Self Employment / Writing

What I learned from my first 12 months in business

Your first 12 months in business can both drag and fly by.

With all of its ups and downs and swings and roundabouts, you will love it, hate it, overwork, underwork, find yourself, lose yourself, and most importantly, learn a hell of a lot about how you want to run your business and who you want to work with.

After a lot of reflection, here are my key learnings from my first 12 months in business. I hope they help you!

1. It’s all about the contract

I’m going to be blunt.


Think of a contract as a security blanket for you and your client. Even if it seems like the stars and the moon have aligned to bring you and your new client together for what seems like the start of a beautiful working relationship, hit pause and draw up a contract you are both comfortable with.

Trust me.

You won’t regret it.

Note: a contract can also be called an Agreement, Terms and Conditions, etc.

2. Build a probationary period into your contract

By building a probationary period into your contract, you are establishing your first official review point to check on how the working relationship is tracking, assess whether something needs to be changed or tweaked and reassess the scope of the contract.

You never know – it might just lead to increased work!

A probationary period can safeguard you and your client in the instance that the job is turning sour. 

Perhaps there is a difference in personalities or working style, or the job has turned out to be bigger than Ben Hur, and you admit that you’ve taken on more than you can chew. Or perhaps you are just not enjoying the work. This is a great way to ‘break up with each other’ early whilst redeeming the relationship.

3. Don’t dis the small jobs.

They could become your biggest client and main money earner. OR they could refer you to your biggest client or money earner.

As one does not judge a book by its cover, don’t dismiss the small jobs. Some of my smallest jobs have led to referrals and my best clients.

4. Grow some balls and ask for payment in advance

It’s within your right to request payment or a % amount in advance, as long as all parties agree and it’s clearly stated in your Terms and Conditions, Contract or other documentation.

This is a great way to safeguard you from clients who go missing halfway through a job, who refuse to pay, or, in the case of a job taking months to complete for one reason or another, you have some money in the kitty to survive on (no, you can’t survive on air!).

This is something I clocked on too late in the piece and wish I had given it more thought from the start. Being naive and new to my business, I was reluctant to ask for payment in advance but quickly learned my lesson after several late payments and non-payments, resulting in a large degree of financial stress.

5. Sometimes it’s better to cut your losses and RUN!

After months of working with a client who expected the world, communicated horribly, and paid late (and in the end, not at all), I ended our working relationship AFTER sticking with it longer than I should have because of the opportunity the job had presented and because I wanted to build up my portfolio. I stopped working with them in November 2014, and after many ‘pay now’ letters, I am still owed money. The financial and emotional stress this caused was unbelievable. Yes, I could have pursued debt collection measures, but I decided to cut my losses to live and learn by weighing up the money that lengthy exercise would cost me.

* This is also where I learned lesson #12.

6. Working from home is a lot harder than it seems

See my post on Working from Home for some comprehensive tips and tricks I’ve picked up over the last 12 months of working from home. I  went slightly stir-crazy for a time, being low on funds and feeling housebound and isolated!

7. Self-care is critical

You are your business, and self-care is critical to the success of your business and your ongoing mental and physical health. Ensure you eat well, are hydrated, get enough sleep, and fit in time for regular movement/exercise and fun. Keep your stress levels in check, and make sure you have a support network you can call on in times of need for advice, a coffee break, a rant, a cry, or a laugh.

8. It’s not all about them

You want to get out there and build your network, and you want people to like you.

You want to land that deal and please your client. You want it all, and you will traverse all over town and beyond five times before collapsing in a heap in the office or home to start your real work for the day.

What you need to acknowledge is that it’s not all about them. It’s about you too.

There is nothing wrong with saying no or asking people to come to you, meet you halfway, or hold virtual meetings. 

I also highly recommend having one meeting-free day a week. I go as far as to block my calendar out for one day a week to help me focus on what needs to be done.

9. Schedule time with your loved ones

It’s common when starting a business for your loved one/s to feel neglected by the other.

It sounds terrible, doesn’t it?

I recommend scheduling some regular quality time with your respective other and even stopping work when either of you gets home, even if it is just for a 30-minute cuppa and a ‘how was your day, what did you do’ chat. This will help both you and your relationship and business.

10. Backup your computer, devices AND portable hard drives

I learned this the hard way after losing almost a lifetime’s worth of photos and work (only a few months into my business, THANK GOD!) because my external hard drive corrupted as I was trying to back up my laptop after a lengthy period of time.

Lesson learned.

Back up your laptop, devices and external hard drive regularly before updating any software.

I may turn into a compulsive back-upper yet…

11. There’s no harm in taking a part-time job

Some will tell you that taking a part-time job will distract you from your business and that to start a business, you need to be ‘all in’.  

Yes, it’s a great thought, but none of us is superhuman, and we all have to live.

Some of us don’t have the luxury of quitting our day jobs to start our own business with a nest egg to support us through our embryonic stage.

Ease up the pressure on yourself and your family by taking a part-time job that provides security to help you through the startup phase, even if it’s stacking shelves at the local supermarket. 

I was oblivious that this is exactly what many small business owners do!

How stupid did I feel after months of working my ass off, stressing myself silly over money and chasing clients whilst needing to pay the mortgage and other bills and trying to prove to myself that I could do this all by myself?

Do not underestimate the stress and pressure associated with the financial stress of starting a business. Getting a part-time job was the best thing I ever did (after quitting my career in project management) – for both my partner and me.

12. Listen to your gut

Listen to what your body is telling you, especially when your gut sends you some strong signals against taking a job or committing to working with someone.

You didn’t go into business for yourself to hate what you do!

Remember, It’s your business, and you don’t have to say yes to every job or client.

13. Don’t undervalue yourself

Don’t undervalue yourself.

I’ve heard this so many times, but most of us do. I’ve done it over and over (to build up my portfolio…that’s my excuse!).

Review your rates every 3-6 months. Research what others in your niche are charging. Ask others the question. Identify your differentiating factor. You are probably worth more than you think!

14. Don’t underestimate word of mouth

Word of mouth can be more successful than online marketing and attending networking events [Frame that…those words came from the fingers of a social media marketer and blogger!].

A business may start slow, but it will pay dividends by putting in the hard yards, doing a good job every time, and being authentic.

Today, most of my work comes via word of mouth or referrals. I’m now blessed to have the opportunity to work with like-minded people in the niche areas I am passionate about.

See #3 and #12, as they were key factors leading me to this point.

15. Keep your options open

My business has morphed a few times over the last 12 months.

I started focusing on life coaching, then gravitated to freelance writing, followed by virtual assistance work. My focus then moved to social media and blog consulting.

I still have a way to go, but I am pleased that I didn’t listen to certain experts earlier on who advised I should ‘lock myself into a niche’.

By not doing this, I allowed myself the time to go through a process of self-discovery and learning, one in which I have grown and changed – oh, and learned a hell of a lot!

What are your startup lessons learned? I’d love to hear them.

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About Author

Changed careers in my 30's. Became a freelancer writer & marketer. I'm a proud redhead, fangirl, wife & step mum. And I'm a lover of all things books, movies, podcasts, dogs & naps.

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