Freelancing: The good, the bad and the ugly

At its best, software engineering is fun, challenging and lucrative; at its worst, it's an exercise in frustration and burnout-inducing schedule crunch. Whatever your situation, there will likely come a time when you'll start to question your career choices; invariably, through some combination of external circumstances, changing preferences and simple boredom, you'll want a change. Sometimes that means seeking a promotion; sometimes it means looking for new opportunities, or even a new line of work. And sometimes that means becoming your own boss.

Is freelancing right for you? How does one start a consulting business? What can make or break such a business? A few years back, and following a history of startup and corporate employment, I struck out on my own as a freelance software engineer. I still don't have all the answers, but in this talk I'll do my utmost to help you ask the right questions.

Transcript

1. Freelancing: The good, the bad and the ugly Tomer Gabel Kraków, 15-17 May 2024 // Q&A on https://sli.do #geecon
2. Reckoning 1. On a cold winter’s day late 2020, I was fired I may have deserved it. 2. A few days later, I started my own business … and we’ll explore why and how.
3. This is highly subjective. 1. My personal journey 2. Based on observation and experience 3. May not apply to you! Photo: A delivery truck pours more salt... by SDOT Photos (CC)
4. Know thine enemy Act I
5. Denial [### · · · · · · · · · · · · · · · · · · ] 1/5 1. I knew this was coming I’ve been there before. 2. I still couldn’t figure it out. How did things get so bad? 3. There’s no denying it I was still fired. Photo: Stop by Adan Morgan (CC)
6. Anger [###### · · · · · · · · · · · · ] 2/5 1. I was angry at my employer “It didn’t have to be this way.” Photo: Michael by Ceci (CC)
7. Anger [###### · · · · · · · · · · · · ] 2/5 1. I was angry at my employer “It didn’t have to be this way.” 2. I was angry with my colleagues ”Why wouldn’t they just listen?” Photo: Michael by Ceci (CC)
8. Anger [###### · · · · · · · · · · · · ] 2/5 1. I was angry at my employer “It didn’t have to be this way.” 2. I was angry with my colleagues ”Why wouldn’t they just listen?” 3. I was angry with myself ”Where did I go wrong?” Photo: Michael by Ceci (CC)
9. Bargaining [######### · · · · · · · ] 3/5 I’ve been fired before. This was different though. Was this job different? Was I different? Can I make a better prediction next time? Can I change my behavior to increase my chances?
10. Depression [########### · · · ] 4/5 Alas, no. You can only do your best. My best was not good enough. Can I make a better prediction next time? Can I change my behavior to increase my chances?
11. Acceptance [#############] 5/5 1. I am unemployable Different companies, teams – same result. 2. I don’t even want an employer A newfound wealth of trust issues, yay! 3. I am at the end of my rope Professionally speaking. Photo: Dead End by Michael Sauers (CC)
12. Know thyself Act II
13. Unemployable, then 1. First, need to figure out why. What are my weaknesses? 2. Do these weaknesses always apply? Can I nullify them, or even turn them into strengths? 3. What unique strengths do I bring to the table?
14. Honesty first Situation Expertise Authority “Gravitas” Technical decisions ✓ ? ✓ Architecture ✓ ✗ ? Technical strategy ✓ ✗ ? Process decisions ✓ ✗ ?
15. Honesty first Situation Expertise Authority “Gravitas” Technical decisions ✓ ? ✓ Architecture ✓ ✗ ? Technical strategy ✓ ✗ ? Process decisions ✓ ✗ ? The danger zone
16. Murky authority + Emotional investment = Conflict and frustration
17. Hypotheses 1. Emotional investment is not required Can I do a great job without a personal stake? 2. Emotional investment is counter-productive Hard to be argumentative when you’re not personally affected 3. Gravitas can be artificially created ”Your boss paid good money for me to be here. Take it seriously”
18. Counterpoint 1. An employment contract is a transaction: - Creates personal stake for the employee - Assures trust in the employee 2. Without trust, there’s no leverage 3. Trust is the organizational answer to risk
19. 1. Trust me to do the job they hired me for 2. Trust my professional judgement and advice 3. Trust my professional and business conduct 4. Trust that I have their best interests in mind Customers should be able to:
20. 1. Trust me to do the job they hired me for 2. Trust my professional judgement and advice 3. Trust my professional and business conduct 4. Trust that I have their best interests in mind Customers should be able to: Trust is the real challenge. Can I make it work?
21. ... fight a thousand battles without disaster Act III
22. Plan of attack Bootstrapping • Setup • Legal/admin Marketing • Branding • Pricing Profit! • Work • Invoicing
23. Bootstrapping 1. Pick a name that represents the business Substrate (n): An underlying support or foundation 2. Sort out the basics Licensing, legal (lawyer), admin (CPA), hardware and software 3. Formalize business goals and philosophy
24. Bootstrapping Started with a 2-page “business overview” : • What does it do? • What sets it apart? • Core values Substrate Software Services overview document circa 2021
25. Values, you say? 1. Care 2. Integrity 3. Craftsmanship “We will not, under any circumstances, screw our customers over.”
26. Values, you say? 1. Care 2. Integrity 3. Craftsmanship “We will always be truthful in our dealings. We will never knowingly falsify, misdirect or mislead our customers.”
27. Values, you say? 1. Care 2. Integrity 3. Craftsmanship “Quality matters, inside and out.”
28. Values, you say? 1. Care 2. Integrity 3. Craftsmanship I want my customers to: • Trust me to do the job • Trust my judgement • Trust my conduct • Trust that I have their best interests in mind
29. Values, you say? 1. Care 2. Integrity 3. Craftsmanship I want my customers to: • Trust me to do the job • Trust my judgement • Trust my conduct • Trust that I have their best interests in mind
30. Values, you say? 1. Care 2. Integrity 3. Craftsmanship I want my customers to: • Trust me to do the job • Trust my judgement • Trust my conduct • Trust that I have their best interests in mind
31. Why is branding so important? 1. Your prospective customers don’t know you They’ll try to suss you out regardless of circumstances 2. First impressions are everything You’re not going to get a second chance to impress 3. There are only 24 hours in a day What you pay attention to says a lot about your business!
32. Design brief 1. Design language What do I want to convey? 2. Visual assets Logo, templates etc. 3. Landing site The first thing clients see Substrate Software Services design brief circa 2021
33. The pricing conundrum Hourly rate ✓ Simple to track and invoice ✓ Low risk for both vendor and customer (no commitment) ✗ Linear: work in, money out ✗ Fixed margins Project basis ✓ Easy for customers to plan for ✓ Can improve margins ✗ Estimation is notoriously hard ✗ High risk of budget blowouts/reduced margins
34. The pricing conundrum Hourly rate ✓ Simple to track and invoice ✓ Low risk for both vendor and customer (no commitment) ✗ Linear: work in, money out ✗ Fixed margins Project basis ✓ Easy for customers to plan for ✓ Can improve margins ✗ Estimation is notoriously hard ✗ High risk of budget blowouts/reduced margins
35. How much should you charge? Several factors: 1. The market value of your skills 2. Your reputation 3. How the client values the work 4. The client’s financial situation
36. How much should you charge? Several factors: 1. The market value of your skills 2. Your reputation 3. How the client values the work 4. The client’s financial situation • Your salary as an employee • +40% employer cost (pension fund, health benefits etc.) • Divide by 120 billable hours/month
37. How much should you charge? Several factors: 1. The market value of your skills 2. Your reputation 3. How the client values the work 4. The client’s financial situation • Not much when getting started • Pricing will initially have to reflect that
38. How much should you charge? Several factors: 1. The market value of your skills 2. Your reputation 3. How the client values the work 4. The client’s financial situation • Hard to know when getting started • Hard to gauge with new clients • Unknown in advance so treat it as a filter!
39. Finding your first customer 1. This should come as no surprise: it depends. Your network (friends, colleagues etc.) is invaluable 2. I was lucky (if you call hard work luck…) Organizing/speaking at conferences = professional connections 3. Building a network organically worked for me
40. Epilogue
41. Key Takeaways 1. Freelancing is not for everyone Are you comfortable working alone, being an outsider, taking risks? 2. Know yourself: your skills, flaws, resources Customers respond well to honesty and need predictability 3. There is no one true path to success Try things out, see what sticks!
42. tomer@substrate.co.il @substrate_eng https://github.com/holograph Thank you for listening Questions? Substrate