A Glance Back at SOBCon

I just returned from my fourth SOBCon event in Chicago, and, as usual, it was a whirlwind of great ideas and non-stop networking.

I love SOBCon – the intimacy, the transparency, the practicality of it. Get a bunch of smart, motivated people in one room and watch the creative ideation flow.

SOBCon panorama

For me this year, SOBCon week also marked the launch of my new website, SteveWoodruff.com, which emphasizes a message close to my heart: Discover Your Fit. After several years of helping people and businesses figure out their professional direction and marketplace and message (their “fit”), it was time to take this whole Clarity Therapy business up a notch by launching a professional site.

And, as I spent time networking with dozens of people at SOBCon, it was reinforced again and again how challenging it can be for any of us – all of us – to gain a clear business focus. This is not an abstraction. It’s a sitting-across-the-table-and-listening-to-genuine-pain issue.

So, instead of giving a re-cap of the speakers and topics from SOBCon (I’m sure others will be doing that), instead, I’m going to mention the very human needs of people with whom I was able to rub shoulders. Their experiences struggling with business direction and growth parallel what I’ve seen everywhere else.

  • Life earthquakes. Sometimes, we make a modest strategic pivot in business direction; but other times, big changes are thrust upon us, making us re-evaluate the entire picture. A couple of these situations came up. These can be very upsetting times, but also can provide the groundwork for great advances. Our ears are uniquely open during these more traumatic times to consider fresh direction.
  • Swinging outside the strike zone. I talked in-depth with one person who is so client-focused, that he/she loses focus on staying in his/her true sweet spot. When we try to do too many things, we often leave our most differentiating wheelhouse, and get into the weeds of doing too much less-than-profitable stuff. People with very high expectations and a bit of a control-freak mentality fall very easily into this. It can turn us from someone with specialized offerings, into a commodity player without enough bandwidth to grow into new clients.
  • Waiting for permission. It definitely took me many years to get over this. Many people I talk to are hesitant to claim their ground, to declare their differentiator, to own their own niche. No one is going to give us permission. Just do it. People want to follow confident, forthright direction. You have permission (if someone asks for your permission slip, just point them to this blog post!)
  • Ready – Fire – Aim. We often let our clients choose us – instead, we need to choose our clients. One long SOBCon lunch conversation went deeply into targeted marketing – identifying your ideal client and pursuing that niche, rather than just taking whatever comes along next. Huge issue for small businesses/solopreneurs – our focus often gets muddied right here. A successful approach includes clarity on both offerings and audiences.

One of the coolest things incorporated in this year’s SOBCon was the “Hot Seat” sessions, where event sponsors presented their most pressing challenges, and the audience gave on-the-spot input that was often uncomfortably relevant and targeted! During the many Mastermind sessions, this was happening on a smaller scale with all the attendees at each table. Tapping into the creativity and brainpower of talented, business-savvy people is what SOBCon is all about.

And maybe I was just more highly-attuned to the subject myself, but it seemed that there was quite a practical emphasis this year on good old e-mail as a marketing tool. It’s never really gone away – but I know my experience has been that e-mail has always been the most effective digital communication tool I use to grow my business. You?

It was wonderful to see SOBCon co-founder Liz Strauss participating (Liz is recovering from cancer treatments) as much as she did; and, as always, Terry “Starbucker” St. Marie did a great job orchestrating and leading throughout the weekend. But SOBCon is much more than its leaders and featured speakers. It’s a community of people supporting one another. If you just want to passively listen to a bunch of gurus, there are plenty of conferences for that. SOBCon is for thinkers-doers-dreamers-lovers.

Here is Mike Hale’s review of his first SOBCon experience

Some great SOBCon photos from Shashi Bellamkonda



  1. Great approach to your recap, Steve. It was good to see you even though we didn’t catch up. I love the way you reframed the lessons you took away from the experience in terms of the participants and not the presenters. Congratulations on the new site, too. It’s a winner!

  2. Wonderful recap. Congrats on the launch. Your takeaways here are wonderful. I will take one for myself – thank you for the permission slip!

  3. Well done, Steve! You captured the big issues and challenges we all were facing. I too loved the vendor hot seat sessions and thought they got unbelievable value for their sponsorship. Talk about ROI! Some of the smartest people I know were in the room giving their best advice. Pure gold. I think the group probably saved one of the start-up sponsors 18 months of flailing around in the marketplace.

  4. Thanks for posting the great recap! It’s cool to see things from a SOBCon regular’s perspective too. I came away with a lot of ideas and inspiration to really focus on my business. Looks like launching a new blog was part of that plan for both of us! Looks great and I’m looking forward to reading more from you.

    And a big thanks for the link to the review on my blog! I added one back here too so hopefully people can get both takes on a great event.

  5. Loved your recap Steve! We definitely took similar nuggets away. My favorites were being clear on who we serve rather than catering to everyone and that good old email list. I know I love my subscribers 🙂
    Great website by the way!


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