This post has been a long, long time coming.

First, I’m not going to drag out any dirty laundry or any of that stuff. There’s enough on that on the internet as it is, and I don’t really want to add to the pile. Some stuff should stay unsaid.

But I am going to share a few key things about my misadventures in entrepreneurship, career confusion, and how I’m getting myself back on track as well as what I’ve learned in the process.

Because it might help someone else, and it will certainly help me.

The Exit

Some of you may remember back in 2011, Radian6 (my company at the time) was acquired by Salesforce.com. It was an exciting time, but all along I had known that if we exited, I didn’t really have desires to work for a large company.

A friend and colleague of mine at the time talked at length about what we thought businesses were missing when it came to social media proliferation and operational adoption in their businesses. So we conceived of a consulting firm to offer that sort of guidance and programs in the form of advisory work, workshops, and strategy centered around the change management required. I left my role at SFDC, he retired his clients at his IT consulting business. So was born SideraWorks.

Everyone is always curious about how these acquisitions go down. There were rumors that I was ridiculously wealthy then, even one that I’d bought some ridiculous piece of property in the tropics. I laughed at those. 🙂 (Where do people come up with these things?)

The truth is that I did well, but not millions, more like comfortable lower six figures in the exit. Very rewarding, a bit overwhelming, but comfortable.

I share that very personal tidbit to help quash some of the curiosity and hype for a reality check as well as lead relevantly into the next phase of my story.

The Adventure

Starting a business is really hard. Keeping one going is even harder.

I had stars in my eyes, adventure in my head, and was incredibly optimistic (read: naive) about what I was getting into. Because I was so eager and convinced this was the right track, I was more than willing to bankroll this entrepreneurial adventure with my newfound financial freedom (read: stupidity, no matter how savvy I thought I was), because it seemed inevitable that I’d get it back and then some when the business got off the ground.

Granted, I spent some money on personal things – fixing some stuff up around the house, taking about six months off to take a break and plan the business, taking some personal trips to beautiful places to recharge and relax.

But mostly, my resources were aimed at building up this fledgling firm, and that was my personal commitment to the business.

We had several planning sessions about SideraWorks, complete with post-it notes on walls and scribbles on big easel pads and pacing back and forth in my dining room or in a hotel room spouting ideas about programs and offerings and business structure and all the things we were confident we could do.

We had some early interest, a few connections from friends and our professional networks…and off we went to try to conquer the world through social business.

The Misadventure

The trick about bootstrapping a business is that you realize how much everything costs, and quickly.

Website design, even when you do it on the cheap (and inevitably break something and have to hire an awesome firm to fix it for you). Identity design.

The travel to conferences, now on your own dime, to network and prospect and speak, the lifeblood of many an entrepreneur.

The travel to see prospects and do pitches, also on your own dime.

And even though we didn’t have office space, we both had living expenses that needed to be paid, and then there’s infrastructure like errors & omissions insurance, legal fees and guidance, accounting, mailboxes, phone routing, materials for workshops…the list goes on. And it always grows.

And while the money kept going out from my bank account…for almost three years…the business didn’t keep coming in.

There are so many reasons for that, including:

  • Neither my business partner nor I were focused on business development, no matter how good we were at keeping the clients once we had them. We both wanted to be creating ideas and strategy and methodologies. Keeping the pipe full was our nemesis.
  • I got VERY sick in the second year of our business, basically putting me out of commission for months on end while I sought diagnosis and got treatment (I’m fine). That sure didn’t help the above.
  • We didn’t really understand the market for our offerings as well as we thought we did, and that showed early on even as we denied it for a while.
  • Related, we simply overestimated the demand for what we were providing. Customers were confused by our offerings, not at the right maturity point, and were actually shopping for things we thought we were “too good” to provide, like 101 level social media guidance.
  • Once you realize you need to pivot — which we eventually did, sort of —  you still need to fund the pivot while you move things around and build the revised business. Every time I moved money from my accounts to the business account, I worried. Because that balance was finite, and dwindling.
  • We didn’t identify the crisis point early enough; I could have stopped throwing good money after bad much earlier, but I didn’t. I was afraid to be seen as giving up, afraid to admit that I was failing, afraid of so many things. I didn’t say stop until I had put myself in a precarious situation.

You get the point.

We did have a few really amazing clients and super interesting projects that I loved working on. Those are relationships I still have to this day.

The trouble is, the income wasn’t in line with the outgo. Not by a long shot. And we differed drastically on how to right the ship. You can lecture me all day long about what we could and should have done differently, and I’ve certainly had those conversations with myself many, many times. The reality remains: we didn’t.

Eventually I ran out of money, and therefore the business ran out of money, and I made the decision to leave SideraWorks behind and find another opportunity to put the pieces back together while my partner chose to keep the SideraWorks brand and try to make a go of it solo (SideraWorks was apparently “acquired” earlier this year by Crowdsource).

The Fallout

This is a story you’ve heard a thousand times before.

Failure. Man, does it hurt. In so many ways. It’s actually really hard to put into words how devastating it can be.

I paid for the failure of my business:

Financially: Everything I’d made in the acquisition was gone three years later and then some in the form of family loans and significant credit card debt I accrued that was never repaid by the business, just to avoid foreclosing on my mortgage.

Personally: I completely severed the relationship with my partner who had once been my closest friend, in a very messy and difficult fashion, and in the process, lost many other friendships, as well as lost a LOT of time with my family and my daughter – and I’d already been limited as a single mom – and what few friends I still had.

Professionally: I put so much into the business that I neglected to keep up my successful personal platforms online, ignored lots of relationships, and missed opportunities that I would have otherwise jumped on. When it got bad, I was too embarrassed to reconnect, afraid of giving explanations I wasn’t sure I had.

Health-wise: I sank into a deep, deep depression, gained weight, fought constant and chronic illness, daily panic attacks, hospitalization, and utterly lost most of my sense of self-worth in the process. The entire thing completely shattered my confidence, and I pretty much didn’t leave my house for the last months as everything unraveled.

In a nutshell, three years after my bright-eyed dive into this future, I was broken. In all aspects of the word.

It was, by far, the worst I’ve ever felt in my life.

The Redemption

I have to admit, I got lucky.

In the midst of the epic fallout that was a whole-life failure, I started sheepishly poking around with friends and professional contacts — some of whom hadn’t heard from me for months — in order to try to mend some connections and ask for help with hat in hand, ashamed of my failures.

Lucky for me, 80% of them were incredibly gracious, glad to hear from me, and more than happy to help as I sought to build my life back up by taking a professional position with an established company.

Not too long after, I got a call from a recruiter looking to fill a marketing leadership role with Sysomos, a perfect role for me in many ways (and it’s the job I’m fortunate to now hold, a bit more than one year to the day later).

I flew to that job interview less than 36 hours after being discharged from the hospital with pneumonia and exhaustion, but I went anyway, and tried to find my old self again if for a few hours, and after a series of fourteen interviews across two weeks…I was thrilled to be offered the job.

(Someone, somewhere was looking out for me, but definitely made me earn it.)

I’m happy to say that since then – a year and five days after I started that job – I’ve slowly put many of the pieces back together.

I’ve mourned the relationships that I lost (maybe some of which I never really had in the first place, which is a hard enough lesson to learn in itself).

I’ve started to recover financially, though that will be a very (very) long road and I’ll never recover the financial position I had after the Radian6 acquisition. I still have approximately $15,000 in business-related debt on credit cards that I have yet to pay off, and some tax issues I am still unraveling. It’s not much as compared to where it was, but it’s enough to leave a cloud over my head most days. And my credit rating will likely take years to recover.

I’d like to think I’ve found a better place professionally, not only through my amazing job at Sysomos (which I truly love, especially because of my incredible team) but because I understand now what I’m good at, and what I’m not. And I’m incredibly happy to be excelling there instead of trying to be something and somewhere I really don’t belong.

Health-wise, I’m getting there. A lot of therapy, still. Medication. Rest and recharge time. Ups and downs and everything in between. I have significant weight yet to lose from repeated illness, medication and depression, but I’m active and out there again, coming off meds one at a time, and I’ll figure that out eventually.

I’m also pursuing hobbies – I have a horse and returned to riding (with my daughter!) which is my first-ever love, started doing more reading and calligraphy again, practicing music – and spending time with my beloved daughter and family in much much larger quantities.

I set limits for work hours unless absolutely necessary and am – I think once and for all – putting behind me that the only way to be successful is to work more hours than the next person and put it all on the line for your career.

I’m writing again. I don’t know quite where it will take me yet, but I’ve missed it.

I’m on the other side, I’m happy to say. But make no mistake: I was very close more than a couple of times to wondering whether it was all worth it any more, and whether I wasn’t just a waste of space myself. My sister, my mom and my daughter kept me alive, quite literally. Maybe they don’t know it. Maybe they never need to.

And that’s all I’ll say about that for now.

[If you or someone you love is in need of crisis help or counseling, the National Suicide Prevention Lifeline is 1-800-273-TALK. Please call. And don’t wait.]

What did I learn?

I think I have enough distance from it all now to try and articulate a few of the things I took away from this experience.

My personal learnings:

1. I don’t enjoy being an entrepreneur. And that’s really okay. I like working for an established (even if young!) company because I am an incredible execution person. Give me some great leadership and a big vision, and I’ll make it happen all day long. There is a place for people like me, and now that I know that, I can pursue it without the guilt of rejecting the glamorization of entrepreneurship that we seem to hear and see at every turn.

2. I am really great at being on the execution side of things. And I am a marketer, through and through, and I actually love sales. I used to think that wasn’t good enough (sorry marketing people) for some reason. That to be “worthy” and to be valued and to have my ideas heard meant I had to be a consultant or advisor or business owner or in some Special Crowd or another that I just didn’t belong to.

3. I was really arrogant about what I knew, and what I thought others should know. For some reason, all the knowledge I have about knowing your market and customer vaporized when I had this business idea that was MINE. I was so excited about working with a friend (don’t do that; trust me) and so sure our ideas were better than anything out there that I managed to blind and deafen myself to the realities and the research that told me that there simply wasn’t a market for what we wanted to do.

4. Be very careful about the risks and investments you’re willing to make. I invested way too much, financially and personally, in the whole thing. Get a good lawyer, be dispassionate about business terms, protect yourself, be conservative with your money and listen to people smarter than you. Most of them learned from the scars they have. I should have listened to a lot of people I trusted, and listened to them much sooner.

5. Every human has their breaking point. Because I’m outspoken. Because I’m an “oversharer”. Because I can come across as confident and opinionated and well-adjusted and have had moments of success, some of which I never asked for. All of those are just part of the reason why almost every single person disappeared at my most acute time of crisis…maybe assuming I had it all handled like the tough girl I appeared to be? Maybe because I pushed them away?…and why I learned that I am as human, vulnerable, and worthy as any other person out there.

I don’t have to have anyone’s approval to tell my story anymore, even if if makes people uncomfortable. Even if my story is messy and imperfect.

This is my truth. And I will own it. Always.

So, that’s what I’ve got to offer. If you have other questions, I’m more than happy to try and answer them. If you’re not comfortable doing so publicly in the comments, hit me up at amber@brasstackthinking.com. I’d love to talk to you.

I know it’s just one more story of a business that didn’t make it and a would-be entrepreneur that bears the road miles, but this one is mine, and that makes it so much more visceral to me. It was something I had to share in order to close the door on some things once and for all.

I hope maybe that my experience helps you feel less alone, less flawed, less like you aren’t doing the right things, less like everyone but you is succeeding where you are not. Maybe it helps you with the stuff you’re wrestling with right now. Maybe it’s a glimpse at the reality that not very many people show you.

And more than anything, I want you to know that no matter what, there is light on the other side.

You are strong. And capable. And resilient. And courageous. We all are, in our own ways, and somehow whatever the mountain rains down on us, I pray that we always find the constitution to dig through the rubble.

If I can make it through and come out the other side stronger than ever, I believe anyone can.

To those of you who have been here since the start, thank you. To those of you who have been with me since and believed in me enough to give me a chance for the first time or again, thank you, too. For those of you I lost along the way…well…perhaps it’s better, that. I wish you well.

And to those who never doubted for a minute that I’d come through and find the other side, I owe you more than you could ever know.

The future is yet unwritten. And my pen is sharp.

Onward!