Is your small business in the awkward “tweens?”

Not too small, not yet big – right in between
If you started out as a solopreneur, then you probably think back on that time as “the good old days.” It might’ve seemed crazy at the time, but in retrospect it seems quite manageable, doesn’t it? Because there were fewer moving parts. You had only one income to worry about, not ten! And looking ahead, perhaps you hope to have a much larger operation someday, with professional managers looking after all parts of the business. 

Until then, it’s lonely at the top time. You’re the entire leadership team, serving all the key business roles, like finance, marketing, sales, operations, HR, R&D, etc. I call this stage, the “tweens.” As with kids, the tween years are that awkward stage, where you’re not a child anymore, but not quite an adolescent. You’re in-between. And nobody ever trains you for the in-between stages.

Being a “tween” involves lots of drama
Symptoms of being in the tween stage include:

  • You have more business than you can handle…but just can’t say no
  • The company is undergoing near-chaotic levels of change
  • Cash flow is unpredictable
  • Truly delegating to staff is still easier said than done
  • You haven’t yet hired managers in finance, operations, sales or HR
  • You spend lots of time helping staff be productive
  • You still bill hours a lot yourself (especially if you have a consultancy with your name on the door!).
  • Evenings and weekends are for working on the business: sending out invoices, bookkeeping and catching up on correspondence
  • You’re feeling stress at home because the business is on your mind 24/7

Good news: being a tween is entirely normal
If this is your situation, it’s important to know that you’re not alone. And you’re not doing anything wrong. This is simply how life is for the owner of a tween business. But there are some things you can do to grow your way out of this phase. 

Three steps you can take to “grow up” more quickly

  • Talk to other small business owners – None of us have have all the answers, but we’ve each figured out something. I’ve found that every owner and founder loves to tell war stories and has a few hacks to share. And at the very least, commiserating with someone else who “gets it” will provide you with a much needed shot in the arm.
  • Create an advisory board – Since you’re the entire leadership team in one person, you need mentorship and advice in each of the key business domains you manage: strategy, finance, operations, marketing and human resources. Creating an advisory board lets you tap hard-earned knowledge and advice at a small cost. It’s not complicated. You can convene your board 3 or 4 times a year. Make it worth their while by buying them a really nice dinner. Give them your “state of the business” address and let them provide feedback. One bonus: when you are finally ready to hire managers for these areas, your board members can help you define the role and recommend some candidates.
  • Commit yourself to proactive delegation – Even the best intentioned small business owner can become a bottleneck. You’re good at a lot and you’ve relied on your own wits for so long that you probably have trouble entrusting others. Well, if you’re going to survive beyond the tweens, you need to let go. Make it a game to find one thing a week that someone else can do from now on. Or think about what position you can hire that will relieve your workload, so you can spend more time working “on the business” instead of being mired in it.