6 things that can go better in business than you ever expected
When you’re starting a business, bad news and disclaimers are everywhere. But seldom does someone give us good news.
Along my last year and a half entrepreneuring, I’ve cheered big celebrations and weathered troughs of despair. But a few things in business have exceeded my expectations, and there are areas where no one told me it could be better than good. It can be great.
These are my top favorite discoveries from this year, where things turned out better than I’d expected.
- You CAN get incredible support (even from people excited about your business whose smarts and skills in their area are far above yours.)
It seems like every entrepreneurship resource warns the difficulty & necessity of hiring and firing. And yet, so many resources also advise early-stage entrepreneurs to embrace delegation and hire a VA.
After a year, I found myself dropping inbound leads I most wanted to answer — so I buckled up and set out to find a VA.
But what nobody told me is that an assistant wouldn’t necessarily have to be someone I train and mentor step-by-step, as they learn the nuts and bolts of basic projects and do (or fail to do) exactly what I set out for them, in a tightly-scoped project.
Nope — instead, I learned that with sites such as Hire My Mom or The Startup Admin, you can find support for your business that not only allows you to be exactly who you are (without a bunch of pre-work and heavy scoping), but whose expertise is also greater than your own on areas of your business that drive you completely crazy!
It’s not TOTALLY free — being a reasonable person, having a solid handle on who you are, how you work, what your values and needs are, and what you’re wanting really helps.
But my experience on Hire My Mom showed me it is possible to find a true expert in crafting systems and organizations who can help take the pain out of your efforts to manage your emails, leads or payments.
My fear-based visions of VAs as new grads or early-career professionals in a house, trying admirably to connect technical systems with one another (with my same skills gaps and frustration but mercifully more patience) simply weren’t true.
2. A coach is a godsend to keeping you on the right track.
Coaching is this new thing I’d never before heard of. And right out of the gate, I had no intention in investing in it.
But after a few months trying my hand at sales for the first time, I was sick of billing hourly and feeling torn between working at my most efficient and making less money. The broken incentives in billable hours weren’t new to me, but they were painful — and after reading countless Alan Weiss books from the library, I was at a loss for a plan to go from where I was to a better business model, based on project-driven pricing.
Enter Coaching. I’m a voracious reader, so I’m someone who always prefer to check out the freebies and derive all the master plans myself.
But deciding to find and hire a coach, and even saying a big ‘yes’ to an expensive yearlong program, was a gamechanger for me in ways I could have never imagined.
I went from feeling totally isolated on my own island of work to being in the current and flow of a fabulous group of entrepreneurs, all who were investing at the same level to be there — and building businesses that similarly reflected parts of them that they were committed (including financially!) to bringing out to the world in a next-level way.
Investing in a coach isn’t without risk — a great yearlong program can easily run you $10,000 or more, and it can be hard to find a coach you really trust who inspires you and can connect you to your best work.
But overall, even a poor group coaching program can be a game-changer for early stage entrepreneurs. The connections with peers “following the same star” are exponentially valuable, and the advice and accountability true peers have to offer is worth its weight in gold, versus the stuff you find on the street (or, god forbid, from well-intentioned but differently-careered friends and family).
Group coaching changed my life this year.
3. Being a solopreneur doesn’t have to mean working alone.
Countless friends of mine, even some from my group program, grapple with entrepreneurship (in idea and in practice) as a solo sport, feeling drained and alone sitting on their computers and just Skyping from their home.
For me, this year has been proof of the AMAZING community & collaborations possible in San Francisco these days, beyond what you could ever imagine or even see on TV.
Astoundingly generous organizations like the NASDAQ Entrepreneurial Center serve up weekly high-quality entrepreneurial education for free, paired with on-site cafés, where you can meet like-minded people, then apply what you learn together.
Coworking is strangely easy in this city, with not just a large handful of community coworking spaces and communities (i.e. Impact Hub SF), many specifically tailored or supportive of women (check out Double Union or Cava)— but also through San Francisco’s countless Privately Owned Public Open Spaces, some in great, BART-accessible locations with convenient access to food or a good café. (The Dome in Westfield Mall, floor 4, and the POPOS in the LinkedIn Lobby are two of my favorites.)
Finally, community in this city runs deeper than coworkers and space. But more solo work time and a more flexible schedule can free you up as an entrepreneur to engage more deeply with the many organizations and civic collectives this city (still) has to offer. A few of my life-changers have been Michael Markowitz’s charcoal drawing classes at the 23rd Street Studio, summer fun at Camp Grounded and its year-round community, yoga at Integral Yoga Institute and Laughing Lotus — two studios with active kirtans and workshop lineups alongside their normal classes — and exploring a different vibe of intergenerational community through SF’s unique breed of “religious” organizations, many which feel more like radical justice celebrations than like your parents’ Jesus-hailing Sunday boredom-fest (check out the Fire Meditation at the SF Yoga Society, or Sunday morning service at First Mennonite Church of San Francisco inside Congregation Sha’ar Zahav, just one of many clues to its revolutionary and refreshing offering).
4. If something you seek doesn’t yet exist, you can create it!
I remember stalking the whole internet before leaving my prior job at Google, hell-bent on crafting an Impermeable Plan to figure everything out before I left.
The truth is, the World Beyond Your Day Job will not have everything set up in ways that make sense to you, and indeed — many of its current configs may leave you reeling (or wanting to quit, well, most things). There’s a lot of current Suck.
But one thing I didn’t realize is the astounding rewards from Just Fixing It for the problems I faced along the way.
I needed a list of places I could potentially host an entrepreneurs’ workshop! I hired a friend, and we created it.
I wanted a setting where I could apply design thinking & prototyping methods I teach to issues of social justice, especially student loans. I had breakfast with a friend, and we created it. (20+ participants all created something to address student loan exploitation in under 2 hours — 1 even wrote and performed a poem. Amazing!)
After visiting many of the great women’s communities in SF, I still was feeling a lack for a deeper friendship circle among women. A friend came to visit, and we prototyped it with 2 days’ notice on Eventbrite and a get-together in Dolores Park. We created it!
I’m so grateful to the friends I’ve found tea by tea along the way who are SO game to try something weird, new and fun out, and not care (together!) how it ends, as long as we’re Trying it.
And one of the coolest realizations is that when you do something scary, sometimes your experiments gather a following — and attendees write you back asking when the next one will be. (We now have a list of ‘next editions’ to produce when we need a new idea!)
5. Online communities (and learning-focused offline communities) can be really, really useful.
In addition to the people you meet directly through your work, leaving a big company doesn’t have to leave you hungry for people to conspire with who can inspire you forward.
Offline networks like Hive gather global leaders and social entrepreneurs, and leadership classes like Gordon Starr’s create unique communities among their participants and attendees.
Online groups like Wisdompreneurs and the Y Combinator Female Founders’ Conference group are active, lively forums where you can seek advice, real-talk support, and leads for essential services to contract or hire, like bookkeepers or legal advice, or wisdom about what to do in a difficult situation.
Online-Offline networks in the area include Impact Hub SF and Makespace, Jenny Feinberg’s wonderful constantly evolving community for SF’s “creative class” (good news: it’s not exclusive! — if you want that term to apply to you, it can.) :)
Meetups are still the world’s best place to connect around an interest group. And Eventbrite is getting better and better at recommending events happening in your area that are spot-on with what you’re trying to learn.
If you’re hanging on to your corporate life or fearing business for lack of colleagues, check out some of these resources and take a big breath out — it’s all good.
Last, if this slate is still leaving you disconnected, my friend Kira’s book Stop Being Lonely is a super thoughtful resource about how to relax your worries to build closer ties. And Camp Grounded can’t be beat for shaking us out of our old habits and patterned fears.
6. Development-wise, the personal is professional.
Before I started a business, I thought that the most important thing in running a business would be…. business.
Boy was I wrong. As a great friend put it this week, “If you think you’re done on your personal development journey — start your own company.”
This can be a major challenge at first, as running your old business can take you right back to 4th grade in your limbic brain, and remind you of all those old quirks of yours you thought you’d long outgrown.
But this connection works both ways — and, delightfully, the more you grow personally, the more you might find that your business grows too.
For those of us grateful for any chance we can get to lighten our personal loads and heal up old wounds, this comes as a massive relief. Who knew we didn’t have to choose between productivity and prosperity for ourselves and our clients?
Indeed, there are few good resources for unsticking your business like a good therapist and writing practice. If you need a resource, comment below — happy to share recommendations or get you linked up with someone.
