The First 100 Days … Going Out On Your Own

Deborah Sloan
5 min readNov 24, 2021

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Image by Author - What Is The Script?

I had a mini crisis recently¹. I realised I was already three months into this adventure, the ‘career break’ where I imagined I’d step effortlessly out of my old life and into my new one. Back in the summer, I was excited about the opportunity to chart my own path, captain my ship, become ‘Director of Myself’, autonomous and free. I’d have capacity and energy to figure out what I wanted to do next, to explore interesting projects, to create, curate and cultivate. I’d action lots of initiatives, see ideas come to fruition. I’d make such a difference to the world. On the way, I’d find me.

But it hasn’t been like that at all. It’s been frustrating and confusing and disorientating and at times, strangely depleting. If only I could sing, I’d be screeching à la Adele - “I had good intentions and the highest hopes”²…

My best excuse is that I’m never good with Novembers. When the clocks go back and the nights draw in, I lose all enthusiasm to leave the house. I slump in a heap, crave cake, sticky toffee pudding, sleep and February. Usually, it takes a couple of weeks for my system to adjust. This November was so much harder, my mood dived, I didn’t have anywhere to go, there was little to coax me out.

I questioned what I had to show for my first 100 days? Could I name achievements, milestones, successes?

My first 100 days have more than been and gone. I’m around 116 days in now and if I’m honest, quite a few of these have been spent staring blankly at the wall. Everything is a huge learning curve and so tediously slow - registering a company, opening a bank account, editing a website, navigating legalities, designing a newsletter. Having spent hours integrating Calendly, I asked my husband to test it. Let’s just say, I was just a tad put out when he opted for a fifteen-minute appointment³.

In calculating how long I’ve been ‘out on my own’, I reckoned I probably shouldn’t count August as I was both physically and mentally on holiday for most of it. Problem is I have been taking mental holidays on Mondays and Fridays, then Tuesday afternoons and quite often extensive chunks of Thursday. I can’t understand though why I never have any time and it’s always teatime.

I have become increasingly conscious of my lack of coherent purpose and how without title, position or standing, I can easily drift, doubt and lose my confidence. I recognise how institutionalised I was, how much I measured my worth through an email inbox and invites to meetings. Now, the days can descend into monotony. I am sick of back-to-back tea and coffee. Even the children don’t seem to need me anymore. I seek out domestic challenges - our cupboards sparkle, the cutlery drawer is crumbless, the spice jars have been aesthetically re-organised, most of my wardrobe has been recycled on eBay. I trawl the bedrooms looking for abandoned laundry. I’ve even been to the spa⁴! As we sit over a leisurely freshly-ground coffee and home-made granola⁵ in the mornings, our conversations usually go something like this, “So what’s your plans for today?” (me to him). “I’m speaking on a panel at a CEO summit. What about you?” (him to me). “I’m going to research Christmas baubles”.

At one point in early September, I decided I’d just throw myself wide open to anything and everything. I’d follow any gut instinct or random notion. Why not officially launch my career break, I thought? It might bring clarity. No-one knew why they were coming to my garden, but yet, they came. As I recall that evening, I want to weep. It was kind of Field of Dreams. I drank fizzy stuff and ate canapés. It felt like people still believed in me.

I have tried to establish a business, focusing on diversity and inclusion. I’m terrible at it. I’ve faced rejection. I don’t have a business head nor any business acumen. Business plans suck my soul. Financial forecasts scramble my brain. There are so many different types of insurance so I don’t get sued. When I am asked how exactly I intend to make money, I have no idea. I’m not sure following my heart is going to make my fortune. “What will people pay for?” I asked. “What keeps them awake at night,” was the reply. I’m not sure that’s what I want to capitalise on.

Being your own boss sounds so liberating but in reality, it’s so lonely. With no colleagues, team, or deadlines, you are solely responsible for initiating, progressing and finishing. The hard fact is, no-one cares if you even get out of bed. It’s rare to find all the skills required to be successful at this in one body. I’ve had to motivate, praise and reward myself. I want to apologise for the extensive amount of my musings that have dropped into inboxes or filled up social media feeds. It’s all I currently believe I can do. When I write, I can at least see a finished product. I hate to admit it but ‘likes’ equal validation and I am learning how much any bit of encouragement matters.

When I started out on this journey, I said I would share the realities. Many of us have that urge to step out on our own, to make a career change, to try an alternative trajectory, to launch a new venture. But it’s tough. I was under-prepared. I chose a one-year career break so I had a back-up plan. But, when you fill out a form, stop your salary and leave, the risks are immense. If this fails, I don’t know what I will go back to. My organisation has moved on without me. No manager is keeping in touch. I am not sure I want to return to my old life. That’s a lot of pressure.

Ultimately, I can’t do this alone, no woman is an island. I have to quell those fears that I am turning to mush and losing my professional credibility, that maybe the grass isn’t greener out on your own, so I’m going to end with two invitations.

(1) If you are having similar experiences, and would like some company, I am ALWAYS available for coffee. If nothing else, it gets me out of the house…

(2) If you know how to mould my heart for people, my love of words and my desire for a better, fairer world into something useful and would like to work together, I’d be very keen to chat…

[1] It’s probably ongoing - you can tell me after reading this…

[2] Bingo! Been trying to get these lyrics into a piece for ages!

[3] Other (much) longer options were available. N.B. I cancelled his appointment.

[4] You can read more on this at https://dj-sloan.medium.com/the-spa-does-anyone-actually-enjoy-it-d3c9ef1a0677

[5] I made all of this bit up. It’s called poetic licence.

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Deborah Sloan
Deborah Sloan

Written by Deborah Sloan

I am no longer publishing here but am now on Substack at https://deborahsloan.substack.com. I write about leaving things in midlife. Book out March 2025.