A Belated Post-Mortem of My Entrepreneurial Journey

By Deena Englander @ 2023-06-23T21:52 (+32)

I was recently recalling my early days as an entrepreneur, and thought I’d share my post-mortem thoughts on what I wish I’d done differently.

For background context, I currently am a business coach and workflow optimization consultant. I help organizations run more effectively and provide skills training by way of the EA operations fellowship.

When I started out on my own, I chose to be a solopreneur because it fit my lifestyle well, and I had the technical expertise to be able to do well. That was all true, but what I didn’t have was experience being an entrepreneur. I had the mentality that I could learn anything from books and research, and that if I put my mind to anything, I could make it be successful. And although I still believe that is mostly true, I now believe even more in asking for help to compensate for my weaknesses, blind spots, and lack of experience in whatever areas I need help with.

Although I ultimately succeeded as an entrepreneur, it was a pretty challenging and draining journey. It burned me out on so many levels. I made so many costly mistakes. I didn’t know what networking meant or why I needed to do it. I didn’t know how to create a strategic plan to develop my business, so it took a while to gain the traction I wanted. In a notable instance, I had to refund a client’s fees because I was clueless about the contractual legalities and didn’t have a good lawyer then. Ultimately, I did learn a whole lot and gained a lot of expertise as I went through it – but it had a big price: my mental and physical health, burnout, and a much longer timeline to success, profitability and impact. I’m still recovering from that all (it’s even harder as a mom post-pandemic!), but I’m still thankful every day that I have the lifestyle I want and I can earn enough to support my family. I just really wish that I had had more support back when I started.

My current “theology” on business/organization success is that its leaders need three core things in order to succeed: 

1. Access to relevant knowledge and education (books, podcasts, mentors)
2. Having accountability partners (this can take the form of coaching)
3. Being part of a supportive community (online or in person, networking groups, friends)

I had #1 – lots of education and books. 

So why didn’t I get the rest of the support that I needed? Well, I was thrifty, in a silo, and slightly arrogant in that I thought I could learn everything from books. While I did learn a lot from books, nothing can replace real-life experience. That taught me so much more. I wish I had had someone guiding me, telling me what made sense and what didn’t, what traps to avoid, and what to focus my efforts on. I had no social support either – I was the only female entrepreneur that I knew in my religious community (which we’ve since left) and I had no idea how to tap into the secular network. I was a trailblazer and proud of it, and I felt that I didn’t need help and definitely didn’t want to pay for it. Now I realize how much of a mistake that was, and I make sure to surround myself by experts who help me achieve my fullest potential.

If I could go back and tell my 23-year-old self how to be smarter about the process, I would have told her to join some networking and business development groups. I would have told her to get a business coach to help develop ideas and create a good, profitable, strategic business plan. I would have pointed out the higher margins of profit, impact and stability that I would be likely to see if I had expert assistance.  It would have been so much easier, so much healthier, and so much more impactful if I had the right guidance early on in my business development.

The bottom line is: Surround yourself with support. Get mentors. You’re not alone and you shouldn’t be. 

It doesn’t matter whom you use as your mentor or coach – it matters that they understand your industry and goals, that they connect well with you, and that you trust each other. It’s often important to seek paid help instead of pro-bono, because then you’re both invested in the relationship ^[1]. If you’re focused on a cause area and think that it’s important, then it deserves your investment of time and resources to make as impactful as you can get it to be. And for that to happen, you need your community of support people. People doing similar things, people in mentorship roles, people who have similar challenges – they’re all important. If you want your organization to be successful, the “one thing^[2]” you can do to help it is to give it the right support and direction early on.

I’m happy to chat with anyone who has any questions, or if you’re looking for a coach – I represent all the members of EASE (and myself) and would love to get you set up with the support that will make all the difference. Feel free to pick a time on my calendar or send me a PM or email. 

Good luck on your journey!

1. ^{^}

   Pro bono is definitely acceptable in some cases; I take a few pro bono cases myself, but not more than 1 or 2 clients at a time. Often, though, the client takes it less seriously since it’s not as costly to them. And good providers should be earning money off their practice, so you’re less likely to find a pro bono coach.

2. ^{^}

   What is the ONE thing that you can do that will make everything else afterward simpler or easier? Based on this book or read up on the theory here.