• Cognitive Overload - I had too many days where I had too many back to backs and too much context switching. I need to be better next year about spacing, as well as just saying no to more things and yes to fewer of the right things

Takeaways and Learnings From This Year

• Your Learning and Career Growth Fuels Your Business Growth - For as much work as I do in teaching leaders how to grow their careers, I’ve had to heed a ton of my own advice this year. The reason I was able to succeed this year was because of my willingness to learn and grow. Basically, the growth of your business is tied to how much you're willing to learn. What got you here, won’t get you there. I’m leaning into this, as I think about how I want to continue evolving my business.

• Creativity is my accelerant - When things are off for me, it’s when I haven’t had the time to write, think or be creative. I’ve realized that I need to make time and create space for this. Additionally, I’ve also realized I can be judicious with my creativity. While it’s laudable to show up as consistently as I have across many channels, I think I underestimate how much I actually needed to do in order to be visible. I’m going to work on streamlining this for next year

• Small things can make a big difference - Some of the opportunities that came my way this year, be it a paid engagement, a connection or some other creative project came from doing something small that made a big difference. After a keynote talk I gave, out of the 200 people one person reached out to me to ask to meet with me to chat about my career. They ended up bringing me 2 business opportunities. Another person I hosted on a podcast, after the podcast was over, we talked for 10 minutes about life, and she introduced me later on to one of my biggest clients. Sometimes the small things can make the biggest impact.

• The best time to plant a tree is today - A number of opportunities that happened this year came from things that I started in 2020 or 2021. Sometimes, things just need time and space to marinate. It's hard to know when things will pan out, but it just speaks to the importance of being an “opportunity generator.” The more you put yourself in those positions the more opportunities can come your way.

• Keep Leaning on What Makes you Unique - As much as I do rely on learning from and with other people, I’ve tried to balance that with acting and working in ways that are unique to me. Whenever I do that, I tend to find that I attract other people who share the same ethos or perspective, and that leads to the chance to associate with other people who share my value system and mindset.

  

Questions For Further Reflection

Now that I’ve been doing this for 2 years full-time, I feel confident that I have something that is working. I’m not close to my aspirations, so I have a lot to learn and ways to go. Here are some of the questions I am thinking about and pondering:

• How do I make a bigger impact doing less things?

• How do I improve the pricing and packaging of my offerings?

• Should I focus more on just improving what is working, or are there structural changes that I need to make to get to the next stage of growth?

• How do I become more consistent with business development?

• What’s the right amount of “slack time” to put into my schedule?

• Do I want to take the months of July and August off? If so, how does that affect my 2024 planning?

• As a solo practice, how do I find ways to find leverage in my work?

• What are the creative projects that I want to focus my efforts on?

Goals For Next Year

I’m still in the goal setting process, but here is the rough breakdown:

• Retention + Expansion - I have a specific list of existing customers that I am working to grow revenue in for next year

• Simplicity - Streamline content and thought leadership efforts. I’ve enjoyed all of the places (newsletters, podcasts, LinkedIn) but I need to streamline and focus. I’ll also be launching a website for all my my streamlined content in Feb ‘24.

• Do Less - I want to focus on “few things well.” I’ve identified the highest best uses of actions I can take, and am going to focus on doing those as much as possible, and getting rid of everything else

• Take Time Off - True to Parkinson’s Law, I’m hoping to become more efficient and impactful by imposing time constraints.

Conclusion

In two full years of entrepreneurship I am proud of the work I’ve done and excited about the road ahead. I have a lot to think about and ponder for how I can continue to grow this business, but in the meantime, I’m going to keep trying to appreciate all the moments on the journey.